Christmann, M. et al.: 2020 Science of Synthesis, 2020/1: Knowledge Updates 2020/1 DOI: 10.1055/sos-SD-116-01081
Knowledge Updates 2020/1

16.17.7 Purines (Update 2020)

Weitere Informationen

Buch

Herausgeber: Christmann, M.; Huang, Z.; Jiang, X.; Li, J.-J.; Oestreich, M.; Petersson, E. J.; Schaumann, E.; Wang, M.

Autoren: Bode, J. W.; Cabrera, M.; Howlader, A. H.; Huang, Z.; Liang, Y.; Liu, G.; Maison, W.; Ohe, K.; Okamoto, K.; Osuna Gálvez, A.; Wen, Z.; Wnuk, S. F.; Wu, F.; Zhu, S.

Titel: Knowledge Updates 2020/1

Print ISBN: 9783132435582; Online ISBN: 9783132435605; Buch-DOI: 10.1055/b000000102

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Knowledge Updates



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Typ: Mehrbändiges Werk

 


Abstract

This chapter is an update to the earlier Science of Synthesis contribution (Section 16.17) describing methods for the synthesis and chemical modification of purine and purine derivatives. It focuses on the literature published in the period 2002–2019, with a particular emphasis on regioselective direct C—H functionalization of purines, transition-metal-catalyzed cross-coupling reactions of halopurines, and synthesis of purine analogues, including azidopurines, by exchange of substituents.

 
  • 1 Fischer E. Ber. Dtsch. Chem. Ges. 1898; 31: 2550
  • 2 Szatylowicz H, Jezuita A, Marek PH, Krygowski TM. RSC Adv. 2019; 9: 31 343
  • 3 Scheele CW. Opuscula 1776; 2: 73
  • 4 Pedley AM, Benkovic SJ. Trends Biochem. Sci. 2017; 42: 141
  • 5 Vardanyan R, Hruby V. Synthesis of Best-Seller Drugs. Academic Press; Boston 2016: 495
  • 6 Legraverend M, Grierson DS. Bioorg. Med. Chem. 2006; 14: 3987
  • 7 Miller DC, Klute W, Brown AD. Bioorg. Med. Chem. Lett. 2011; 21: 6108
  • 8 Spina D. Br. J. Pharmacol. 2008; 155: 308
  • 9 Liu Q, Thoreen C, Wang J, Sabatini D, Gray NS. Drug Discovery Today: Ther. Strategies 2009; 6: 47
  • 10 Sharp S, Workman P. Adv. Cancer Res. 2006; 95: 323
  • 11 Pineda de las Infantas y Villatoro MJ, Unciti-Broceta JD, Contreras-Montoya R, Garcia-Salcedo JA, Gallo Mezo MA, Unciti-Broceta A, Diaz-Mochon JJ. Sci. Rep. 2015; 5: 9139
  • 12 Montgomery JA, Shortnacy-Fowler AT, Clayton SD, Riordan JM, Secrist III JA. J. Med. Chem. 1992; 35: 397
  • 13 Bonate PL, Arthaud L, Cantrell Jr WR, Stephenson K, Secrist III JA, Weitman S. Nat. Rev. Drug Discovery 2006; 5: 855
  • 14 Zhang Y, Secrist III JA, Ealick SE. Acta Crystallogr., Sect. D 2006; 62: 133
  • 15 Kim W, Le TM, Wei L, Poddar S, Bazzy J, Wang X, Uong NT, Abt ER, Capri JR, Austin WR, Van Valkenburgh JS, Steele D, Gipson RM, Slavik R, Cabebe AE, Taechariyakul T, Yaghoubi SS, Lee JT, Sadeghi S, Lavie A, Faull KF, Witte ON, Donahue TR, Phelps ME, Herschman HR, Herrmann K, Czernin J, Radu CG. Proc. Natl. Acad. Sci. U. S. A. 2016; 113: 4027
  • 16 Parker WB. Chem. Rev. 2009; 109: 2880
  • 17 Pertusati F, McGuigan C. Chem. Commun. (Cambridge) 2015; 51: 8070
  • 18 McGuigan C, Murziani P, Slusarczyk M, Gonczy B, Vande Voorde J, Liekens S, Balzarini J. J. Med. Chem. 2011; 54: 7247
  • 19 McGuigan C, Derudas M, Bugert JJ, Andrei G, Snoeck R, Balzarini J. Bioorg. Med. Chem. Lett. 2008; 18: 4364
  • 20 Derudas M, Carta D, Brancale A, Vanpouille C, Lisco A, Margolis L, Balzarini J, McGuigan C. J. Med. Chem. 2009; 52: 5520
  • 21 Jacobson KA, Müller CE. Neuropharmacology 2016; 104: 31
  • 22 Hauser AS, Attwood MM, Rask-Andersen M, Schiöth HB, Gloriam DE. Nat. Rev. Drug Discovery 2017; 16: 829
  • 23 Jacobson KA, Tosh DK, Jain S, Gao Z.-G. Front. Cell. Neurosci. 2019; 13: 124
  • 24 Jacobson KA, Gao Z.-G. Nat. Rev. Drug Discovery 2006; 5: 247
  • 25 Norgard NB, Hann CL, Dale GL. Clin. Appl. Thromb./Hemostasis 2009; 15: 177
  • 26 Jacobson KA, Klutz AM, Tosh DK, Ivanov AA, Preti D, Baraldi PG. Handb. Exp. Pharmacol. 2009; 123
  • 27 Tosh DK, Rao H, Bitant A, Salmaso V, Mannes P, Lieberman DI, Vaughan KL, Mattison JA, Rothwell AC, Auchampach JA, Ciancetta A, Liu N, Cui Z, Gao Z.-G, Reitman ML, Gavrilova O, Jacobson KA. J. Med. Chem. 2019; 62: 1502
  • 28 Rosemeyer H. Chem. Biodiversity 2004; 1: 361
  • 29 Kozhevnikov DN, Kozhevnikov VN. Prog. Heterocycl. Chem. 2009; 21: 415
  • 30 Mondal M, Begum T, Bharali P. Catal. Sci. Technol. 2018; 8: 6029
  • 31 Palladium-Catalyzed Modification of Nucleosides, Nucleotides and Oligonucleotides. Kapdi AR, Maiti D, Sanghvi YS. Elsevier; Amsterdam 2018
  • 32 Seley-Radtke KL, Yates MK. Antiviral Res. 2018; 154: 66
  • 33 De Clercq E, Neyts J. Handb. Exp. Pharmacol. 2009; 53
  • 34 Jordheim LP, Durantel D, Zoulim F, Dumontet C. Nat. Rev. Drug Discovery 2013; 12: 447
  • 35 Shallop AJ, Gaffney BL, Jones RA. J. Org. Chem. 2003; 68: 8657
  • 36 Chang L, Lee S.-Y, Leonczak P, Rozenski J, De Jonghe S, Hanck T, Müller CE, Herdewijn P. J. Med. Chem. 2014; 57: 10 080
  • 37 Szczepankiewicz BG, Rohde JJ, Kurukulasuriya R. Org. Lett. 2005; 7: 1833
  • 38 Hammarström LGJ, Meyer ME, Smith DB, Talamás FX. Tetrahedron Lett. 2003; 44: 8361
  • 39 Hammarström LGJ, Smith DB, Talamás FX. Tetrahedron Lett. 2007; 48: 2823
  • 40 Susvilo I, Brukstus A, Tumkevicius S. Tetrahedron Lett. 2005; 46: 1841
  • 41 Dang Q, Rydzewski RM, Cashion DK, Erion MD. Tetrahedron Lett. 2008; 49: 2143
