Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

Abstract

Cyanoacetylenic alcohols, R¹R²C(OH)C≡C–CN, the closest derivatives of cyanoacetylene, an abundant interstellar molecule, are now becoming important compounds in the area of modern organic synthesis that tends to mimic Nature. The presence of highly reactive C≡C and C≡N bonds in close proximity to a hydroxy group endows cyanoacetylenic alcohols with a chemical trinity of mutually influencing functions, leading to a myriad number of chemical transformations. All reactions of cyanoacetylenic alcohols parallel modern organic synthesis, whilst being biomimetic. To react, they do not need transition metals (and in most cases, no metals at all, except for physiologically indispensable Na⁺ and K⁺), proceed at ambient temperature and often in aqueous media. Fundamentally, their reactions are 100% atom-economic because they are almost exclusively addition processes. Typically, the cyano, acetylene and hydroxy functions of cyanoacetylenic alcohols behave as an inseparable entity, leading to reaction products with multiple functional groups. This allows hydroxy, carbonyl, carboxylic, imino, amino, amido, cyanoamido, cyano, various P-containing, ether and ester functions, along with double bonds, different fundamental heterocycles (furans, furanones, pyrazoles, oxazoles, pyridines, pyrimidines, purines, etc.) and diverse polycyclic systems to be integrated in a single molecular architecture. This review focuses on an analysis and generalization of the knowledge that has accumulated on the chemistry of cyanoacetylenic alcohols, mostly over the past 15 years.

1 Introduction

2 Nucleophilic Addition to Cyanoacetylenic Alcohols and Subsequent Transformations of the Adducts

3 Annulation with Nonaromatic Nitrogen Heterocycles

4 Annulation with Aromatic Nitrogen Heterocycles

5 Modification of Amino Acids

6 Modifications of Nucleobases

7 Modification of Nucleosides

8 Conclusion

Key words

cyanoacetylenic alcohols - nucleophilic addition - annulation - modification - fundamental heterocycles

