Synthesis and biological activity of benzo-fused 7-deazaadenosine analogues. 5- and 6-substituted 4-amino- or 4-alkylpyrimido[4,5-b]indole ribonucleosides

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 17, 2013, Pages 5362-5372

  Tichý, Michal ^a   Pohl, Radek ^a   Tloušt'Ová, Eva ^a   Weber, Jan ^a   Bahador, Gina ^b   Lee, Yu Jen ^b   Hocek, Michal ^a,c  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b GILEAD SCIENCES   (United States)

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Anti dengue virus activity; Pyrimido 4,5 b indoles; Suzuki and Stille cross coupling

Indexed keywords

4 (N METHYLAMINO) 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 (N,N DIMETHYLAMINO) 9 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) PYRIMIDO[4,5 B]INDOLE; 4 (N,N DIMETHYLAMINO) 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 ALKYLPYRIMIDO[4,5 B]INDOLE RIBONUCLEOSIDE DERIVATIVE; 4 AMINO 5 BUTYL 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 5 CHLORO 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 5 FURAN 2 YL 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 5 PHENYL 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 5 THIOPHEN 3 YL 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 6 BENZOFURAN 2 YL 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 6 CHLORO 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 6 FURAN 2 YL 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 6 FURAN 3 YL 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 6 PHENYL 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 6 THIOPHEN 2 YL 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 6 THIOPHEN 3 YL 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINO 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4 AMINOPYRIMIDO[4,5 B]INDOLE RIBONUCLEOSIDE DERIVATIVE; 4 CYCLOPROPYL 9 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) PYRIMIDO[4,5 B]INDOLE; 4 METHYL 9 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL) PYRIMIDO[4,5 B]INDOLE; 4 METHYL 9 BETA DEXTRO RIBOFURANOSYL PYRIMIDO[4,5 B]INDOLE; 4,5 DICHLORO 9 (2,3,5 TRI O BENZOYL BETA DEXTRO RIBOFURANOSYL)PYRIMIDO[4,5 B]INDOLE; 4,5 DICHLORO 9H PYRIMIDO[4,5 B]INDOLE; 5 CHLORO 3H PYRIMIDO[4,5 B]INDOL 4(9H) ONE; 7 DEAZAADENOSINE DERIVATIVE; ADENOSINE DERIVATIVE; BORONIC ACID DERIVATIVE; ETHYL 2 AMINO 4 CHLORO 1H INDOLE 3 CARBOXYLATE; RIBONUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CANCER CELL CULTURE; CATALYSIS; CELL VIABILITY; CONTROLLED STUDY; DENGUE VIRUS; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE SPECTROSCOPY; HEPATITIS C VIRUS; HUMAN; HUMAN CELL; IC 50; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; STILLE REACTION; SUBSTITUTION REACTION; SUZUKI REACTION; ULTRAVIOLET SPECTROSCOPY;

DENGUE VIRUS; DENGUE VIRUS GROUP; HEPATITIS C VIRUS; PHOS;

ANTI-DENGUE VIRUS ACTIVITY; NUCLEOSIDES; PYRIMIDO[4,5-B]INDOLES; SUZUKI AND STILLE CROSS-COUPLING;

ADENOSINE; ANTIVIRAL AGENTS; CATALYSIS; CELL LINE, TUMOR; CELL SURVIVAL; DENGUE VIRUS; HELA CELLS; HEP G2 CELLS; HEPACIVIRUS; HL-60 CELLS; HUMANS; INDOLES; PALLADIUM; RIBONUCLEOSIDES;

EID: 84881375637     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.06.011     Document Type: Article

References (28)