  • 42 Rico-Gómez R, López-Romero JM, Hierrezuelo J, Brea J, Loza MI, Pérez-González M. Carbohydr. Res. 2008; 343: 855
  • 43 Zhong Q.-F, Sun L.-P. Tetrahedron 2010; 66: 5107
  • 44 Boeck BD, Jiang S, Janousek Z, Viehe HG. Tetrahedron 1994; 50: 7075
  • 45 del Carmen Ruiz Ruiz M, Vasella A. Helv. Chim. Acta 2011; 94: 785
  • 46 Morel B, Franck P, Bidange J, Sergeyev S, Smith DA, Moseley JD, Maes BUW. ChemSusChem 2017; 10: 624
  • 47 Maes J, Rauws TRM, Maes BUW. Chem.–Eur. J. 2013; 19: 9137
  • 48 Senhorães N, Dias AM, Conde LM, Proença MF. Synlett 2011; 181
  • 49 Wesch T, Iaroshenko VO, Groth U. Synlett 2008; 1459
  • 50 Iaroshenko VO. Synthesis 2009; 3967
  • 51 Iaroshenko VO, Ostrovskyi D, Petrosyan A, Mkrtchyan S, Villinger A, Langer P. J. Org. Chem. 2011; 76: 2899
  • 52 Liang Y, Wnuk SF. Molecules 2015; 20: 4874
  • 53 Liang Y, Wnuk SF, In: Palladium-Catalyzed Modification of Nucleosides, Nucleotides and Oligonucleotides Kapdi AR, Maiti D, Sanghvi YS. Elsevier Amsterdam 2018; 197
  • 54 Gayakhe V, Sanghvi YS, Fairlamb IJS, Kapdi AR. Chem. Commun. (Cambridge) 2015; 51: 11 944
  • 55 Wang D.-C, Xia R, Xie M.-S, Qu G.-R, Guo H.-M. Org. Biomol. Chem. 2016; 14: 4189
  • 56 Xia R, Niu H.-Y, Qu G.-R, Guo H.-M. Org. Lett. 2012; 14: 5546
  • 57 Fontana F, Minisci F, Barbosa MCN, Vismara E. Acta Chem. Scand. 1989; 43: 995
  • 58 Désaubry L, Bourguignon J.-J. Tetrahedron Lett. 1995; 36: 7875
  • 59 Xia R, Xie M.-S, Niu H.-Y, Qu G.-R, Guo H.-M. Org. Lett. 2014; 16: 444
  • 60 Sherwood TC, Li N, Yazdani AN, Dhar TGM. J. Org. Chem. 2018; 83: 3000
  • 61 Li G.-X, Morales-Rivera CA, Wang Y, Gao F, He G, Liu P, Chen G. Chem. Sci. 2016; 7: 6407
  • 62 Pitre SP, Muuronen M, Fishman DA, Overman LE. ACS Catal. 2019; 9: 3413
  • 63 Caronna T, Fronza G, Minisci F, Porta O. J. Chem. Soc., Perkin Trans. 2 1972; 2035
  • 64 Tian M, Yu M, Shi T, Hu J, Li S, Xu J, Chen N, Du H. Eur. J. Org. Chem. 2017; 3415
  • 65 D’Errico S, Piccialli V, Oliviero G, Borbone N, Amato J, D’Atri V, Piccialli G. Tetrahedron 2011; 67: 6138
  • 66 Niu H, Su L, Li J, Guo H, Wang D, Xie M, Qu G. CN 104 478 883, 2015
  • 67 Niu H.-Y, Su L.-Y, Bai S.-X, Li J.-P, Feng X.-L, Guo H.-M. Chin. Chem. Lett. 2017; 28: 105
  • 68 Tan KL, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2002; 124: 13 964
  • 69 Tan KL, Park S, Ellman JA, Bergman RG. J. Org. Chem. 2004; 69: 7329
  • 70 Nakanowatari S, Müller T, Oliveira JCA, Ackermann L. Angew. Chem. Int. Ed. 2017; 56: 15 891
  • 71 Xin P.-Y, Niu H.-Y, Qu G.-R, Ding R.-F, Guo H.-M. Chem. Commun. (Cambridge) 2012; 48: 6717
  • 72 Sahnoun S, Messaoudi S, Peyrat J.-F, Brion J.-D, Alami M. Tetrahedron Lett. 2008; 49: 7279
  • 73 Vabre R, Chevot F, Legraverend M, Piguel S. J. Org. Chem. 2011; 76: 9542
  • 74 Sahnoun S, Messaoudi S, Brion J.-D, Alami M. Eur. J. Org. Chem. 2010; 6097
  • 75 Lagisetty P, Zhang L, Lakshman MK. Adv. Synth. Catal. 2008; 350: 602
  • 76 Čerňa I, Pohl R, Klepetářová B, Hocek M. Org. Lett. 2006; 8: 5389
  • 77 Lakshman MK, Deb AC, Chamala RR, Pradhan P, Pratap R. Angew. Chem. Int. Ed. 2011; 50: 11 400
  • 78 Čerňa I, Pohl R, Klepetářová B, Hocek M. J. Org. Chem. 2008; 73: 9048
  • 79 Vaňková B, Krchňák V, Soural M, Hlaváč J. ACS Comb. Sci. 2011; 13: 496
  • 80 Storr TE, Firth AG, Wilson K, Darley K, Baumann CG, Fairlamb IJS. Tetrahedron 2008; 64: 6125
  • 81 Baumann CG, De Ornellas S, Reeds JP, Storr TE, Williams TJ, Fairlamb IJS. Tetrahedron 2014; 70: 6174
  • 82 Reay AJ, Fairlamb IJS. Chem. Commun. (Cambridge) 2015; 51: 16 289
  • 83 Storr TE, Baumann CG, Thatcher RJ, De Ornellas S, Whitwood AC, Fairlamb IJS. J. Org. Chem. 2009; 74: 5810
  • 84 Sahnoun S, Messaoudi S, Brion J.-D, Alami M. Org. Biomol. Chem. 2009; 7: 4271
  • 85 Ngassa FN, DeKorver KA, Melistas TS, Yeh EA.-H, Lakshman MK. Org. Lett. 2006; 8: 4613
  • 86 Čerňa I, Pohl R, Hocek M. Chem. Commun. (Cambridge) 2007; 4729
  • 87 Agrofoglio LA, Gillaizeau I, Saito Y. Chem. Rev. 2003; 103: 1875
  • 88 Western EC, Shaughnessy KH. J. Org. Chem. 2005; 70: 6378
  • 89 Gigante A, Priego E.-M, Sánchez-Carrasco P, Ruiz-Pérez LM, Vande Voorde J, Camarasa M.-J, Balzarini J, González-Pacanowska D, Pérez-Pérez M.-J. Eur. J. Med. Chem. 2014; 82: 459
  • 90 Storr TE, Strohmeier JA, Baumann CG, Fairlamb IJS. Chem. Commun. (Cambridge) 2010; 46: 6470
  • 91 Huang H.-J, Lee W.-C, Yap GPA, Ong T.-G. J. Organomet. Chem. 2014; 761: 64
  • 92 Xi P, Yang F, Qin S, Zhao D, Lan J, Gao G, Hu C, You J. J. Am. Chem. Soc. 2010; 132: 1822
  • 93 Stuart DR, Fagnou K. Science (Washington, D. C.) 2007; 316: 1172
  • 94 Niu H, Su L, Zhang Q, Zhang W, Fu H, Li J, Qu G, Guo H. Chin. J. Org. Chem. 2015; 35: 1156
  • 95 Qu G.-R, Xin P.-Y, Niu H.-Y, Wang D.-C, Ding R.-F, Guo H.-M. Chem. Commun. (Cambridge) 2011; 47: 11 140
  • 96 Čerňa I, Pohl R, Klepetářová B, Hocek M. J. Org. Chem. 2010; 75: 2302
  • 97 Campeau L.-C, Parisien M, Jean A, Fagnou K. J. Am. Chem. Soc. 2006; 128: 581
  • 98 Allu S, Kumara Swamy KC. Adv. Synth. Catal. 2015; 357: 2665
  • 99 Iaroshenko VO, Ostrovskyi D, Miliutina M, Maalik A, Villinger A, Tolmachev A, Volochnyuk DM, Langer P. Adv. Synth. Catal. 2012; 354: 2495