Publication History

Received: 22 March 2021

Accepted after revision: 28 April 2021

Accepted Manuscript online:
28 April 2021

Article published online:
26 May 2021

• References

• 1a Kunde VG, Aikin AC, Hanel RA, Jennings DE, Maguire WC, Samuelson RE. Nature 1981; 292: 686
• 1b Nguyen-Q-Rieu, Graham D, Bujarrabal V. Astron. Astrophys. 1984; 138: L5
• 1c Botschwina P. Chem. Phys. Lett. 1987; 139: 255
• 1d Combes F, Gerin M, Wootten A, Wlodarczak G, Clausset F, Encrenaz PJ. Astron. Astrophys. 1987; 180: L13
• 1e Amano T, Saito S, Yamamoto S, Kawaguchi K, Suzuki H, Ohishi M, Kaifu N. Astrophys. J. 1990; 351: 500
• 1f Kawaguchi K, Masatoshi K, Keiichi T, Eizi H. J. Mol. Spectrosc. 1990; 144: 451
• 1g Kawaguchi K, Takano S, Ohishi M, Ishikawa S.-I, Miyazawa K, Kaifu N, Yamashita K, Yamamoto S, Saito S, Ohshima Y, Endo Y. Astrophys. J. Lett. 1992; 396: L49
• 1h Kawaguchi K, Kasai Y, Ishikawa S.-I, Ohishi M, Kaifu N, Amano T. Astrophys. J. Lett. 1994; 420: L95
• 1i Huebner WF. Earth Moon Planets 2002; 89: 179
• 1j Borget F, Chiavassa T, Allouche A, Marinelli F, Aycard J.-P. J. Am. Chem. Soc. 2001; 123: 10668
• 1k Khanna RK. Icarus 2005; 178: 165
• 1l Trolez Y, Guillemin J.-C. Angew. Chem. Int. Ed. 2005; 44: 7224
• 1m Fuente A, García-Burillo S, Gerin M, Teyssier D, Usero A, Rizzo JR, de Vicente P. Astrophys. J. 2005; 619: L155
• 1n Horn A, Møllendal H, Guillemin J.-C. J. Phys. Chem. A 2008; 112: 11009
• 1o Couturier-Tamburelli I, Sessouma B, Chiavassa T, Piétri N. J. Phys. Chem. A 2012; 116: 10721
• 1p McGuire BA. Astrophys. J., Suppl. Ser. 2018; 239: 17
• 2a Orgel LE. Crit. Rev. Biochem. Mol. Biol. 2004; 39: 99
• 2b Benidar A, Guillemin J.-C, Mó O, Yáñez M. J. Phys. Chem. A 2005; 109: 4705
• 2c Aylward N, Bofinger NA. Biophys. Chem. 2006; 123: 113
• 2d Ziurys LM. PNAS 2006; 103: 12274
• 2e Anastasi C, Crowe MA, Sutherland JD. J. Am. Chem. Soc. 2007; 129: 24
• 2f Powner MW, Gerland B, Sutherland JD. Nature 2009; 459: 230
• 2g Ruiz-Mirazo K, Briones C, de la Escosura A. Chem. Rev. 2014; 114: 285
• 2h Patel BH, Percivalle C, Ritson DJ, Duffy CD, Sutherland JD. Nat. Chem. 2015; 7: 301
• 2i Tsanakopoulou M, Xu J, Bond AD, Sutherland JD. Chem. Commun. 2017; 53: 3327
• 3 Landor SR, Demetriou B, Grzeskowiak R, Pavey D. J. Organomet. Chem. 1975; 93: 129
• 4a Fomum ZT, Asobo RF, Landor SR, Landor PD. Chem. Commun. 1983; 23: 1455
• 4b Fomum ZT, Asobo RF, Landor SR, Landor PD. J. Chem. Soc., Perkin Trans. 1 1984; 1078
• 4c Fomum ZT, Ifeadike PN. J. Heterocycl. Chem. 1985; 22: 1611
• 4d Landor SR, Asobo PF, Fomum ZT, Roberts R. J. Chem. Soc., Perkin Trans. 1 1991; 1201
• 5 Fleming FF, Gudipati V, Steward OW. Org. Lett. 2002; 659
• 6 Fleming FF, Gudipati V, Steward OW. Tetrahedron 2003; 59: 5585
• 7a Trofimov BA, Mal’kina AG, Skvortsov YuM. Russ. J. Org. Chem. 1994; 29: 1053
• 7b Trofimov BA, Mal’kina AG. Heterocycles 1999; 51: 2485
• 8 Hopf H, Witulski B. Functionalized Acetylenes in Organic Synthesis – The Case of the 1-Cyano- and 1-Halogenoacetylenes. In Modern Acetylene Chemistry. Stang PJ, Diederich F. VCH; Weinheim: 1995: 33
• 9 Bhatt D, Kumari C, Goswami A. Asian J. Org. Chem. 2019; 8: 1985
• 10a Turner BE. Astrophys. J. 1971; 163: L35
• 10b De Zafra RL. Astrophys. J. 1971; 170: 163
• 10c Dickinson DF. Astrophys. Lett. 1972; 12: 235
• 10d Solomon PM. Phys. Today 1973; 26: 32
• 10e Osamura Y, Petrie S. J. Phys. Chem. A 2004; 108: 3615
• 10f Petrie S, Osamura Y. J. Phys. Chem. A 2004; 108: 3623
• 11a Sanchez RA, Ferris JP, Orgel LE. Science 1966; 154: 784
• 11b Ferris JP, Sanchez RA, Orgel EL. J. Mol. Biol. 1968; 33: 693
• 12a Mal’kina AG, Shemyakina OA, Nosyreva VV, Albanov AI, Klyba LV, Zhanchipova ER, Trofimov BA. Synthesis 2006; 637
• 12b Mal’kina AG, Shemyakina OA, Nosyreva VV, Albanov AI, Klyba LV, Zhanchipova ER, Trofimov BA. Mendeleev Commun. 2006; 228
• 13 Kudyakova RN, Skvortsov YuM, Mal’kina AG, Kositsyna EI, Modonov VB. Russ. J. Org. Chem. 1991; 27: 451
• 14 Skvortsov YuM, Mal’kina AG, Trofimov BA, Kalabin GA, Volkov AN, Modonov VB. Russ. Chem. Bull. 1980; 29: 967
• 15 Skvortsov YuM, Mal’kina AG, Trofimov BA. Chem. Heterocycl. Compd. 1983; 19: 806
• 16 Andriyankova LV, Abramova ND, Mal’kina AG, Skvortsov YuM. Russ. Chem. Bull. 1989; 38: 1301
• 17 Mal’kina AG, Sokolyanskaya LV, Kudyakova RN, Sinegovskaya LM, Albanov AI, Shemyakina OA, Trofimov BA. Russ. J. Org. Chem. 2005; 41: 61
• 18 Trofimov BA, Mal’kina AG, Shemyakina OA, Kudyakova RN, Sokolyanskaya LV, Sinegovskaya LM, Albanov AI, Smirnov VI, Kazheva ON, Chekhlov AN, D’yachenko OA. Russ. J. Org Chem. 2005; 41: 884
• 19 Trofimov BA, Mal’kina AG, Borisova AP, Nosyreva VV, Shemyakina OA, Kazheva ON, Shilov GV, Dyachenko OA. Tetrahedron Lett. 2008; 19: 3104
• 20 Lown JW, Ma JS. N. Can. J. Chem. 1967; 45: 953
• 21 Nakhmanovich AS, Glotova TE. Chem. Heterocycl. Compd. 1985; 21: 955
• 22 Murahashi S, Ryutani B, Shuto Y. J. Chem. Soc. Jpn., Pure Chem. Sect. 1957; 78: 324
• 23a Elguero J, Goya P, Jagerovic N, Silva AM. S. Targets Heterocycl. Syst. 2002; 6: 52
• 23b Deng X, Mani NS. Org. Lett. 2006; 8: 3505
• 23c Singh P, Paul K, Holzer W. Bioorg. Med. Chem. 2006; 14: 5061
