Synthesis 2015; 47(23): 3733-3740
DOI: 10.1055/s-0035-1560184
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 5H-Pyrrolo[3,4-b]pyrazine-Based Peptidomimetics

Angelina V. Biitseva
a   Department of Chemistry, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrs’ka str., Kyiv 01601, Ukraine   eMail: ov_hordiyenko@univ.kiev.ua
,
Igor V. Rudenko
a   Department of Chemistry, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrs’ka str., Kyiv 01601, Ukraine   eMail: ov_hordiyenko@univ.kiev.ua
,
Olga V. Hordiyenko*
a   Department of Chemistry, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrs’ka str., Kyiv 01601, Ukraine   eMail: ov_hordiyenko@univ.kiev.ua
,
Iryna V. Omelchenko
b   SSI ‘Institute for Single Crystals’, National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv 61072, Ukraine
,
Axelle Arrault
c   Laboratoire de Chimie Physique Macromoléculaire, ENSIC, Université de Lorraine, 1 rue Grandville, BP 20451, 54001 Nancy, France
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Publikationsverlauf

Received: 28. Mai 2015

Accepted after revision: 30. Juli 2015

Publikationsdatum:
16. September 2015 (online)


Dedicated to Professor Mykhailo Yu. Kornilov on the occasion of his retirement

Abstract

A range of 5H-pyrrolo[3,4-b]pyrazine-based peptidomimetics were designed, and their efficient synthesis starting from 5-imino-5H-pyrrolo[3,4-b]pyrazin-7-amine by subsequent interaction with N-protected amino acid hydrazides and amino acid esters with N,N-carbonyldiimidazole as the coupling agent was elaborated.