  • 100 Meng G, Niu H.-Y, Qu G.-R, Fossey JS, Li J.-P, Guo H.-M. Chem. Commun. (Cambridge) 2012; 48: 9601
  • 101 Barbero N, SanMartin R, Domínguez E. Org. Biomol. Chem. 2010; 8: 841
  • 102 Loup J, Müller V, Ghorai D, Ackermann L. Angew. Chem. Int. Ed. 2019; 58: 1749
  • 103 Wang Y.-X, Qi S.-L, Luan Y.-X, Han X.-W, Wang S, Chen H, Ye M. J. Am. Chem. Soc. 2018; 140: 5360
  • 104 Singh MK, Akula HK, Satishkumar S, Stahl L, Lakshman MK. ACS Catal. 2016; 6: 1921
  • 105 Fumagalli F, Warratz S, Zhang S.-K, Rogge T, Zhu C, Stückl AC, Ackermann L. Chem.–Eur. J. 2018; 24: 3984
  • 106 Guo H.-M, Jiang L.-L, Niu H.-Y, Rao W.-H, Liang L, Mao R.-Z, Li D.-Y, Qu G.-R. Org. Lett. 2011; 13: 2008
  • 107 Xu C, Zhang L, Xu J, Pan Y, Li F, Li H, Xu L. ChemistrySelect 2016; 1: 653
  • 108 Vorobyeva DV, Vinogradov MM, Nelyubina YV, Loginov DA, Peregudov AS, Osipov SN. Org. Biomol. Chem. 2018; 16: 2966
  • 109 Allu S, Ravi M, Kumara Swamy KC. Eur. J. Org. Chem. 2016; 5697
  • 110 Murakami N, Yoshida M, Yoshino T, Matsunaga S. Chem. Pharm. Bull. 2018; 66: 51
  • 111 Chamala RR, Parrish D, Pradhan P, Lakshman MK. J. Org. Chem. 2013; 78: 7423
  • 112 Guo H.-M, Rao W.-H, Niu H.-Y, Jiang L.-L, Meng G, Jin J.-J, Yang X.-N, Qu G.-R. Chem. Commun. (Cambridge) 2011; 47: 5608
  • 113 Pawar AB, Lade DM. Org. Biomol. Chem. 2016; 14: 3275
  • 114 Kim JY, Park SH, Ryu J, Cho SH, Kim SH, Chang S. J. Am. Chem. Soc. 2012; 134: 9110
  • 115 Kim HJ, Ajitha MJ, Lee Y, Ryu J, Kim J, Lee Y, Jung Y, Chang S. J. Am. Chem. Soc. 2014; 136: 1132
  • 116 Pawar AB, Chang S. Org. Lett. 2015; 17: 660
  • 117 Patel P, Chang S. ACS Catal. 2015; 5: 853
  • 118 Liang Y, Liang Y.-F, Tang C, Yuan Y, Jiao N. Chem.–Eur. J. 2015; 21: 16 395
  • 119 Ali MA, Yao X, Sun H, Lu H. Org. Lett. 2015; 17: 1513
  • 120 Gou Q, Li W, Zhao Q, Xie J, Luo P, Cao G, Chen S, Qin J. Eur. J. Org. Chem. 2018; 4089
  • 121 Yoshida M, Kawai K, Tanaka R, Yoshino T, Matsunaga S. Chem. Commun. (Cambridge) 2017; 53: 5974
  • 122 Barlow HL, Teskey CJ, Greaney MF. Org. Lett. 2017; 19: 6662
  • 123 Warratz S, Burns DJ, Zhu C, Korvorapun K, Rogge T, Scholz J, Jooss C, Gelman D, Ackermann L. Angew. Chem. Int. Ed. 2017; 56: 1557
  • 124 Ruan Z, Zhang S.-K, Zhu C, Ruth PN, Stalke D, Ackermann L. Angew. Chem. Int. Ed. 2017; 56: 2045
  • 125 Qu G.-R, Liang L, Niu H.-Y, Rao W.-H, Guo H.-M, Fossey JS. Org. Lett. 2012; 14: 4494
  • 126 Li R.-L, Liang L, Xie M.-S, Qu G.-R, Niu H.-Y, Guo H.-M. J. Org. Chem. 2014; 79: 3665
  • 127 Ruan Z, Ghorai D, Zanoni G, Ackermann L. Chem. Commun. (Cambridge) 2017; 53: 9113
  • 128 Ruan Z, Lackner S, Ackermann L. ACS Catal. 2016; 6: 4690
  • 129 Allu S, Kumara Swamy KC. RSC Adv. 2015; 5: 92 045
  • 130 Banan A, Valizadeh H, Heydari A, Moghimi A. Synlett 2017; 28: 2315
  • 131 Kalimuthu P, Leimkühler S, Bernhardt PV. J. Phys. Chem. B 2012; 116: 11 600
  • 132 Coxon CR, Anscombe E, Harnor SJ, Martin MP, Carbain B, Golding BT, Hardcastle IR, Harlow LK, Korolchuk S, Matheson CJ, Newell DR, Noble MEM, Sivaprakasam M, Tudhope SJ, Turner DM, Wang LZ, Wedge SR, Wong C, Griffin RJ, Endicott JA, Cano C. J. Med. Chem. 2017; 60: 1746
  • 133 Xia R, Sun L.-P, Qu G.-R. Phosphorus, Sulfur Silicon Relat. Elem. 2017; 192: 88
  • 134 Francom P, Janeba Z, Shibuya S, Robins MJ. J. Org. Chem. 2002; 67: 6788
  • 135 Unciti-Broceta A, Pineda de las Infantas MJ, Gallo MA, Espinosa A. Chem.–Eur. J. 2007; 13: 1754
  • 136 Chattopadhyaya JB, Reese CB. Synthesis 1978; 908
  • 137 Česnek M, Masojídková M, Holý A, Šolínová V, Koval D, Kašička V. Collect. Czech. Chem. Commun. 2006; 71: 1303
  • 138 Xia R, Xie M.-S, Niu H.-Y, Qu G.-R, Guo H.-M. Green Chem. 2014; 16: 1077
  • 139 Palazzolo A, Feuillastre S, Pfeifer V, Garcia-Argote S, Bouzouita D, Tricard S, Chollet C, Marcon E, Buisson D.-A, Cholet S, Fenaille F, Lippens G, Chaudret B, Pieters G. Angew. Chem. Int. Ed. 2019; 58: 4891
  • 140 Esaki H, Aoki F, Maegawa T, Hirota K, Sajiki H. Heterocycles 2005; 66: 361
  • 141 Atzrodt J, Derdau V, Fey T, Zimmermann J. Angew. Chem. Int. Ed. 2007; 46: 7744
  • 142 Lockley WJS, McEwen A, Cooke R. J. Labelled Compd. Radiopharm. 2012; 55: 235
  • 143 Chang W, Bao D, Chun B.-K, Naduthambi D, Nagarathnam D, Rachakonda S, Reddy PG, Ross BS, Zhang H.-R, Bansal S, Espiritu CL, Keilman M, Lam AM, Niu C, Steuer HM, Furman PA, Otto MJ, Sofia MJ. ACS Med. Chem. Lett. 2011; 2: 130
  • 144 Yamauchi T, Uzui K, Nishi R, Tasaki T, Ueda T. Anticancer Res. 2014; 34: 4885
  • 145 Klotz K.-N, Falgner N, Kachler S, Lambertucci C, Vittori S, Volpini R, Cristalli G. Eur. J. Pharmacol. 2007; 556: 14
  • 146 Vongsutilers V, Daft JR, Shaughnessy KH, Gannett PM. Molecules 2009; 14: 3339
  • 147 Firth AG, Fairlamb IJS, Darley K, Baumann CG. Tetrahedron Lett. 2006; 47: 3529
  • 148 Arsenyan P, Ikaunieks M, Belyakov S. Tetrahedron Lett. 2007; 48: 961
  • 149 Liu J, Robins MJ. Org. Lett. 2005; 7: 1149
  • 150 Butora G, Schmitt C, Levorse DA, Streckfuss E, Doss GA, MacCoss M. Tetrahedron 2007; 63: 3782
  • 151 Ghosh AK, Lagisetty P, Zajc B. J. Org. Chem. 2007; 72: 8222
  • 152 Barrio JR, Namavari M, Phelps ME, Satyamurthy N. J. Am. Chem. Soc. 1996; 118: 10 408
  • 153 Kobayashi Y, Kumadaki I, Ohsawa A, Murakami S.-I. J. Chem. Soc., Chem. Commun. 1976; 430