• 24 Prokopp CR, Rubin MA, Sauzem PD, de Souza AH, Berlese DB, Lourega RV, Muniz MN, Bonacorso HG, Zanatta N, Martins MA. P, Mello CF. Braz. J. Med. Biol. Res. 2006; 39: 795
• 25a Patel MV, Bell R, Majest S, Henry R, Kolasa T. J. Org. Chem. 2004; 69: 7058
• 25b Süleyman H, Büyükokuroğlu ME. Biol. Pharm. Bull. 2001; 24: 1133
• 25c Balbi A, Anzaldi M, Mazzei M, Miele M, Bertolotto M, Ottonello L, Dallegri F. Bioorg. Med. Chem. 2006; 14: 5152
• 26 Shchegol’kov E, Khudina O, Anikina L, Burgart Ya, Saloutin V. Pharm. Chem. J. 2006; 40: 373
• 27 Bailey DM, Hansen PE, Hlavac AG, Baizman ER, Pearl J, Defelice AF, Feigenson ME. J. Med. Chem. 1985; 28: 256
• 28a Mahajan RN, Havaldar FH, Fernandes PS. J. Indian Chem. Soc. 1991; 68: 245
• 28b Dardari Z, Lemrani M, Sebban A, Bahloul A, Hassar M, Kitane S, Berrada M, Boudouma M. Arch. Pharm. 2006; 339: 291
• 29 Wardakhan WW, Louca NA. J. Chil. Chem. Soc. 2007; 52: 1145
• 30 Chauhan PM. S, Singh S, Chatterjee RK. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1993; 32: 858
• 31a Kurowski M, Dunky A, Geddawi M. Eur. J. Clin. Pharmacol. 1986; 31: 307
• 31b Leenen FH. H, Smith DL, Unger WP. Br. J. Clin. Pharmacol. 1988; 26: 481
• 32a Clark RD. J. Agric. Food Chem. 1996; 44: 3643
• 32b Vicentini CB, Guccione S, Giurato L, Ciaccio R, Mares D, Forlani G. J. Agric. Food Chem. 2005; 53: 3848
• 33a Chen H, Li Z, Han Y. J. Agric. Food Chem. 2000; 48: 5312
• 33b Vors J.-P, Gerbaud V, Gabas N, Canselier JP, Jagerovic N, Jimeno ML, Elguero J. Tetrahedron 2003; 59: 555
• 34a Finkelstein BL, Strock C. J. Pestic. Sci. 1997; 50: 324
• 34b Shiga Y, Okada I, Takizawa E, Fukuchi T. J. Pestic. Sci. 2003; 28: 313
• 35 Fahmy SM, Badran AH, Elnagdi MH. J. Chem. Tech. Biotechnol. 1980; 30: 390 ; Chem. Abstr. 1981, 94, 48804
• 36 Garcia H, Iborra S, Miranda MA, Morera IM, Primo J. Heterocycles 1991; 32: 1745
• 37 Shemyakina OA, Volostnykh OG, Stepanov AV, Ushakov IA, Mal’kina AG, Apartsin KA, Kireeva VV, Trofimov BA. ARKIVOC 2018; (v): 85
• 38 Lee YR, Kang KY, Lee GJ, Lee WK. Synthesis 2003; 1977
• 39 Garzino F, Méou A, Brun P. Eur. J. Org. Chem. 2003; 8: 1410
• 40a Kilroy TG, O’Sullivan TP, Guiry PJ. Eur. J. Org. Chem. 2005; 4929
• 40b Bera K, Ayyagari N, Satam N, Namboothiri IN. N. Org. Biomol. Chem. 2020; 18: 140
• 41 Bechthold AF.-W. Top. Curr. Chem. 1997; 188: 205
• 42 Bhat SV, Nagasampagi BA, Sivakumar M. Chemistry of Natural Products . Springer; Berlin/Heidelberg/New York: 2005: 840
• 43 Glycoscience: Chemistry and Chemical Biology I–III . Fraser-Reid BO, Tatsuta K, Thiem J. Springer-Verlag; Berlin/Heidelberg: 2012: 2872
• 44a Chimichi S, Boccalini M, Cosimelli B, Dall’Acqua F, Viola G. Tetrahedron 2003; 59: 5215
• 44b Rappai JP, Raman V, Unnikrishnan PA, Prathapan S, Thomas SK, Paulose CS. Bioorg. Med. Chem. Lett. 2009; 19: 764
• 44c Haung TT, Kirsch SF. Synthesis and Chemistry of 3(2H)-Furanones . In Targets in Heterocyclic Systems: Chemistry and Properties, Vol. 13. Attanasi OA, Spinelli D. Societa Chimica Italiana; Rome: 2009: 57
• 44d Amslinger S, Lindner SK. Synthesis 2011; 2671
• 44e Medvedev JJ, Semenok DV, Azarova XV, Rodina LL, Nikolaev VA. Synthesis 2016; 48: 4525
• 45 Egi M, Azechi K, Saneto M, Shimizu K, Akai S. J. Org. Chem. 2010; 75: 2123
• 46 Poonoth M, Krause N. J. Org. Chem. 2011; 76: 1934
• 47 Cao Z, Zhang R, Meng X, Li H, Li J, Zhu H, Chen G, Suna X, You J. RSC Adv. 2016; 6: 74582
• 48a Jackson RF. W, Raphael R. Tetrahedron Lett. 1983; 24: 2117
• 48b Felman SW, Jirkovsky I, Memoli KA, Borella L, Wells C, Russell J, Ward J. J. Med. Chem. 1992; 35: 1183
• 48c Villemin D, Jaffrès P.-A, Hachémi M. Tetrahedron Lett. 1997; 38: 537
• 48d Reiter M, Turner H, Mills-Webb R, Gouverneur V. J. Org. Chem. 2005; 70: 8478
• 49a Chimichi S, Boccalini M, Cravotto G, Rosati O. Tetrahedron Lett. 2006; 47: 2405
• 49b Crone B, Kirsch SF. J. Org. Chem. 2007; 72: 5435 ; and references therein
• 49c Chimichi S, Boccalini M, Salvador A, Dall’Acqua F, Basso G, Viola G. ChemMedChem. 2009; 4: 769
• 50a Takao K, Ochiai H, Yoshida K, Hashizuka T, Koshimura H, Tadano K, Ogawa S. J. Org. Chem. 1995; 60: 8179
• 50b Li Y, Hale KJ. Org. Lett. 2007; 9: 1267
• 51a Schmeda-Hirschmann G, Razmilic I, Sauvain M, Moretti C, Muñoz V, Ruiz E, Balanza E, Fournet A. Phytother. Res. 1996; 10: 375
• 51b Pertino M, Schmeda-Hirschmann G, Santos LS, Rodríguez JA, Theoduloz C. Z. Naturforsch. 2007; 62b: 275
• 52a Ishikawa M, Ninomiya T. J. Antibiot. 2008; 61: 692
• 52b Ishikawa M, Ninomiya T, Akabane H, Kushida N, Tsujiuchi G, Ohyama M, Gomi S, Shito K, Murata T. Bioorg. Med. Chem. 2009; 19: 1457
• 53 Trofimov BA, Shemyakina OA, Mal’kina AG, Ushakov IA, Kazheva ON, Alexandrov GG, Dyachenko OA. Org. Lett. 2010; 12: 3200
• 54a Shemyakina OA, Stepanov AV, Volostnykh OG, Mal’kina AG, Ushakov IA, Trofimov BA. Russ. J. Org. Chem. 2014; 50: 1617
• 54b Tietze LF. Chem. Rev. 1996; 1: 115
• 55 Mack RA, Zazulak WI, Radov LA, Baer JE, Stewart JD, Elzer PH, Kinsolving CR, Georgiev VS. J. Med. Chem. 1988; 31: 1910
• 56a Silverstein FE, Faich G, Goldstein JL, Simon LS, Pincus T, Whelton A, Makuch R, Eisen G, Agrawal NM, Stenson WF, Burr AM, Zhao WW, Kent JD, Lefkowith JB, Verburg KM, Geis GS. JAMA 2000; 284: 1247