1. P. Nauš, R. Pohl, I. Votruba, P. Džubák, M. Hajdúch, R. Ameral, G. Birkuš, T. Wang, A.S. Ray, R. Mackman, T. Cihlar, and M. Hocek J. Med. Chem. 53 2010 460
2. A. Bourderioux, P. Nauš, P. Perlíková, R. Pohl, I. Pichová, I. Votruba, P. Džubák, P. Konečný, M. Hajdúch, K.M. Stray, T. Wang, A.S. Ray, J.Y. Feng, G. Birkus, T. Cihlar, and M. Hocek J. Med. Chem. 54 2011 5498
3. P. Nauš, P. Perlíková, R. Pohl, and M. Hocek Collect. Czech. Chem. Commun. 76 2011 957
4. P. Spáčilová, P. Nauš, R. Pohl, I. Votruba, J. Snášel, H. Zábranská, I. Pichová, R. Ameral, G. Birkuš, T. Cihlář, and M. Hocek ChemMedChem 5 2010 1386
5. P. Perlíková, R. Pohl, I. Votruba, R. Shih, G. Birkuš, T. Cihlář, and M. Hocek Bioorg. Med. Chem. 19 2011 229
6. R. Wu, E.D. Smidansky, H.S. Oh, R. Takhampunya, R. Padmanabhan, C.E. Cameron, and B.R. Peterson J. Med. Chem. 53 2010 7958
7. Z. Yin, Y.-L. Chen, W. Schul, Q.-Y. Wang, F. Gu, J. Duraiswamy, R.R. Kondreddi, P. Niyomrattanakit, S.B. Lakshminarayana, A. Goh, H.Y. Xu, W. Liu, B. Liu, J.Y.H. Lim, C.Y. Ng, M. Qing, C.C. Lim, A. Yip, G. Wang, W.L. Chan, H.P. Tan, K. Lin, B. Zhang, G. Zou, K.A. Bernard, C. Garrett, K. Beltz, M. Dong, M. Weaver, H. He, A. Pichota, V. Dartois, T.H. Keller, and P.-Y. Shi PNAS 106 2009 20435
8. M. Tichý, R. Pohl, H.Y. Xu, Y.-L. Chen, F. Yokokawa, P.-Y. Shi, and M. Hocek Bioorg. Med. Chem. 20 2012 6123
9. P.M. Traxler, P. Furet, H. Mett, E. Buchdunger, T. Meyer, and N. Lydon J. Med. Chem. 39 1996 2285
10. H.D.H. Showalter, A.J. Bridges, H. Zhou, A.D. Sercel, A. McMichael, and D.W. Fry J. Med. Chem. 42 1999 5464
11. A. Gangjee, N. Zaware, S. Raghavan, B.C. Disch, J.E. Thorpe, A. Bastian, and M.A. Ihnat Bioorg. Med. Chem. 21 2013 1857
12. A. Gangjee, N. Zaware, R.K.V. Devambatla, S. Raghavan, C.D. Westbrook, N.F. Dybdal-Hargreaves, E. Hamel, and S.L. Mooberry Bioorg. Med. Chem. 21 2013 891
13. Y.-M. Zhang, T. Razler, and P.F. Jackson Tetrahedron Lett. 43 2002 8235
14. J.A. Hyatt, and J.S. Swenton J. Org. Chem. 37 1972 3216
15. C. Hubschwerlen, P. Pfliger, J.-L. Specklin, K. Gubernator, H. Gmunder, P. Angehrn, and I. Kompis J. Med. Chem. 35 1992 1385
16. B. Venugopalan, P.D. Desai, and N.J. de Souza J. Heterocycl. Chem. 25 1988 1633
17. A. Okamoto, K. Tanaka, T. Fukuta, and I. Saito J. Am. Chem. Soc. 125 2003 9296
18. A. Okamoto, K. Tanaka, and I. Saito J. Am. Chem. Soc. 125 2003 5066
19. A. Okamoto, T. Kamei, and I. Saito J. Am. Chem. Soc. 128 2006 658
20. A. Okamoto, K. Tanaka, and I. Saito J. Am. Chem. Soc. 126 2004 9458
21. A. Okamoto, K. Tanaka, K. Nishiza, and I. Saito Bioorg. Med. Chem. 12 2004 5875
22. Review on cross-coupling reactions of nucleosides: L.A. Agrofoglio, I. Gillaizeau, and Y. Saito Chem. Rev. 103 2003 1875
23. M. Štefko, L. Slavětínská, B. Klepetářová, and M. Hocek J. Org. Chem. 2010 442
24. J.F. Gerster, B. Carpenter, R.K. Robins, and L.B. Townsend J. Med. Chem. 10 1967 326
25. D.A. Scudiero, R.H. Shoemaker, K.D. Paull, A. Monks, S. Tierney, T.H. Nofziger, M.J. Currens, D. Seniff, and M.R. Boyd Cancer Res. 48 1988 4827
26. J. Bárta, L. Slavětínská, B. Klepetářová, and M. Hocek Eur. J. Org. Chem. 2010 5432
27. A. Gangjee, N. Zaware, S. Raghavan, M. Ihnat, S. Shenoy, and R.L. Kisliuk J. Med. Chem. 53 2010 1563
28. M. Kuchař, R. Pohl, B. Klepetářová, I. Votruba, and M. Hocek Org. Biomol. Chem. 6 2008 2377