  • 154 Sono M, Toyoda N, Shizuri Y, Tori M. Tetrahedron Lett. 1994; 35: 9237
  • 155 Lambertucci C, Antonini I, Buccioni M, Dal Ben D, Kachare DD, Volpini R, Klotz K.-N, Cristalli G. Bioorg. Med. Chem. 2009; 17: 2812
  • 156 Minetti P, Tinti MO, Carminati P, Castorina M, Di Cesare MA, Di Serio S, Gallo G, Ghirardi O, Giorgi F, Giorgi L, Piersanti G, Bartoccini F, Tarzia G. J. Med. Chem. 2005; 48: 6887
  • 157 Bliman D, Pettersson M, Bood M, Grøtli M. Tetrahedron Lett. 2014; 55: 2929
  • 158 Rayala R, Wnuk SF. Tetrahedron Lett. 2012; 53: 3333
  • 159 Maity J, Stromberg R. Molecules 2013; 18: 12 740
  • 160 Deghati PYF, Wanner MJ, Koomen G.-J. Tetrahedron Lett. 2000; 41: 1291
  • 161 Evans PA, Longmire JM. Tetrahedron Lett. 1994; 35: 8345
  • 162 Rodenko B, Koch M, van der Burg AM, Wanner MJ, Koomen G.-J. J. Am. Chem. Soc. 2005; 127: 5957
  • 163 Bookser BC, Weinhouse MI, Burns AC, Valiere AN, Valdez LJ, Stanczak P, Na J, Rheingold AL, Moore CE, Dyck B. J. Org. Chem. 2018; 83: 6334
  • 164 Robins MJ, Zou R, Guo Z, Wnuk SF. J. Org. Chem. 1996; 61: 9207
  • 165 Prajapati RK, Kumar J, Verma S. Chem. Commun. (Cambridge) 2010; 46: 3312
  • 166 García-Rubiño ME, Núñez-Carretero MC, Choquesillo-Lazarte D, García-Ruiz JM, Madrid Y, Campos JM. RSC Adv. 2014; 4: 22 425
  • 167 Chen S, Graceffa RF, Boezio AA. Org. Lett. 2016; 18: 16
  • 168 Li J.-P, Huang Y, Xie M.-S, Qu G.-R, Niu H.-Y, Wang H.-X, Qin B.-W, Guo H.-M. J. Org. Chem. 2013; 78: 12 629
  • 169 Huang R, Xie C, Huang L, Liu J. Tetrahedron 2013; 69: 577
  • 170 Aruri H, Singh U, Sharma S, Gudup S, Bhogal M, Kumar S, Singh D, Gupta VK, Kant R, Vishwakarma RA, Singh PP. J. Org. Chem. 2015; 80: 1929
  • 171 Luo Z, Jiang Z, Jiang W, Lin D. J. Org. Chem. 2018; 83: 3710
  • 172 Guo H.-M, Xia C, Niu H.-Y, Zhang X.-T, Kong S.-N, Wang D.-C, Qu G.-R. Adv. Synth. Catal. 2011; 353: 53
  • 173 Zhang Q, Cheng G, Huang Y.-Z, Qu G.-R, Niu H.-Y, Guo H.-M. Tetrahedron 2012; 68: 7822
  • 174 Xia R, Sun L.-P. Nucleosides, Nucleotides Nucleic Acids 2016; 35: 76
  • 175 Soltani Rad MN, Soleimani F. Tetrahedron 2016; 72: 4947
  • 176 Rad MNS, Behrouz S, Zarenezhad E, Kaviani N. J. Iran. Chem. Soc. 2015; 12: 1603
  • 177 Jarrige L, Levitre G, Masson G. J. Org. Chem. 2016; 81: 7230
  • 178 Zhang Q, Sun J, Zhu Y, Zhang F, Yu B. Angew. Chem. Int. Ed. 2011; 50: 4933
  • 179 Bauta WE, Schulmeier BE, Burke B, Puente JF, Cantrell Jr WR, Lovett D, Goebel J, Anderson B, Ionescu D, Guo R. Org. Process Res. Dev. 2004; 8: 889
  • 180 Vorbrueggen H. Acc. Chem. Res. 1995; 28: 509
  • 181 Bookser BC, Raffaele NB. J. Org. Chem. 2007; 72: 173
  • 182 Zhong M, Nowak I, Robins MJ. Org. Lett. 2005; 7: 4601
  • 183 Liu G.-j, Zhang X.-t, Xing G.-w. Chem. Commun. (Cambridge) 2015; 51: 12 803
  • 184 Boryski J. Nucleosides, Nucleotides Nucleic Acids 1996; 15: 771
  • 185 Sugimura H, Nitta D. Tetrahedron Lett. 2012; 53: 4460
  • 186 Krenitsky TA, Koszalka GW, Tuttle JV. Biochemistry 1981; 20: 3615
  • 187 Barai VN, Zinchenko AI, Eroshevskaya LA, Kalinichenko EN, Kulak TI, Mikhailopulo IA. Helv. Chim. Acta 2002; 85: 1901
  • 188 Liu J, Robins MJ. J. Am. Chem. Soc. 2007; 129: 5962
  • 189 Francom P, Robins MJ. J. Org. Chem. 2003; 68: 666
  • 190 Schlosser M, Cottet F. Eur. J. Org. Chem. 2002; 4181
  • 191 Liu J, Janeba Z, Robins MJ. Org. Lett. 2004; 6: 2917
  • 192 Elion GB, Hitchings GH. J. Am. Chem. Soc. 1956; 78: 3508
  • 193 Whitfield HJ, Griffin RJ, Hardcastle IR, Henderson A, Meneyrol J, Mesguiche V, Sayle KL, Golding BT. Chem. Commun. (Cambridge) 2003; 2802
  • 194 Robins MJ, Uznański B. Can. J. Chem. 1981; 59: 2601
  • 195 Zeng Q, Huang B, Danielsen K, Shukla R, Nagy T. Org. Process Res. Dev. 2004; 8: 962
  • 196 Véliz EA, Beal PA. Tetrahedron Lett. 2000; 41: 1695
  • 197 Ham YJ, Lee D.-H, Choi HG, Hah J.-M, Sim T. Tetrahedron Lett. 2010; 51: 4609
  • 198 Robins RK. J. Am. Chem. Soc. 1960; 82: 2654
  • 199 Secrist III JA, Bennett Jr LL, Allan PW, Rose LM, Chang C.-H, Montgomery JA. J. Med. Chem. 1986; 29: 2069
  • 200 Janeba Z, Francom P, Robins MJ. J. Org. Chem. 2003; 68: 989
  • 201 Brændvang M, Gundersen L.-L. Synthesis 2006; 2993
  • 202 Marchand P, Lorilleux C, Gilbert G, Gourand F, Sobrio F, Peyronnet D, Dhilly M, Barré L. ACS Med. Chem. Lett. 2010; 1: 240
  • 203 Ciuffreda P, Casati S, Santaniello E. Tetrahedron 2000; 56: 3239
  • 204 Ribard C, Rochet M, Labedan B, Daignan-Fornier B, Alzari P, Scazzocchio C, Oestreicher N. J. Mol. Biol. 2003; 334: 1117
  • 205 Liaw S.-H, Chang Y.-J, Lai C.-T, Chang H.-C, Chang G.-G. J. Biol. Chem. 2004; 279: 35 479
  • 206 Médici R, Lewkowicz ES, Iribarren AM. FEMS Microbiol. Lett. 2008; 289: 20
  • 207 Huang L.-K, Cherng Y.-C, Cheng Y.-R, Jang J.-P, Chao Y.-L, Cherng Y.-J. Tetrahedron 2007; 63: 5323
  • 208 Karran P, Attard N. Nat. Rev. Cancer 2008; 8: 24
  • 209 Aleksandrova EV. Pharm. Chem. J. (Engl. Transl.) 2003; 37: 645
  • 210 Véliz EA, Beal PA. J. Org. Chem. 2001; 66: 8592
  • 211 Maryška M, Chudíková N, Kotek V, Dvořák D, Tobrman T. Monatsh. Chem. 2013; 144: 501
  • 212 Lin X, Robins MJ. Org. Lett. 2000; 2: 3497
  • 213 Xu W, Abboud KA, Ghiviriga I, Dolbier WR, Rapp M, Wnuk SF. Org. Lett. 2006; 8: 5549