• 56b Shamshina JL, Snowden TS. Tetrahedron Lett. 2007; 48: 3767
• 57 Carotti A, Carrieri A, Chimichi S, Boccalini M, Cosimelli B, Gnerre C, Carotti A, Carrupt P.-A, Testa B. Bioorg. Med. Chem. Lett. 2002; 12: 3551
• 58 Togashi M, Ozawa S, Abe S, Nishimura T, Tsuruga M, Ando K, Tamura G, Kuwahara S, Ubukata M, Magae J. J. Med. Chem. 2003; 46: 4113
• 59 Mal’kina AG, Volostnykh OG, Petrushenko KB, Shemyakina OA, Nosyreva VV, Ushakov IA, Trofimov BA. Tetrahedron 2013; 69: 3714
• 60 Mal’kina AG, Shemyakina OA, Stepanov AV, Volostnykh OG, Ushakov IA, Sobenina LN, Borodina TN, Smirnov VI, Trofimov BA. Synthesis 2016; 48: 271
• 61 Mal’kina AG, Stepanov AV, Sobenina LN, Shemyakina OA, Ushakov IA, Smirnov VI, Trofimov BA. Synthesis 2016; 48: 1880
• 62 Trofimov BA, Stepanov AV, Mal’kina AG, Volostnykh OG, Shemyakina OA, Ushakov IA. Synth. Commun. 2015; 45: 2718
• 63 Gryparis C, Lykakis IN, Efe C, Zaravinos I.-P, Vidali T, Kladou E, Stratakis M. Org. Biomol. Chem. 2011; 9: 5655
• 64a Yamada T, Kitada H, Kajimoto T, Numata A, Tanaka R. J. Org. Chem. 2010; 75: 4146
• 64b Ren H, Liu R, Chen L, Zhu T, Zhu WM, Gu QQ. Arch. Pharm. Res. 2010; 33: 499
• 65 Lu Q.-Q, Tian J.-M, Wei J, Gao J.-M. Nat. Prod. Res. 2014; 28: 1288
• 66 Hayashi Y, Sankar K, Ishikawa H, Nozawa Y, Mizoue K, Kakeya H. Bioorg. Med. Chem. Lett. 2009; 19: 3863
• 67 Orellana A, Rovis T. Chem. Commun. 2008; 730
• 68a Shin SS, Byun Y, Lim KM, Choi JK, Lee K.-W, Moh JH, Kim JK, Jeong YS, Kim JY, Choi YH, Koh H.-J, Park Y.-H, Oh YI, Noh M.-S, Chung S. J. Med. Chem. 2004; 47: 792
• 68b Bunnelle EM, Smith CR, Lee SK, Singaram SW, Rhodes AJ, Sarpong R. Tetrahedron 2008; 64: 7008
• 69 Trofimov BA, Andriyankova LV, Shaikhudinova SI, Kazantseva TI, Mal’kina AG, Afonin AV. Synthesis 2002; 853
• 70 Binder TJ, Crone B, Kirsch SF, Liébert C, Menz H. Eur. J. Org. Chem. 2007; 1636
• 71 Mal’kina AG, Volostnykh OG, Stepanov AV, Ushakov IA, Petrushenko KB, Trofimov BA. Synthesis 2013; 45: 3453
• 72 Kleemann A, Engel J, Kutscher B, Reichert D. In Pharmaceutical Substances: Syntheses, Patents, Applications, 4^th ed. Thieme; Stuttgart; 2001: see pages 361, 416, 1210, 2028 in particular
• 73 Trofimov BA, Sukhov BG, Gusarova NK, Malysheva SF, Mal’kina AG. Russ. J. Gen. Chem. 2002; 72: 1141
• 74 Arbuzova SN, Gusarova NK, Bogdanova MV, Ushakov IA, Mal’kina AG, Trofimov B. А. Mendeleev Commun. 2007; 17: 325
• 75a Parsons AF, Sharpe DJ, Taylor P. Synlett 2005; 2981
• 75b Arbuzova SN, Gusarova NK, Bogdanova MV, Ivanova NI, Ushakov IA, Mal’kina AG, Trofimov BA. Mendeleev Commun. 2005; 183
• 75c Arbuzova SN, Gusarova NK, Trofimov BA. ARKIVOC 2006; (v): 12
• 75d Niu M, Fu H, Jiang Y, Zhao Y. Chem. Commun. 2007; 272
• 75e Glotova TE, Dvorko MYu, Arbuzova SN, Ushakov IA, Verkhoturova SI, Gusarova NK, Trofimov BA. Lett. Org. Chem. 2007; 4: 109
• 75f Trofimov BA, Malysheva SF, Gusarova NK, Belogorlova NA, Vasilevsky SF, Kobychev VB, Sukhov BG, Ushakov IA. Mendeleev Commun. 2007; 181
• 76a Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications. Börner A. Wiley-VCH; Weinheim: 2008: 1
• 76b Freixa Z, van Leeuwen PW. N. M. Coord. Chem. Rev. 2008; 252: 1755
• 76c Birkholz MN, Freixa Z, van Leeuwen PW. N. M. Chem. Soc. Rev. 2009; 38: 1099
• 76d Chatterjee S, Patel SK, Tirkey V, Mobin SM. J. Organomet. Chem. 2012; 699: 12
• 77 Arbuzova SN, Gusarova NK, Verkhoturova SI, Kazantseva TI, Ushakov IA, Mal’kina AG, Trofimov BA. Heteroat. Chem. 2015; 26: 231
• 78 Oparina LA, Shabalin DA, Mal’kina AG, Kolyvanov NA, Grishchenko LA, Ushakov IA, Vashchenko AV, Trofimov BA. Eur. J. Org. Chem. 2020; 4181
• 79a Noda K, Murata M. Biosci. Biotech. Biochem. 2017; 81: 343
• 79b Ghirardi E, Griera R, Picciche M, Molins E, Fernandez I, Bosch J, Amat M. Org. Lett. 2016; 18: 5836
• 79c Szalóki G, Sanguinet L. J. Org. Chem. 2015; 80: 3949
• 79d Tao Q, Tang G, Lin K, Zhao Y.-F. Chirality 2008; 20: 833
• 79e Radford PA, Attygalle B, Meinwald J. J. Nat. Prod. 1997; 60: 755
• 79f Romo D, Meyers AI. Tetrahedron 1991; 47: 9503
• 79g Petchnaree P, Bunyaprahatsara N, Cordell GA, Cowe HJ, Cox PJ, Howie RA, Patt SL. J. Chem. Soc., Perkin Trans. 1 1986; 1551
• 80a Chen W.-L, Wang L.-Y, Li Y.-J. Eur. J. Org. Chem. 2020; 103
• 80b Jung ME, Chang JJ. Org. Lett. 2010; 12: 2962
• 80c Saito M, Kuwahara S. Biosci. Biotechnol. Biochem. 2005; 69: 374
• 80d O’Hagan D. Nat. Prod. Rep. 2000; 17: 435
• 80e Groaning MD, Meyers AI. Tetrahedron 2000; 56: 9843
• 80f Degnan AP, Meyers AI. J. Am. Chem. Soc. 1999; 121: 2762
• 80g Arrington MP, Meyers AI. Chem. Commun. 1999; 1371
• 80h Meyers AI, Harre M, Garland R. J. Am. Chem. Soc. 1984; 106: 1146
• 81a Oparina LA, Shabalin DA, Kolyvanov NA, Ushakov IA, Mal’kina AG, Vashchenko AV, Trofimov BA. Tetrahedron Lett. 2019; 60: 334
• 81b Oparina LA, Shabalin DA, Kolyvanov NA, Ushakov IA, Trofimov BA. Russ. J. Org. Chem. 2018; 54: 1848
• 82a Meyers AI, Lefker BA, Sowin TJ, Westrum LJ. J. Org. Chem. 1989; 54: 4243
• 82b Higashiyama K, Inoue H, Takahashi H. Tetrahedron 1994; 50: 1083
• 82c Husson H.-P, Royer J. Chem. Soc. Rev. 1999; 28: 383
• 82d Katritzky AR, Cui X.-L, Yang B, Steel PJ. J. Org. Chem. 1999; 64: 1979