Supporting Information

 
  • References

  • 1 Grauer A, König B. Eur. J. Org. Chem. 2009; 5099
    • 2a Gokhale AS, Seetharama S. Immunotherapy 2014; 6: 755
    • 2b Vagner J, Qu H, Hruby VJ. Curr. Opin. Chem. Biol. 2008; 12: 292
    • 2c Avan I, Hallb CD, Katritzky AR. Chem. Soc. Rev. 2014; 43: 3575
    • 2d Ung P, Winkler DA. J. Med. Chem. 2011; 54: 1111
    • 3a Derian CK, Maryanoff BE, Andrade-Gordon P, Zhang H.-C. Drug Dev. Res. 2003; 59: 355
    • 3b Fairlie DP. Aust. J. Chem. 2004; 57: 855
  • 4 For a general review, see: Guarna A, Trabocchi A. Peptidomimetics in Organic and Medicinal Chemistry . John Wiley & Sons; Chichester: 2014: 312
    • 5a Tamura SY, Shamblin BM, Brunck TK, Ripka WC. Bioorg. Med. Chem. Lett. 1997; 7: 1359
    • 5b Costanzo MJ, Almond HR. Jr, Hecker LR, Schott MR, Yabut SC, Zhang H.-C, Andrade-Gordon P, Corcoran TW, Giardino EC, Kauffman JA, Lewis JM, de Garavilla L, Haertlein BJ, Maryanoff BE. J. Med. Chem. 2005; 48: 1984
    • 6a McComsey DF, Hawkins MJ, Andrade-Gordon P, Addo MF, Oksenberg D, Maryanoff BE. Bioorg. Med. Chem. Lett. 1999; 9: 1423
    • 6b Yu Y, Ostresh JM, Houghten RA. J. Comb. Chem. 2002; 4: 484
    • 6c Mann E, Chana A, Sanchez-Sancho F, Puerta C, Garcia-Merino A, Herradon B. Adv. Synth. Catal. 2002; 344: 855
    • 6d Salgado A, Mann E, Sanchez-Sancho F, Herradon B. Heterocycles 2003; 60: 57
    • 7a Zabrocki J, Dunbar JB. Jr, Marshall KW, Toth MV, Marshall GR. J. Org. Chem. 1992; 57: 202
    • 7b Kohn WD, Zhang L. Tetrahedron Lett. 2001; 42: 4453
    • 7c Tornoe CW, Sanderson SJ, Mottram JC, Coombs GH, Meldal M. J. Comb. Chem. 2004; 6: 312
    • 8a Koopmanschap G, Ruijter E, Orru RV. A. Beilstein J. Org. Chem. 2014; 10: 544
    • 8b Cerminara I, Chiummiento L, Funicello M, Guarnaccio A, Lupattelli P. Pharmaceuticals 2012; 5: 297
    • 8c Biron E, Chatterjee J, Kessler H. Org. Lett. 2006; 8: 2417
  • 9 Biitseva AV, Rudenko IV, Hordiyenko OV, Jamart-Grégoire B, Arrault A. Eur. J. Org. Chem. 2012; 4387
    • 10a Holenz J, Karlström S (Astrazeneca AB) PCT Int. Appl. WO2011002409, 2011 ; Chem. Abstr. 2011, 154, 109655
    • 10b Kudrevich S, Brasseur N, La Madeleine C, Gilbert S, Van Lier JE. J. Med. Chem. 1997; 40: 3897
    • 10c (BASF SE) EP2371219, 2011 ; Chem. Abstr. 2011, 155, 503363
    • 10d Groll M, Berkers CR, Ploegh HL, Ovaa H. Structure 2006; 451
    • 11a Lagrange A, Andrean H (L’Oreal S. A.) US6451067, 2002 ; Chem. Abstr. 2000, 133, 79012
    • 11b Lagrange A, Andrean H (L’Oreal S. A.) US6635090, , 2003; Chem. Abstr. 2000, 133, 79010
    • 11c Lagrange A, Andrean H (L’Oreal S. A.) US6458168, 2002 ; Chem. Abstr. 2000, 133, 79011
    • 11d Andrean H, Lagrange A (L’Oreal) US6077320, 2000 ; Chem. Abstr. 1998, 129, 71930
  • 12 Brach PJ, Grammatica SJ, Ossanna OA, Weinberger L. J. Het. Chem. 1970; 7: 1403
  • 13 Genda Y, Tomita N, Ito M, Kano S. JP54119531, 1979 ; Chem. Abstr. 1980, 92, 95632
  • 14 Hordiyenko OV, Rudenko IV, Zamkova IA, Denisenko OV, Biitseva AV, Arrault A, Tolmachev AA. Synthesis 2013; 45: 3375
    • 15a Hordiyenko OV, Biitseva AV, Kornilov MYu, Brosse N, Hocquet A, Jamart-Grégoire B, Shishkin OV, Zubatyuk RI. Eur. J. Org. Chem. 2006; 2833
    • 15b Hordiyenko OV, Rudenko IV, Biitseva AV, Turov AV, Arrault A, Brosse N, Fabre O, Jamart-Grégoire B, Zubatyuk RI, Shishkin OV. Tetrahedron 2009; 65: 6218
  • 16 Gangadasu B, Narender P, Bharath Kumar S, Ravinder M, Ananda Rao B, Ramesh Ch, China Raju B, Jayathirtha Rao V. Tetrahedron 2006; 62: 8398
    • 17a Zhang X, Rodrigues J, Evans L, Hinkle B, Ballantyne L, Peña M. J. Org. Chem. 1997; 62: 6420
    • 17b Bigi F, Maggi R, Sartori G. Green Chem. 2000; 2: 140
  • 18 Sureshbabu VV Basavaprabhu, Synlett 2011; 1160
  • 19 Belvisi L, Gennari C, Mielgo A, Potenza D, Scolastico C. Eur. J. Org. Chem. 1999; 389
    • 20a Oh K, Guan Z. Chem. Commun. 2006; 3069
    • 20b Kishore R, Raghothama S, Balaram P. Biopolymers 1987; 26: 873
    • 21a Ressurreic AS. M, Bordessa A, Civera M, Belvisi L, Gennari C, Piarulli U. J. Org. Chem. 2008; 73: 652
    • 21b Nowick JS, Pairish M, Lee IQ, Holmes DL, Ziller JW. J. Am. Chem. Soc. 1997; 119: 5413
    • 21c Cierpicki T, Otlewski J. J. Biomol. NMR 2001; 21: 249
    • 22a Tucker TJ, Isaacs RC. A. The Development of Novel Noncovalent Thrombin Inhibitors. In Advances in Amino Acid Mimetics and Peptidomimetics. Vol. 2. Abell A. JAI Press Inc; Stamford (CT, USA): 1999: 53
    • 22b Wiley MR, Chirgadze NY, Clawson DK, Craft TJ, Gifford-Moore DS, Jones ND, Olkowski JL, Weir LC, Smith GF. Bioorg. Med. Chem. Lett. 1996; 6: 2387
    • 22c Lange UE. W, Baucke D, Hornberger W, Mack H, Seitz W, Höffken HW. Bioorg. Med. Chem. Lett. 2003; 13: 2029
    • 23a Peterlin-Mašič L, Jurca A, Marinko P, Jančar A, Kikelj D. Tetrahedron 2002; 58: 1557
    • 23b Peterlin-Mašič L, Mlinšek G, Šolmajer T, Trampuš-Bakija A, Stegnar M, Kikelj D. Bioorg. Med. Chem. Lett. 2003; 13: 789
    • 23c Kranjc A, Peterlin-Mašič L, Reven S, Mikic K, Preželj A, Stegnar M, Kikelj D. Eur. J. Med. Chem. 2005; 40: 782
  • 24 Devillers I, Arrault A, Olive G, Marchand-Brynaert J. Tetrahedron Lett. 2002; 43: 3161
  • 25 Gaccioli F, Franchi-Gazzola R, Lanfranchi M, Marchio L, Metta G, Pellinghelli MA, Tardito S, Tegoni M. J. Inorg. Biochem. 2005; 99: 1573
  • 26 Zefirov YuV. Crystallogr. Rep. 1997; 42: 865
  • 27 Burgi H.-B, Dunitz JD. Structure Correlation . Vol. 2. VCH; Weinheim: 1994: 741
  • 28 Dolomanov O, Bourhis L, Gildea R, Howard JA. K, Puschmann H. J. Appl. Crystallogr. 2009; 42: 339
  • 29 Sheldrick G. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008; 64: 112