  • 214 Lakshman MK, Keeler JC, Hilmer JH, Martin JQ. J. Am. Chem. Soc. 1999; 121: 6090
  • 215 Brown GB, Weliky VS. J. Org. Chem. 1958; 23: 125
  • 216 Lakshman MK, Gunda P. Org. Lett. 2003; 5: 39
  • 217 Lakshman MK. Curr. Org. Synth. 2005; 2: 83
  • 218 Takamura-Enya T, Enomoto S, Wakabayashi K. J. Org. Chem. 2006; 71: 5599
  • 219 Thomson PF, Lagisetty P, Balzarini J, De Clercq E, Lakshman MK. Adv. Synth. Catal. 2010; 352: 1728
  • 220 Chevot F, Vabre R, Piguel S, Legraverend M. Eur. J. Org. Chem. 2012; 2889
  • 221 Dvořák L, Popa I, Štarha P, Trávníček Z. Eur. J. Org. Chem. 2010; 3441
  • 222 Ciszewski L, Waykole L, Prashad M, Repić O. Org. Process Res. Dev. 2006; 10: 799
  • 223 Wan Z.-K, Binnun E, Wilson DP, Lee J. Org. Lett. 2005; 7: 5877
  • 224 Ghodke PP, Pradeepkumar PI, In: Palladium-Catalyzed Modification of Nucleosides, Nucleotides and Oligonucleotides Kapdi AR, Maiti D, Sanghvi YS. Elsevier Amsterdam 2018; 295
  • 225 Bonala RR, Shishkina IG, Johnson F. Tetrahedron Lett. 2000; 41: 7281
  • 226 Chakraborti D, Colis L, Schneider R, Basu AK. Org. Lett. 2003; 5: 2861
  • 227 Lakshman MK, Ngassa FN, Bae S, Buchanan DG, Hahn H.-G, Mah H. J. Org. Chem. 2003; 68: 6020
  • 228 Pottabathini N, Bae S, Pradhan P, Hahn H.-G, Mah H, Lakshman MK. J. Org. Chem. 2005; 70: 7188
  • 229 Wang Z, Rizzo CJ. Org. Lett. 2001; 3: 565
  • 230 De Riccardis F, Bonala RR, Johnson F. J. Am. Chem. Soc. 1999; 121: 10 453
  • 231 Takamura-Enya T, Ishikawa S, Mochizuki M, Wakabayashi K. Tetrahedron Lett. 2003; 44: 5969
  • 232 Johnson Jr JA, Thomas HJ, Schaeffer HJ. J. Am. Chem. Soc. 1958; 80: 699
  • 233 Kotra LP, Manouilov KK, Cretton-Scott E, Sommadossi JP, Boudinot FD, Schinazi RF, Chu CK. J. Med. Chem. 1996; 39: 5202
  • 234 Adamiak RW, Biała E, Skalski B. Angew. Chem. Int. Ed. Engl. 1985; 24: 1054
  • 235 Higashiya S, Kaibara C, Fukuoka K, Suda F, Ishikawa M, Yoshida M, Hata T. Bioorg. Med. Chem. Lett. 1996; 6: 39
  • 236 Wada T, Mochizuki A, Higashiya S, Tsuruoka H, Kawahara S.-i, Ishikawa M, Sekine M. Tetrahedron Lett. 2001; 42: 9215
  • 237 Lioux T, Gosselin G, Mathé C. Eur. J. Org. Chem. 2003; 3997
  • 238 Lakshman MK, Kumar A, Balachandran R, Day BW, Andrei G, Snoeck R, Balzarini J. J. Org. Chem. 2012; 77: 5870
  • 239 Zayas J, Annoual M, Das JK, Felty Q, Gonzalez WG, Miksovska J, Sharifai N, Chiba A, Wnuk SF. Bioconjugate Chem. 2015; 26: 1519
  • 240 Cīrule D, Ozols K, Platnieks O, Bizdēna Ē, Māliņa I, Turks M. Tetrahedron 2016; 72: 4177
  • 241 Ozols K, Cīrule D, Novosjolova I, Stepanovs D, Liepinsh E, Bizdēna Ē, Turks M. Tetrahedron Lett. 2016; 57: 1174
  • 242 Butler RN. Adv. Heterocycl. Chem. 1977; 21: 323
  • 243 Temple Jr C, Kussner CL, Montgomery JA. J. Org. Chem. 1966; 31: 2210
  • 244 Temple Jr C, Thorpe MC, Coburn Jr WC, Montgomery JA. J. Org. Chem. 1966; 31: 935
  • 245 Fàbrega C, García RG, Díaz AR, Eritja R. Biol. Chem. 1998; 379: 527
  • 246 Sylvers LA, Wower J. Bioconjugate Chem. 1993; 4: 411
  • 247 Zhen Q, Xu Y.-Z, Swann PF. Nucleosides, Nucleotides Nucleic Acids 1995; 14: 939
  • 248 Holmes RE, Robins RK. J. Am. Chem. Soc. 1965; 87: 1772
  • 249 Zhu W, Ma D. Chem. Commun. (Cambridge) 2004; 888
  • 250 Feldman AK, Colasson B, Fokin VV. Org. Lett. 2004; 6: 3897
  • 251 Cosyn L, Palaniappan KK, Kim S.-K, Duong HT, Gao Z.-G, Jacobson KA, Van Calenbergh S. J. Med. Chem. 2006; 49: 7373
  • 252 Bae S, Lakshman MK. J. Am. Chem. Soc. 2009; 131: 17 993
  • 253 Lakshman MK, Singh MK, Parrish D, Balachandran R, Day BW. J. Org. Chem. 2010; 75: 2461
  • 254 Frieden M, Aviñó A, Eritja R. Nucleosides, Nucleotides Nucleic Acids 2003; 22: 193
  • 255 Hein CD, Liu X.-M, Wang D. Pharm. Res. 2008; 25: 2216
  • 256 Weber L. Drug Discovery Today: Technol. 2004; 1: 261
  • 257 Kolb HC, Sharpless KB. Drug Discovery Today 2003; 8: 1128
  • 258 Meghani NM, Amin HH, Lee B.-J. Drug Discovery Today 2017; 22: 1604
  • 259 Lin P.-C, Ueng S.-H, Yu S.-C, Jan M.-D, Adak AK, Yu C.-C, Lin C.-C. Org. Lett. 2007; 9: 2131
  • 260 White MA, Johnson JA, Koberstein JT, Turro NJ. J. Am. Chem. Soc. 2006; 128: 11 356
  • 261 Baskin JM, Prescher JA, Laughlin ST, Agard NJ, Chang PV, Miller IA, Lo A, Codelli JA, Bertozzi CR. Proc. Natl. Acad. Sci. U. S. A. 2007; 104: 16 793
  • 262 Laughlin ST, Bertozzi CR. ACS Chem. Biol. 2009; 4: 1068
  • 263 Belardi B, de la Zerda A, Spiciarich DR, Maund SL, Peehl DM, Bertozzi CR. Angew. Chem. Int. Ed. 2013; 52: 14 045
  • 264 Kovaļovs A, Novosjolova I, Bizdēna Ē, Bižāne I, Skardziute L, Kazlauskas K, Jursenas S, Turks M. Tetrahedron Lett. 2013; 54: 850
  • 265 Amblard F, Cho JH, Schinazi RF. Chem. Rev. 2009; 109: 4207
  • 266 Kavoosi S, Rayala R, Walsh B, Barrios M, Gonzalez WG, Miksovska J, Mathivathanan L, Raptis RG, Wnuk SF. Tetrahedron Lett. 2016; 57: 4364
  • 267 Qu G.-R, Mao Z.-J, Niu H.-Y, Wang D.-C, Xia C, Guo H.-M. Org. Lett. 2009; 11: 1745
  • 268 Guo H.-M, Zhang Y, Niu H.-Y, Wang D.-C, Chu Z.-L, Qu G.-R. Org. Biomol. Chem. 2011; 9: 2065
  • 269 Ohno M, Gao Z.-G, Van Rompaey P, Tchilibon S, Kim S.-K, Harris BA, Gross AS, Duong HT, Van Calenbergh S, Jacobson KA. Bioorg. Med. Chem. 2004; 12: 2995