• 82e Alladoum J, Roland S, Vrancken E, Mangeney P, Kadouri-Puchot C. J. Org. Chem. 2008; 73: 9771
• 82f Rahman M, Bagdi AK, Mishra S, Hajra A. Chem. Commun. 2014; 50: 2951
• 82g Lubin H, Pytkowicz J, Chaume G, Sizun-Thomé G, Brigaud T. J. Org. Chem. 2015; 80: 2700
• 83 Oparina LA, Kolyvanov NA, Ushakov IA, Mal’kina AG, Vashchenko AV, Trofimov BA. Synthesis 2019; 51: 1445
• 84a Kobayashi S, Peng G, Fukuyama T. Tetrahedron Lett. 1999; 40: 1519
• 84b Herold F, Krol M, Kleps J. Acta Pol. Pharm. 2004; 61: 139
• 84c Shimogawa H, Kuribayashi S, Teruya T, Suenaga K, Kigoshi H. Tetrahedron Lett. 2006; 47: 1409
• 84d Mohamed MS, El-Domany RA, El-Hameed RH. Acta Pharm. 2009; 59: 145
• 84e Jones SB, Simmons B, Mastracchio A, MacMillan DW. C. Nature 2011; 475: 183
• 84f Suzuki T, Kubota T, Kobayashi J. Bioorg. Med. Chem. Lett. 2011; 21: 4220
• 84g Tiong S, Looi C, Hazni H, Arya A, Paydar M, Wong W, Cheah S.-C, Mustafa M, Awang K. Molecules 2013; 18: 9770
• 84h Ghorab MM, Alsaid MS. Biomed. Res. 2015; 26: 420
• 85a Sanguinet L, Pozzo J.-L, Rodriguez V, Adamietz F, Castet F, Ducasse L, Champagne B. J. Phys. Chem. B 2005; 109: 11139
• 85b Mancois F, Pozzo J.-L, Adamietz F, Rodriguez V, Ducasse L, Castet F, Plaquet A, Champagne B. Chem. Eur. J. 2009; 15: 2560
• 85c Szalóki G, Alévêque O, Pozzo J.-L, Hadji R, Levillain E, Sanguinet L. J. Phys. Chem. B 2015; 119: 307
• 85d Bondu F, Quertinmont J, Rodriguez V, Pozzo J.-L, Plaquet A, Champagne B, Castet F. Chem. Eur. J. 2015; 21: 18749
• 85e Pielak K, Bondu F, Sanguinet L, Rodriguez V, Champagne B, Castet F. J. Phys. Chem. C. 2017; 121: 1851
• 86a Mancois F, Sanguinet L, Pozzo J.-L, Guillaume M, Champagne B, Rodriguez V, Adamietz F, Ducasse L, Castet F. J. Phys. Chem. B. 2007; 111: 9795
• 86b Sevez G, Gan J, Delbaere S, Vermeersch G, Sanguinet L, Levilain E, Pozzo J.-L. Photochem. Photobiol. Sci. 2010; 9: 131
• 86c Szalóki G, Sanguinet L. Properties and Applications of Indolinooxazolidines as Photo-, Electro-, and Acidochromic Units. In Photon-Working Switches. Yokoyama Y, Nakatani K. Springer Japan; Tokyo: 2017: 69
• 87a Guanidines, Amidines, Phosphazenes and Related Organocatalysts: Superbases for Organic Synthesis. Ishikawa T. John Wiley & Sons; Chichester: 2009: 20
• 87b Taylor JE, Bull SD, Williams JM. J. Chem. Soc. Rev. 2012; 41: 2109
• 87c Li A, Lu L, Li X, He L, Do C, Garno JC, Zhang D. Macromolecules 2016; 49: 1163
• 87d Wu T, Bu X, Liao P, Wang L, Zheng ST, Ma R, Feng P. J. Am. Chem. Soc. 2012; 134: 3619
• 88a Perez ER, Santos RH. A, Gambardella MT. P, de Macedo LG. M, Rodrigues-Filho UP, Launay J.-C, Franco DW. J. Org. Chem. 2004; 69: 8005
• 88b Yadav M, Linehan JC, Karkamkar AJ, van der Eide E, Heldebrant DJ. Inorg. Chem. 2014; 53: 9849
• 89a Lönnqvist J.-ES, Jalander LF. J. Chem. Res., Synop. 2000; 102
• 89b Im YJ, Gong JH, Kim HJ, Kim JN. Bull. Korean Chem. Soc. 2001; 22: 1053
• 89c Bulman Page PC, Vahedi H, Bethell D, Barkley JV. Synth. Commun. 2003; 33: 1937
• 89d Gierczyk B, Schroeder G, Brzezinski B. J. Org. Chem. 2003; 68: 3139
• 89e Heldebrant DJ, Jessop PG, Thomas CA, Eckert CA, Liotta CL. J. Org. Chem. 2005; 70: 5335
• 89f Gryko DT, Piechowska J, Tasior M, Waluk J, Orzanowska G. Org. Lett. 2006; 8: 4747
• 89g Nirmala R, Ponpandian T, Venkatraman BR, Rajagopal S. Tetrahedron Lett. 2013; 54: 5181
• 89h Mishra R, Panini P, Sankar J. Org. Lett. 2014; 16: 3994
• 89i Baravkar SB, Roy A, Gawade RL, Puranik VG, Sanjayan GJ. Synth. Commun. 2014; 44: 2955
• 89j Poronik YM, Gryko DT. Chem. Commun. 2014; 50: 5688
• 89k Chen J, Natte K, Wu X.-F. Tetrahedron Lett. 2015; 56: 342
• 90a Ma L, Dolphin D. J. Chem. Soc., Chem. Commun. 1995; 2251
• 90b Nie L.-Q, Shi Z.-J, Cao W.-Q. Bopuxue Zazhi 2002; 19: 377
• 90c Shi Z.-J, Nie L.-Q. Fenxi Huaxue 2003; 31: 573
• 90d Shi Z.-J, Nie L.-Q, Cao W.-Q. Fenxi Kexue Xuebao 2004; 20: 586
• 91a Trofimov BA, Shemyakina OA, Mal’kina AG, Stepanov AV, Volostnykh OG, Ushakov IA, Vashchenko AV. Eur. J. Org. Chem. 2016; 33: 5465
• 91b Shemyakina OA, Volostnykh OG, Stepanov AV, Mal’kina AG, Ushakov IA, Apartsin KA, Kireeva VV, Trofimov BA. Mendeleev Commun. 2018; 28: 128
• 92 Trofimov BA, Andriyankova LV, Tlegenov RT, Mal’kina AG, Afonin AV, Il’icheva LN. Mendeleev Commun. 2005; 33
• 93 Dwoskin LP, Teng L, Buxton ST, Ravard A, Deo N, Crooks PA. Eur. J. Pharmacol. 1995; 276: 195
• 94 Andriyankova LV, Mal’kina AG, Afonin AV, Trofimov BA. Mendeleev Commun. 2003; 186
• 95 Andriyankova LV, Mal’kina AG, Nikitina LP, Belyaeva KV, Ushakov IA, Afonin AV, Nikitin MV, Trofimov BA. Tetrahedron 2005; 61: 8031
• 96a Hohmann J, Forgo P, Szabo P. Fitoterapia 2002; 73: 749
• 96b Gonzaga W, Weber AD, Giacomelli SR, Dalcol II, Hoelzel SC. Planta Med. 2003; 69: 371
• 96c Huber R, Amann N, Wagenknecht HA. J. Org. Chem. 2004; 69: 744
• 96d Torres JC, Pinto AC, Garden SJ. Tetrahedron 2004; 60: 9889
• 97 Trofimov BA, Mal’kina AG, Nosyreva VV, Shemyakina OA, Albanov AI, Afonin AV, Kazheva ON, Alexandrov GG, Dyachenko OA. Tetrahedron Lett. 2012; 53: 927
• 98 Trofimov BA, Andriyankova LV, Zhivet’ev SA, Mal’kina AG, Voronov VK. Tetrahedron Lett. 2002; 43: 1093
• 99 Trofimov BA, Andriyankova LV, Mal’kina AG, Belyaeva KV, Nikitina LP, Baikalova LV. Mendeleev Commun. 2007; 237
• 100 Trofimov BA, Andriyankova LV, Mal’kina AG, Belyaeva KV, Nikitina LP, Dayachenko OA, Kazheva ON, Chekhlov AN, Shilov GV, Afonin AV, Ushakov IA, Baikalova LV. Eur. J. Org. Chem. 2007; 1018
• 101 Andriyankova LV, Belyaeva KV, Nikitina LP, Mal’kina AG, Afonin AV, Trofimov BA. Synthesis 2010; 2828
• 102 Trofimov BA, Andriyankova LV, Nikitina LP, Belyaeva KV, Mal’kina АG, Afonin AV. Synthesis 2010; 1536
• 103a Chandra T, Brown KL. Tetrahedron Lett. 2005; 46: 8617
• 103b Chandra T, Brown KL. Tetrahedron 2008; 64: 9
• 104 VanVliet DS, Gillespie P, Scicinski JJ. Tetrahedron Lett. 2005; 46: 6741
• 105 Legros J, Dehli JR, Bolm C. Adv. Synth. Catal. 2005; 347: 19
• 106 Sun L.-N, Chen Y.-W, Ying Y.-W, Li D, Li T.-F, Zhang X.-H, Zhao P, Ding L, Zhao Y.-Q. Chirality 2018; 30: 1277
• 107 Sann GL, Baron A, Mann J, Berg H, Gunaratham M, Neidle S. Org. Biomol. Chem. 2006; 4: 1305
• 108 Kobayashi K, Fukunishi H, Umishio K, Tajima M. EP 989123 A1, 2000 ; Chem. Abstr. 2000, 132, 251150
• 109 Wahe H, Asobo PF, Cherkasov RA, Fomum ZT, Doepp D. ARKIVOC 2004; (i): 130
• 110 Trofimov BA, Mal’kina AG, Shemyakina OA, Borisova AP, Nosyreva VV, Dyachenko OA, Kazheva ON, Alexandrov GG. Synthesis 2007; 2641
• 111a Niece KL, Hartgerink JD, Donners JJ. J. M, Stupp SI. J. Am. Chem. Soc. 2003; 125: 7146
• 111b Bull SR, Guler MO, Bras RE, Venkatasubramanian PN, Stupp SI, Meade TJ. Bioconjugate Chem. 2005; 16: 1343
• 111c Behanna HA, Donners JJ. J. M, Gordon AC, Stupp SI. J. Am. Chem. Soc. 2005; 127: 1193
• 111d Guler MO, Soukasene S, Hulvat JF, Stupp SI. Nano Lett. 2005; 5: 249
• 112a Schacht M, Boehlich GJ, de Vries J, Bertram S, Gabriel G, Zimmermann P, Heisig P, Schützenmeister N. Eur. J. Org. Chem. 2017; 1745
• 112b Schacht M, Mohammadi D, Schützenmeister N. Eur. J. Org. Chem. 2019; 2587
• 113 Mal’kina AG, Borisova AP, Nosyreva VV, Shemyakina OA, Albanov AI, Trofimov BA. ARKIVOC 2011; (ix): 281
• 114 Chachin M, Yamada M, Fujita A, Matsuoka T, Matsushita K, Kurachi Y. JPET 2003; 304: 1025
• 115 Wosikowski-Buters K, Sperl S, Sommer J. Patent WO2004011449 A2, 2004 ; Chem. Abstr. 2004, 140, 146510
• 116 Williams R, Holyoak T, McDonald G, Gui C, Fenton AW. Biochemistry 2006; 45: 5421
• 117a Easton CJ, Harper JB. Tetrahedron Lett. 1998; 39: 5269
• 117b Boger DL. Med. Res. Rev. 2001; 21: 356
• 118a Makino S, Okuzumi T, Yoshimura T, Satake Y, Suzuki N, Izawa H, Sagi K, Chiba A, Nakanishi E, Murata M, Tsuji T. Patent WO2002016329 A1, 2002 ; Chem. Abstr. 2002, 136, 217047
• 118b Okuzumi T, Sagi K, Yoshimura T, Tanaka Y, Nakanishi E, Ono M, Murata M. Patent WO2003053926 А1, 2003 ; Chem. Abstr. 2003, 139, 85646
• 119 Trofimov BA, Mal’kina AG, Borisova AP, Shemyakina OA, Nosyreva VV, Albanov AI. Synthesis 2010; 3174
• 120 De Sa Alves FR, Barreiro EJ, Fraga CA. M. Mini-Rev. Med. Chem. 2009; 9: 782
• 121 Conigrave AD, Quinn SJ, Brown EM. PNAS 2000; 97: 4814
• 122a Friedman M, Cug J.-L. J. Agric. Food Chem. 1988; 36: 1079
• 122b Lee DG, Cho NJ, Choi JD. J. Biochem. Mol. Biol. 1996; 29: 321
• 122c Murch SJ, KrishnaRaj S, Saxena PK. Plant Cell Rep. 2000; 19: 698
• 122d Hirasawa M, Nakayama M, Kim S.-K, Hase T, Knaff DB. Photosynth. Res. 2005; 86: 325
• 122e Bender J, Celenza JL. Phytochem. Rev. 2009; 8: 25
• 123 Somei M, Hattori A, Suzuki N. Patent WO2007010723 А1, 2007 ; Chem. Abstr. 2007, 146, 163392
• 124 Walther D, Bader M. Patent WO2002074309 А2, 2002 ; Chem. Abstr. 2002, 137, 242150
• 125 Watanabe F. Patent WO2001055133 A1, 2001 ; Chem. Abstr. 2001, 135, 137709
• 126 Mal’kina AG, Nosyreva VV, Shemyakina OA, Borisova AP, Albanov AI, Tatarinova AA, Trofimov BA. Russ. Chem. Bull. 2013; 62: 2538
• 127 Cao G, Bandelac L, Volgina A, Korostoff J, Di-Rienzo JM. Infect. Immun. 2008; 76: 2812
• 128 Romanova TA, Krasnov PO, Kuzubov AA, Avramov PV. Russ. J. Bioorg. Chem. 2004; 30: 124
• 129 Deplazes E, van Bronswijk W, Zhu F, Barron LD, Ma S, Nafie LA, Jalkanen KJ. Theor. Chem. Acc. 2008; 119: 155
• 130 Conigrave AD, Quinn SJ, Brown EM. Proc. Natl. Acad. Sci. U. S. A. 2000; 97: 4814
• 131 Kleemann A, Engel J, Kutscher B, Reichert D. Pharmaceutical Substances: Syntheses, Patents, Applications, 4th ed. Thieme; Stuttgart: 2001: 1015
• 132 Gusev GA, Gaobin Z, Kobayashi K, Jianhua K, Moiseenko EV, Polukhina NG, Saitoe T, Tao E, Tsarev VA, Huang Y. Bull. Lebedev Phys. Inst. 2008; 35: 247
• 133 Remko M, Fitz D, Rode BM. Amino Acids 2010; 39: 1309
• 134 Pickup ME, Dixon JS, Lowe JR, Wright V. J. Rheumatol. 1980; 7: 71
• 135 Mashkovskii MD. In Lekarstvennye Sredstva, 14th ed., Vol. 2; (in Russian). Novaya Volna; Moscow: 2003: 124
• 136 Rauen U, Klempt S, de Groot H. Cell. Mol. Life Sci. 2007; 64: 192
• 137 Bokeriya LA, Boldyrev AA, Movsesyan RR, Alikhanov SA, Arzumanyan ES, Nisnevich ED, Artyukhina TV, Serov RA. Bull. Exp. Biol. Med. 2008; 145: 323
• 138 Trofimov BA, Mal’kina AG, Shemyakina OA, Nosyreva VV, Borisova AP, Albanov AI, Kazheva ON, Alexandrov GG, Chekhlov AN, Dyachenko OA. Tetrahedron 2009; 65: 2472
• 139 Shemyakina OA, Mal’kina AG, Nosyreva VV, Ushakov IA, Trofimov BA. ARKIVOC 2012; (viii): 319