  • 270 Šála M, De Palma AM, Hřebabecký H, Dejmek M, Dračínský M, Leyssen P, Neyts J, Mertlíková-Kaiserová H, Nencka R. Bioorg. Med. Chem. Lett. 2011; 21: 4271
  • 271 Cai J, Bennett DJ, Rankovic Z, Dempster M, Fradera X, Gillespie J, Cumming I, Finlay W, Baugh M, Boucharens S, Bruin J, Cameron KS, Hamilton W, Kerr J, Kinghorn E, McGarry G, Robinson J, Scullion P, Uitdehaag JCM, van Zeeland M, Potin D, Saniere L, Fouquet A, Chevallier F, Deronzier H, Dorleans C, Nicolai E. Bioorg. Med. Chem. Lett. 2010; 20: 4447
  • 272 Bartoccini F, Piersanti G, Armaroli S, Cerri A, Cabri W. Tetrahedron Lett. 2014; 55: 1376
  • 273 Fürstner A, Leitner A, Méndez M, Krause H. J. Am. Chem. Soc. 2002; 124: 13 856
  • 274 Beckman J, Kincaid K, Hocek M, Spratt T, Engels J, Cosstick R, Kuchta RD. Biochemistry 2007; 46: 448
  • 275 Hocek M, Dvořáková H. J. Org. Chem. 2003; 68: 5773
  • 276 Hocek M, Hocková D, Dvořáková H. Synthesis 2004; 889
  • 277 Hocek M, Šilhár P, Pohl R. Collect. Czech. Chem. Commun. 2006; 71: 1484
  • 278 Hocek M, Pohl R, Císařová I. Eur. J. Org. Chem. 2005; 3026
  • 279 Hocek M, Šilhár P, Shih I.-h, Mabery E, Mackman R. Bioorg. Med. Chem. Lett. 2006; 16: 5290
  • 280 Kim B.-T, Moon WS, Lee J.-H, Hwang K.-J. Bull. Korean Chem. Soc. 2007; 28: 915
  • 281 Sedláček O, Břehová P, Pohl R, Holý A, Janeba Z. Can. J. Chem. 2011; 89: 488
  • 282 Litinas KE, Thalassitis A. Tetrahedron Lett. 2010; 51: 6451
  • 283 Hirota K, Kitade Y, Kanbe Y, Maki Y. J. Org. Chem. 1992; 57: 5268
  • 284 Gannett PM, Heavner S, Daft JR, Shaughnessy KH, Epperson JD, Greenbaum NL. Chem. Res. Toxicol. 2003; 16: 1385
  • 285 Kohyama N, Katashima T, Yamamoto Y. Synthesis 2004; 2799
  • 286 Gubala V, Betancourt JE, Rivera JM. Org. Lett. 2004; 6: 4735
  • 287 Western EC, Daft JR, Johnson EM, Gannett PM, Shaughnessy KH. J. Org. Chem. 2003; 68: 6767
  • 288 Hobley G, Gubala V, Del C. Rivera-Sánchez M, Rivera JM. Synlett 2008; 1510
  • 289 Collier A, Wagner GK. Synth. Commun. 2006; 36: 3713
  • 290 Zilbershtein L, Silberman A, Fischer B. Org. Biomol. Chem. 2011; 9: 7763
  • 291 Weishar JL, McLaughlin CK, Baker M, Gabryelski W, Manderville RA. Org. Lett. 2008; 10: 1839
  • 292 Dai Q, Xu D, Lim K, Harvey RG. J. Org. Chem. 2007; 72: 4856
  • 293 Manderville RA, Omumi A, Rankin KM, Wilson KA, Millen AL, Wetmore SD. Chem. Res. Toxicol. 2012; 25: 1271
  • 294 Rankin KM, Sproviero M, Rankin K, Sharma P, Wetmore SD, Manderville RA. J. Org. Chem. 2012; 77: 10 498
  • 295 Schlitt KM, Millen AL, Wetmore SD, Manderville RA. Org. Biomol. Chem. 2011; 9: 1565
  • 296 McLaughlin CK, Lantero DR, Manderville RA. J. Phys. Chem. A 2006; 110: 6224
  • 297 Amann N, Wagenknecht H.-A. Synlett 2002; 687
  • 298 Mayer E, Valis L, Huber R, Amann N, Wagenknecht H.-A. Synthesis 2003; 2335
  • 299 Gayakhe V, Ardhapure A, Kapdi AR, Sanghvi YS, Serrano JL, García L, Pérez J, García J, Sánchez G, Fischer C, Schulzke C. J. Org. Chem. 2016; 81: 2713
  • 300 Bhilare S, Gayakhe V, Ardhapure AV, Sanghvi YS, Schulzke C, Borozdina Y, Kapdi AR. RSC Adv. 2016; 6: 83 820
  • 301 Gayakhe V, Ardhapure AV, Kapdi AR, Sanghvi YS, Serrano JL, Schulzke C. Curr. Protoc. Nucleic Acid Chem. 2016; 65: 1.37.1.
  • 302 Collier A, Wagner G. Org. Biomol. Chem. 2006; 4: 4526
  • 303 Omumi A, Beach DG, Baker M, Gabryelski W, Manderville RA. J. Am. Chem. Soc. 2011; 133: 42
  • 304 Pesnot T, Kempter J, Schemies J, Pergolizzi G, Uciechowska U, Rumpf T, Sippl W, Jung M, Wagner GK. J. Med. Chem. 2011; 54: 3492
  • 305 Zhang B, Wagner GK, Weber K, Garnham C, Morgan AJ, Galione A, Guse AH, Potter BVL. J. Med. Chem. 2008; 51: 1623
  • 306 Collier A, Wagner GK. Chem. Commun. (Cambridge) 2008; 178
  • 307 Čapek P, Pohl R, Hocek M. Org. Biomol. Chem. 2006; 4: 2278
  • 308 Čapek P, Hocek M. Synlett 2005; 3005
  • 309 Vrábel M, Pohl R, Klepetářová B, Votruba I, Hocek M. Org. Biomol. Chem. 2007; 5: 2849
  • 310 Sessler JL, Sathiosatham M, Doerr K, Lynch V, Abboud KA. Angew. Chem. Int. Ed. 2000; 39: 1300
  • 311 Andrei M, Bjørnstad V, Langli G, Rømming C, Klaveness J, Taskén K, Undheim K. Org. Biomol. Chem. 2007; 5: 2070
  • 312 Dang Q, Brown BS, Liu Y, Rydzewski RM, Robinson ED, Poelje PDv, Reddy MR, Erion MD. J. Med. Chem. 2009; 52: 2880
  • 313 Lang P, Gerez C, Tritsch D, Fontecave M, Biellmann J.-F, Burger A. Tetrahedron 2003; 59: 7315
  • 314 Kaura M, Kumar P, Hrdlicka PJ. J. Org. Chem. 2014; 79: 6256
  • 315 Müllar S, Strohmeier J, Diederichsen U. Org. Lett. 2012; 14: 1382
  • 316 Sessler JL, Jayawickramarajah J, Sathiosatham M, Sherman CL, Brodbelt JS. Org. Lett. 2003; 5: 2627
  • 317 Nadler A, Strohmeier J, Diederichsen U. Angew. Chem. Int. Ed. 2011; 50: 5392
  • 318 Matsumoto K, Takahashi N, Suzuki A, Morii T, Saito Y, Saito I. Bioorg. Med. Chem. Lett. 2011; 21: 1275
  • 319 Kaucher MS, Davis JT. Tetrahedron Lett. 2006; 47: 6381
  • 320 Murata T, Miyazaki E, Maki S, Umemoto Y, Ohmoto M, Nakasuji K, Morita Y. Bull. Chem. Soc. Jpn. 2012; 85: 995
  • 321 Ogasawara S, Saito I, Maeda M. Tetrahedron Lett. 2008; 49: 2479
  • 322 Lena S, Neviani P, Masiero S, Pieraccini S, Spada GP. Angew. Chem. Int. Ed. 2010; 49: 3657
  • 323 Holzberger B, Strohmeier J, Siegmund V, Diederichsen U, Marx A. Bioorg. Med. Chem. Lett. 2012; 22: 3136
  • 324 Dumas A, Luedtke NW. Nucleic Acids Res. 2011; 39: 6825