• 140 Madrakian T, Afkhami A, Khalafi L, Mohammadnejad M. J. Braz. Chem. Soc. 2006; 17: 1259
• 141a Etzbach K.-H, Freund T, Tresh R. German Patent DE19851026 A1, 2000 ; Chem. Abstr. 2000, 132, 348991
• 141b Bindra AP. Patent WO2001036541 A1, 2001 ; Chem. Abstr. 2001, 134: 368256
• 142a Smets J, Trujillo R, Fredj A, White DJ. Jr, Boswell RW. Jr, Ridley G. Patent WO2002092746, 2002 ; Chem. Abstr. 2002, 137, 386349
• 142b Vlad FJ, Mounier R, Wong K, Daugeron A, Herd T. Patent US20060084589, 2006 ; Chem. Abstr. 2006, 144, 397678
• 143a Lehmann T, Albers M, Rölle T, Müller G, Hebler G, Tajimi M, Ziegelbauer K, Okigami H. Patent WO2003030889, 2003 ; Chem. Abstr. 2003, 138, 321573
• 143b Abd El Wahed MG, Abd El Wanees S, El Gamel M, Abd El Haleem S. J. Serb. Chem. Soc. 2004; 69: 255
• 143c Varnavas A, Lassiani L, Valenta V, Mennuni L, Makovec F, Hadjipavlou-Litina D. Eur. J. Med. Chem. 2005; 40: 563
• 143d Correa-Basurto J, Vázquez Alcántara I, Espinoza-Fonseca LM, Trujillo-Ferrara JG. Eur. J. Med. Chem. 2005; 40: 732
• 143e Shen HC, Ding F.-X, Luell S, Forrest MJ, Carbollo-Jane E, Wu KK, Wu T.-J, Cheng K, Wilsie LC, Krsmanovic ML, Taggart AK, Ren N, Cai T.-Q, Deng Q, Chen Q, Wang J, Wolff MS, Tonq X, Holt TG, Waters MG, Hammond ML, Tata JR, Colleti SL. J. Med. Chem. 2007; 50: 6303
• 144 Robert D, Jung L. Patent EP235064 A2, 1987 ; Chem. Abstr. 2001, 109, 11585
• 145a Ito AS, de Souza ES, Barbosa SR, Nakaie CR. Biophys. J. 2001; 81: 1180
• 145b Wang Q, Yan B. J. Mater. Chem. 2004; 14: 2450
• 146 Trofimov BA, Mal’kina AG, Shemyakina OA, Nosyreva VV, Borisova AP, Kazheva ON, Alexandrov GG, Dyachenko OA. Mendeleev Commun. 2008; 18: 278
• 147a Mashkovskii MD. In Lekarstvennye Sredstva, 14th ed., Vol. 2; (in Russian). Novaya Volna; Moscow: 2003: 306
• 147b Lourenco MC. S, de Souza MV. N, Pinheiro AC, Ferreira M. deL, Goncalves RS. B, Nogueira TC. M, Peralta MA. ARKIVOC 2007; (xv): 181
• 148 de Souza MV. N. Recent Pat. Anti-Infective Drug Discovery 2006; 1: 33
• 149 Trofimov BA, Mal’kina AG, Shemyakina OA, Nosyreva VV, Borisova AP, Khutsishvili SS, Krivdin LB. Synthesis 2009; 3136
• 150 Wang X, Guo Z. Anti-Cancer Agents Med. Chem. 2007; 7: 19
• 151a Mashkovskii MD. In Lekarstvennye Sredstva, 14th ed., Vol. 2; (in Russian). Novaya Volna; Moscow: 2003: 125
• 151b Zhou NE, Reddy AV. N, Kaleta J, Micetich RG, Singh R. ARKIVOC 2001; (vi): 116
• 151c Hsu C.-C, Huang C.-N, Hung Y.-C, Yin M.-C. J. Nutr. 2004; 134: 149
• 151d Ali V, Nozaki T. Clin. Microbiol. Rev. 2007; 164 ; and references cited therein
• 152 Riedijk MA, Stoll B, Chacko S, Schierbeek H, Sunehag AL, van Goudoever JB, Burrin DG. Proc. Natl. Acad. Sci. U. S. A. 2007; 104: 3408
• 153 Trofimov BA, Mal’kina AG, Nosyreva VV, Shemyakina OA, Borisova AP, Larina LI, Kazheva ON, Alexandrov GG, Dyachenko OA. Tetrahedron 2010; 66: 1699
• 154a Contreras JG, Marariada ST, Alderete JB. J. Mol. Struct. THEOCHEM 1996; 365: 63
• 154b Contreras JG, Marariada ST, Alderete JB. J. Phys. Org. Chem. 1998; 11: 392
• 155a Gi H.-J, Xiang Y, Schinazi RF, Zhao K. J. Org. Chem. 1997; 62: 88
• 155b Ciapetti P, Taddei M. Tetrahedron 1998; 54: 11305
• 155c Guan H.-P, Ksebati MB, Kern ER, Zemlicka J. J. Org. Chem. 2000; 65: 5177
• 156a Yashima E, Suehiro N, Akashi M, Miyauchi N. Chem. Lett. 1990; 1113
• 156b Yashima E, Tajima T, Miyauchi N, Akashi M. Biopolymers 1992; 32: 811
• 157a Montgomery JA, Shortnacy AT, Secrist JA. III. J. Med. Chem. 1983; 26: 1483
• 157b Rose JD, Parker WB, Someya H, Shaddix SC, Montgomery JA, Secrist JA. III. J. Med. Chem. 2002; 45: 4505
• 157c Pramod G, Mohan H, Manoj P, Manojkumar TK, Manoj VM, Mital JP, Aravindakumar CT. J. Phys. Org. Chem. 2006; 19: 415
• 158 Berens RL, Marr JJ. Biochem. Pharmacol. 1986; 35: 4191
• 159 Mal’kina AG, Nosyreva VV, Shemyakina OA, Albanov AI, Trofimov BA. Mendeleev Commun. 2017; 27: 14
• 160a Kleemann A, Engel J, Kutscher B, Reichert D. Pharmaceutical Substances: Syntheses, Patents, Applications, 4th ed. Thieme; Stuttgart: 2001: 332-333 ; see also pages 956-958
• 160b Smee DF, Bailey KW, Sidwell RW. Chemotherapy 2003; 49: 126
• 160c Baldanti F, Gerna G. J. Antimicrob. Chemother. 2003; 52: 324
• 160d Smee DF, Wandersee MK, Bailey KW, Hostetler KY, Holy A, Sidwell RW. Antiviral Chem. Chemother. 2005; 16: 203
• 160e De Clercq E, Holý A. Nat. Rev. Drug Discovery 2005; 4: 928
• 160f Holý A. Antiviral Res. 2006; 71: 248
• 161a Lindsell WE, Murray C, Preston PN, Woodman TA. J. Tetrahedron 2000; 56: 1233
• 161b Redwane N, Lazrek HB, Barascut JL, Imbach JL, Balzarini J, Witvrouw M, De Clercq E. Nucleosides, Nucleotides Nucleic Acids 2001; 20: 1439
• 161c Guillarme S, Legoupy S, Bourgougnon N, Aubertin A.-M, Huet F. Tetrahedron 2003; 59: 9635
• 161d Wójtowicz-Rajchel H, Koroniak H, Katrusiak A. Eur. J. Org. Chem. 2008; 368
• 162 Mashkovskii MD. In Lekarstvennye Sredstva, 14th ed., Vol. 2; (in Russian). Novaya Volna; Moscow: 2003: 330
• 163a Nomura M, Shuto S, Matsuda A. Bioorg. Med. Chem. 2003; 11: 2453
• 163b Moiseev DV, Marchenko SI, Moiseeva AM, Truhacheva TV, Petrov PT, Zhebentyaev AI. Pharm. Chem. J. 2007; 41: 25
• 164 Trofimov BA, Nosyreva VV, Shemyakina OA, Mal’kina AG, Albanov AI. Tetrahedron Lett. 2012; 53: 5769
• 165a Robins MJ, Miles RW, Samano MC, Kaspar RL. J. Org. Chem. 2001; 66: 8204
• 165b Nguyen-Trung NQ, Botta O, Terenzi S, Strazewski P. J. Org. Chem. 2003; 68: 2038
• 166 Robins MJ, Peng Y, Damaraju VL, Mowles D, Barron G, Tackaberry T, Young JD, Cass CE. J. Med. Chem. 2010; 53: 6040
• 167a Wnuk SF, Valdez CA, Khan J, Moutinho P, Robins MJ, Yang X, Borchardt RT, Balzarini J, De Clercq E. J. Med. Chem. 2000; 43: 1180
• 167b Wnuk SF, Ro B.-O, Valdez CA, Lewandowska E, Valdez NX, Sacasa PR, Yin D, Zhang J, Borchardt RT, De Clercq E. J. Med. Chem. 2002; 45: 2651
• 167c Wnuk SF, Lewandowska E, Sacasa PR, Crain LN, Zhang J, Borchardt RT, De Clercq E. J. Med. Chem. 2004; 47: 5251
• 168a Pandit UK, Grose WF. A, Eggelte TA. Synth. Commun. 1972; 2: 345
• 168b De Clercq E, Holy A. J. Med. Chem. 1979; 22: 510
• 168c Wnuk SF, Yuan C.-S, Borchardt RT, Balzarini J, De Clercq E, Robins MJ. J. Med. Chem. 1994; 37: 3579
• 168d Wnuk SF, Yuan C.-S, Borchardt RT, Balzarini J, De Clercq E, Robins MJ. J. Med. Chem. 1997; 40: 1608
• 168e Hecker SJ, Reddy KR, van Poelje PD, Sun Z, Huang W, Varkhedkar V, Reddy MV, Fujitaki JM, Olsen DB, Koeplinger KA, Boyer SH, Linemeyer DL, MacCoss M, Erion MD. J. Med. Chem. 2007; 50: 3891
• 169 Rapp M, Haubrich TA, Perrault J, Mackey ZB, McKerrow JH, Chiang PK, Wnuk SF. J. Med. Chem. 2006; 49: 2096
• 170a Odijk WM, Koomen GJ. Tetrahedron 1985; 41: 1893
• 170b Odijk WM, Koomen GJ. Histochem. Cytochem. 1987; 35: 1161
• 171a Thome F, Blois F, Olomucki A, Olomucki M. Eur. J. Biochem. 1987; 162: 433
• 171b Liu S, Wnuk SF, Yuan C.-S, Robins MJ, Borchardt RT. J. Med. Chem. 1993; 36: 883
• 171c Wanner MJ, Deghati PY. F, Rodenko B, Koomen GJ. Pure Appl. Chem. 2000; 72: 1705
• 171d Wanner MJ, Von Frijtag Drabbe Künzel JK, Ijzerman AP, Koomen G.-J. Bioorg. Med. Chem. Lett. 2000; 10: 2141
• 172 Nosyreva VV, Mal’kina AG, Volostnykh OG, Albanov AI, Trofimov BA. Synthesis 2013; 45: 3263
• 173a Furukawa Y, Miyashita O, Honjo M. Chem. Pharm. Bull. 1974; 22: 2552
• 173b Olomucki M, Le Gall JY, Colinart S. Tetrahedron Lett. 1984; 25: 3471
• 173c Roques P, Le Gall JY, Lacombe L, Olomucki M. J. Org. Chem. 1992; 57: 1579
• 174a Hattori H, Tanaka M, Fukushima M, Sasaki T, Matsuda A. J. Med. Chem. 1996; 39: 5005
• 174b Hattori H, Nozawa E, Iino T, Yoshimura Y, Shuto S, Shimamoto Y, Nomura M, Fukushima M, Tanaka M, Sasaki T, Matsuda A. J. Med. Chem. 1998; 41: 2892
• 174c Matsuda A, Sasaki T. Cancer Sci. 2004; 95: 105
• 174d Murata D, Endo Y, Obata T, Sakamoto K, Syouji Y, Kadohira M, Matsuda A, Sasaki T. Drug Metab. Dispos. 2004; 32: 1178
• 174e Yonemura Y, Endo Y, Obata T, Sasaki T. Cancer Sci. 2007; 98: 11
• 174f Meike S, Yamamori T, Yasui H, Eitaki M, Matsuda A, Morimatsu M, Fukushima M, Yamasaki Y, Inanamil O. Mol. Cancer 2011; 10: 92
• 175 Das P, Wolff RA, Abbruzzese JL, Varadhachary GR, Evans DB, Vauthey JN, Baschnagel A, Delclos ME, Krishnan S, Janjan NA, Crane CH. Radiat. Oncol. 2006; 1: 41
• 176 Ando T, Ichikawa J, Okamoto A, Tasaka K, Nakao A, Hamada Y. J. Orthop. Res. 2005; 23: 964
• 177a Crane CM, Hirsch AK. H, Alphey MS, Sgraja T, Lauw S, Illarionova V, Rohdich F, Eisenreich W, Hunter WN, Bacher A, Diederich F. ChemMedChem 2008; 3: 91
• 177b Krasuski A, Michnowska-Swincow E, Jarzembowski T. Lett. Appl. Microbiol. 2007; 497
• 177c Gu T, Zhao S, Pi Y, Chen W, Chen C, Liu Q, Li M, Han D, Ji Q. Chem. Sci. 2018; 9: 3248
• 177d Bhattacharyya T, Chaudhuri R, Das KS, Mondal R, Mandal S, Dash J. ACS Appl. Bio Mater. 2019; 3171
• 178 Nosyreva VV, Mal’kina AG, Albanov AI, Trofimov BA. Tetrahedron Lett. 2014; 50: 5426
• 179a Kleemann A, Engel J, Kutscher B, Reichert D. Pharmaceutical Substances: Syntheses, Patents, Applications . Thieme; Stuttgart: 2001: 31-32 ; see also pages 954-955
• 179b Mashkovskii MD. In Lekarstvennye Sredstva, 14th ed., Vol. 2, (in Russian) 2003; 331
• 179c Aleksandrova EV, Kochergin PM. Chem. Heterocycl. Compd. 2009; 1
• 180 Khropov YV, Pinchuk NYa, Baranova LA, Tunitskaya VL, Kochetkov SN. RU Patent 2035468, 1990 ; Chem. Abstr. 1995, 124, 139766
• 181 Korovina AN, Yas’ko MV, Ivanov AV, Handazhinskaya AL, Karamov EV, Kornilova GV, Kukhanova MK. Vestn. Mosk. Univ., Ser. 2: Khim. 2008; 49: 108 ; Chem. Abstr. 2008, 150, 352422
• 182a Tanaka N, Wu RT, Okabe T, Yamashita H, Shimazu A, Nishimura T. J. Antibiot. 1982; 35: 272
• 182b Yuan BD, Wu RT, Sato I, Okabe T, Suzuki H, Nishimura T, Tanaka N. J. Antibiot. 1985; 38: 642
• 182c Kondo T, Okamoto K, Yamamoto M, Goto T, Tanaka N. Tetrahedron 1986; 42: 199
• 182d Tumkevicius S, Dodonova J. Chem. Heterocycl. Compd. 2012; 258
• 183a Collins P, Baner DJ. J. Antimicrob. Chemother. 1979; 5: 431
• 183b Fomina AN, Nikolaeva IS, Pushkina TV, Mazan’ko TK, Filatov FP. Pharm. Chem. J. 1986; 20: 140
• 183c Studentsov EP, Gemkin DD, Burlakov SD, Tets VV, Surkov KG. RU Patent 2111967, 1996 ; Chem. Abstr. 1998, 132, 322076
• 183d De Clercq E, Andrei G, Snoeck R, De Bolle L, Naesens L, Degrève B, Balzarini J, Zhang Y, Schols D, Leyssen P, Ying C, Neyts J. Nucleosides, Nucleotides Nucleic Acids 2001; 20: 271