  • 325 Blanchard DJM, Fadock KL, Sproviero M, Deore PS, Cservenyi TZ, Manderville RA, Sharma P, Wetmore SD. J. Mater. Chem. C 2016; 4: 2915
  • 326 Abou-Elkhair RAI, Dixon DW, Netzel TL. J. Org. Chem. 2009; 74: 4712
  • 327 Nandi B, Pattanayak S, Paul S, Sinha S. Eur. J. Org. Chem. 2013; 1271
  • 328 Reddy MR, Shibata N, Kondo Y, Nakamura S, Toru T. Angew. Chem. Int. Ed. 2006; 45: 8163
  • 329 Lambertucci C, Costanzi S, Vittori S, Volpini R, Cristalli G. Nucleosides, Nucleotides Nucleic Acids 2001; 20: 1153
  • 330 Dalhoff C, Hüben M, Lenz T, Poot P, Nordhoff E, Köster H, Weinhold E. ChemBioChem 2010; 11: 256
  • 331 Crisp GT, Jiang Y.-L. Tetrahedron Lett. 2002; 43: 3157
  • 332 Camacho-García J, Montoro-García C, López-Pérez AM, Bilbao N, Romero-Pérez S, González-Rodríguez D. Org. Biomol. Chem. 2015; 13: 4506
  • 333 Bilbao N, Vázquez-González V, Aranda MT, González-Rodríguez D. Eur. J. Org. Chem. 2015; 7160
  • 334 Bang E.-K, Won J, Moon D, Lee JY, Kim BH. Chem.–Asian J. 2011; 6: 2048
  • 335 Saito Y, Matsumoto K, Bag SS, Ogasawara S, Fujimoto K, Hanawa K, Saito I. Tetrahedron 2008; 64: 3578
  • 336 Shinohara Y, Matsumoto K, Kugenuma K, Morii T, Saito Y, Saito I. Bioorg. Med. Chem. Lett. 2010; 20: 2817
  • 337 Lim J, Miljanić OŠ. CrystEngComm 2011; 13: 5309
  • 338 Ali H, Ahmed N, Tessier G, van Lier JE. Bioorg. Med. Chem. Lett. 2006; 16: 317
  • 339 Coutouli-Argyropoulou E, Tsitabani M, Petrantonakis G, Terzis A, Raptopoulou C. Org. Biomol. Chem. 2003; 1: 1382
  • 340 Volpini R, Costanzi S, Lambertucci C, Vittori S, Klotz K.-N, Lorenzen A, Cristalli G. Bioorg. Med. Chem. Lett. 2001; 11: 1931
  • 341 Volpini R, Costanzi S, Lambertucci C, Vittori S, Martini C, Trincavelli ML, Klotz K.-N, Cristalli G. Purinergic Signalling 2005; 1: 173
  • 342 Scheidt HA, Flasche W, Cismas C, Rost M, Herrmann A, Liebscher J, Huster D. J. Phys. Chem. B 2004; 108: 16 279
  • 343 Flasche W, Cismas C, Herrmann A, Liebscher J. Synthesis 2004; 2335
  • 344 Olejniczak A, Wojtczak B, Lesnikowski ZJ. Nucleosides, Nucleotides Nucleic Acids 2007; 26: 1611
  • 345 Bednarska K, Olejniczak AB, Wojtczak BA, Sułowska Z, Leśnikowski ZJ. ChemMedChem 2010; 5: 749
  • 346 O’Mahony G, Ehrman E, Grøtli M. Tetrahedron 2008; 64: 7151
  • 347 Nim-anussornkul D, Vilaivan T. Bioorg. Med. Chem. 2017; 25: 6388
  • 348 Okamoto A, Ochi Y, Saito I. Chem. Commun. (Cambridge) 2005; 1128
  • 349 Saito Y, Hanawa K, Motegi K, Omoto K, Okamoto A, Saito I. Tetrahedron Lett. 2005; 46: 7605
  • 350 Saito Y, Suzuki A, Imai K, Nemoto N, Saito I. Tetrahedron Lett. 2010; 51: 2606
  • 351 Seo YJ, Ryu JH, Kim BH. Org. Lett. 2005; 7: 4931
  • 352 Aso T, Saito K, Suzuki A, Saito Y. Org. Biomol. Chem. 2015; 13: 10 540
  • 353 Kaura M, Hrdlicka PJ. Org. Biomol. Chem. 2015; 13: 7236
  • 354 Zhang X, Bernet B, Vasella A. Helv. Chim. Acta 2006; 89: 2861
  • 355 Dierckx A, Dinér P, El-Sagheer AH, Kumar JD, Brown T, Grøtli M, Wilhelmsson LM. Nucleic Acids Res. 2011; 39: 4513
  • 356 Ishizuka T, Zhao P.-Y, Bao H.-L, Xu Y. Analyst 2017; 142: 4083
  • 357 Redwan IN, Bliman D, Tokugawa M, Lawson C, Grøtli M. Tetrahedron 2013; 69: 8857
  • 358 Zhang W, Gao Q, Wei S, Fu B, Yang Q, Ming X. Chem. Biodiversity 2018; 15: e1 700 335
  • 359 Firth AG, Wilson K, Baumann CG, Fairlamb IJS. Nucleosides, Nucleotides Nucleic Acids 2011; 30: 168
  • 360 Garg NK, Woodroofe CC, Lacenere CJ, Quake SR, Stoltz BM. Chem. Commun. (Cambridge) 2005; 4551
  • 361 Tierney MT, Grinstaff MW. Org. Lett. 2000; 2: 3413
  • 362 Čapek P, Cahová H, Pohl R, Hocek M, Gloeckner C, Marx A. Chem.–Eur. J. 2007; 13: 6196
  • 363 Cho JH, Prickett CD, Shaughnessy KH. Eur. J. Org. Chem. 2010; 3678
  • 364 Panda B, Sarkar TK. Chem. Commun. (Cambridge) 2010; 46: 3131
  • 365 Brændvang M, Gundersen L.-L. Bioorg. Med. Chem. 2007; 15: 7144
  • 366 Wang Y, Shakespeare WC, Huang W.-S, Sundaramoorthi R, Lentini S, Das S, Liu S, Banda G, Wen D, Zhu X, Xu Q, Keats J, Wang F, Wardwell S, Ning Y, Snodgrass JT, Broudy MI, Russian K, Dalgarno D, Clackson T, Sawyer TK. Bioorg. Med. Chem. Lett. 2008; 18: 4907
  • 367 Bartoccini F, Cabri W, Celona D, Minetti P, Piersanti G, Tarzia G. J. Org. Chem. 2010; 75: 5398
  • 368 Gurram V, Pottabathini N, Garlapati R, Chaudhary AB, Patro B, Lakshman MK. Chem.–Asian J. 2012; 7: 1853
  • 369 Wan Z, Boehm JC, Bower MJ, Kassis S, Lee JC, Zhao B, Adams JL. Bioorg. Med. Chem. Lett. 2003; 13: 1191
  • 370 Vandromme L, Piguel S, Lozach O, Meijer L, Legraverend M, Grierson DS. Bioorg. Med. Chem. Lett. 2006; 16: 3144
  • 371 Lakshman MK, Hilmer JH, Martin JQ, Keeler JC, Dinh YQV, Ngassa FN, Russon LM. J. Am. Chem. Soc. 2001; 123: 7779
  • 372 Čapek P, Vrábel M, Hasník Z, Pohl R, Hocek M. Synthesis 2006; 3515
  • 373 Venkatesan AM, Dehnhardt CM, Chen Z, Santos ED, Dos Santos O, Bursavich M, Gilbert AM, Ellingboe JW, Ayral-Kaloustian S, Khafizova G, Brooijmans N, Mallon R, Hollander I, Feldberg L, Lucas J, Yu K, Gibbons J, Abraham R, Mansour TS. Bioorg. Med. Chem. Lett. 2010; 20: 653
  • 374 Chiosis G, Lucas B, Shtil A, Huezo H, Rosen N. Bioorg. Med. Chem. 2002; 10: 3555
  • 375 Nair V, Ma X, Shu Q, Zhang F, Uchil V, Cherukupalli GR. Nucleosides, Nucleotides Nucleic Acids 2007; 26: 651
  • 376 Zulfiqar F, Kojima H, Nakanishi M, Ando T, Kitade Y. Nucleosides, Nucleotides Nucleic Acids 2008; 27: 1153
  • 377 Wicke L, Engels JW. Bioconjugate Chem. 2012; 23: 627
  • 378 Kim HO. Arch. Pharmacal Res. 2001; 24: 508
  • 379 van Tilburg EW, Gremmen M, von Frijtag Drabbe Künzel J, de Groote M, Ijzerman AP. Bioorg. Med. Chem. 2003; 11: 2183
  • 380 Rieger JM, Brown ML, Sullivan GW, Linden J, Macdonald TL. J. Med. Chem. 2001; 44: 531
  • 381 Brun V, Legraverend M, Grierson DS. Tetrahedron 2002; 58: 7911
  • 382 Ghatnekar J, Hägerlöf M, Oredsson S, Alm K, Elmroth SKC, Persson T. Bioorg. Med. Chem. 2007; 15: 7426
  • 383 Beattie D, Brearley A, Brown Z, Charlton SJ, Cox B, Fairhurst RA, Fozard JR, Gedeck P, Kirkham P, Meja K, Nanson L, Neef J, Oakman H, Spooner G, Taylor RJ, Turner RJ, West R, Woodward H. Bioorg. Med. Chem. Lett. 2010; 20: 1219
  • 384 Hou X, Kim HO, Alexander V, Kim K, Choi S, Park S.-g, Lee JH, Yoo LS, Gao Z.-G, Jacobson KA, Jeong LS. ACS Med. Chem. Lett. 2010; 1: 516
  • 385 Hou X, Majik MS, Kim K, Pyee Y, Lee Y, Alexander V, Chung H.-J, Lee HW, Chandra G, Lee JH, Park S.-g, Choi WJ, Kim HO, Phan K, Gao Z.-G, Jacobson KA, Choi S, Lee SK, Jeong LS. J. Med. Chem. 2012; 55: 342
  • 386 Tosh DK, Ciancetta A, Warnick E, O’Connor R, Chen Z, Gizewski E, Crane S, Gao Z.-G, Auchampach JA, Salvemini D, Jacobson KA. J. Med. Chem. 2016; 59: 3249
  • 387 Bednarska K, Olejniczak AB, Piskala A, Klink M, Sulowska Z, Lesnikowski ZJ. Bioorg. Med. Chem. 2012; 20: 6621
  • 388 Żołnierczyk JD, Olejniczak AB, Mieczkowski A, Błoński JZ, Kiliańska ZM, Robak T, Leśnikowski ZJ. Bioorg. Med. Chem. 2016; 24: 5076
  • 389 Thompson S, Fleming IN, O’Hagan D. Org. Biomol. Chem. 2016; 14: 3120
  • 390 Malthum S, Polkam N, Allaka TR, Chepuri K, Anireddy JS. Tetrahedron Lett. 2017; 58: 4166
  • 391 Volpini R, Costanzi S, Lambertucci C, Taffi S, Vittori S, Klotz K.-N, Cristalli G. J. Med. Chem. 2002; 45: 3271
  • 392 Čapek P, Pohl R, Hocek M. J. Org. Chem. 2004; 69: 7985
  • 393 Šilhár P, Pohl R, Votruba I, Hocek M. Org. Lett. 2004; 6: 3225
  • 394 Kuchař M, Pohl R, Klepetářová B, Votruba I, Hocek M. Org. Biomol. Chem. 2008; 6: 2377
  • 395 Hassan AEA, Abou-Elkhair RAI, Riordan JM, Allan PW, Parker WB, Khare R, Waud WR, Montgomery JA, Secrist III JA. Eur. J. Med. Chem. 2012; 47: 167
  • 396 Wang D.-C, Niu H.-Y, Qu G.-R, Liang L, Wei X.-J, Zhang Y, Guo H.-M. Org. Biomol. Chem. 2011; 9: 7663
  • 397 Hocek M, Holý A, Votruba I, Dvořáková H. Collect. Czech. Chem. Commun. 2001; 66: 483
  • 398 Qu G.-R, Xin P.-Y, Niu H.-Y, Jin X, Guo X.-T, Yang X.-N, Guo H.-M. Tetrahedron 2011; 67: 9099
  • 399 Donald A, McHardy T, Rowlands MG, Hunter L.-JK, Davies TG, Berdini V, Boyle RG, Aherne GW, Garrett MD, Collins I. J. Med. Chem. 2007; 50: 2289
  • 400 Hocek M, Nauš P, Pohl R, Votruba I, Furman PA, Tharnish PM, Otto MJ. J. Med. Chem. 2005; 48: 5869
  • 401 Buchanan HS, Pauff SM, Kosmidis TD, Taladriz-Sender A, Rutherford OI, Hatit MZC, Fenner S, Watson AJB, Burley GA. Org. Lett. 2017; 19: 3759
  • 402 Pratap R, Parrish D, Gunda P, Venkataraman D, Lakshman MK. J. Am. Chem. Soc. 2009; 131: 12 240
  • 403 Besada P, Costas T, Teijeira M, Terán C. Eur. J. Med. Chem. 2010; 45: 6114
  • 404 Ren H, An H, Hatala PJ, Stevens Jr WC, Tao J, He B. Beilstein J. Org. Chem. 2015; 11: 2509
  • 405 Amiable C, Paoletti J, Haouz A, Padilla A, Labesse G, Kaminski P.-A, Pochet S. Eur. J. Med. Chem. 2014; 85: 418
  • 406 Abeijón P, Blanco JM, Caamaño O, Fernández F, García MD, García-Mera X, Rodríguez-Borges JE, Balzarini J, De Clercq E. Synthesis 2009; 2766
  • 407 Lakshman MK, Thomson PF, Nuqui MA, Hilmer JH, Sevova N, Boggess B. Org. Lett. 2002; 4: 1479
  • 408 Gundersen L.-L, Nissen-Meyer J, Spilsberg B. J. Med. Chem. 2002; 45: 1383
  • 409 Fujiwara T, Kimoto M, Sugiyama H, Hirao I, Yokoyama S. Bioorg. Med. Chem. Lett. 2001; 11: 2221
  • 410 Gillespie RJ, Cliffe IA, Dawson CE, Dourish CT, Gaur S, Jordan AM, Knight AR, Lerpiniere J, Misra A, Pratt RM, Roffey J, Stratton GC, Upton R, Weiss SM, Williamson DS. Bioorg. Med. Chem. Lett. 2008; 18: 2924
  • 411 Nicolaou KC, Ellery SP, Rivas F, Saye K, Rogers E, Workinger TJ, Schallenberger M, Tawatao R, Montero A, Hessell A, Romesberg F, Carson D, Burton D. Bioorg. Med. Chem. 2011; 19: 5648
  • 412 Selig R, Schollmeyer D, Albrecht W, Laufer S. Tetrahedron 2011; 67: 9204
  • 413 Bråthe A, Andresen G, Gundersen L.-L, Malterud KE, Rise F. Bioorg. Med. Chem. 2002; 10: 1581
  • 414 Bråthe A, Gundersen L.-L, Nissen-Meyer J, Rise F, Spilsberg B. Bioorg. Med. Chem. Lett. 2003; 13: 877
  • 415 Wang J.-F, Zhang L.-R, Yang Z.-J, Zhang L.-H. Bioorg. Med. Chem. 2004; 12: 1425
  • 416 Ngassa FN, Lindsey EA, Haines BE. Tetrahedron 2009; 65: 4085
  • 417 Nauš P, Votruba I, Hocek M. Collect. Czech. Chem. Commun. 2004; 69: 1955
  • 418 Křováček M, Dvořák D. J. Heterocycl. Chem. 2015; 52: 40
  • 419 Takahashi K, Ito S, Nakamoto K, Ito Y, Ueno Y. J. Org. Chem. 2015; 80: 8561
  • 420 Chang LCW, Spanjersberg RF, von Frijtag Drabbe Künzel JK, Mulder-Krieger T, Brussee J, Ijzerman AP. J. Med. Chem. 2006; 49: 2861
  • 421 Heuberger BD, Shin D, Switzer C. Org. Lett. 2008; 10: 1091