A conformational mimetic approach for the synthesis of carbocyclic nucleosides as anti-HCV leads

ChemMedChem

Volumn 8, Issue 10, 2013, Pages 1673-1680

  Kasula, Mohan ^a   Balaraju, Tuniki ^a   Toyama, Massaki ^b   Thiyagarajan, Anandarajan ^a   Bal, Chandralata ^a   Baba, Masanori ^b   Sharon, Ashoke ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY   (India)

^b KAGOSHIMA UNIVERSITY   (Japan)

Author keywords

Antiviral agents; Carbocyclic nucleosides; Hepatitis C; Inhibitors; RNA dependent RNA polymerase

Indexed keywords

5 (4 AMINO 1H PYRAZOLO[3,4 D]PYRIMIDIN 1 YL) 3 (HYDROXYMETHYL)CYCLOPENT 3 ENE 1,2 DIOL; 5 (4 AMINO 3 BROMO 1H PYRAZOLO[3,4 D]PYRIMIDIN 1 YL) 3 (HYDROXYMETHYL)CYCLOPENT 3 ENE 1,2 DIOL; 5 (4 AMINO 3 CHLORO 1H PYRAZOLO[3,4 D]PYRIMIDIN 1 YL) 3 (HYDROXYMETHYL)CYCLOPENT 3 ENE 1,2 DIOL; 5 (4 AMINO 3 IODO 1H PYRAZOLO[3,4 D]PYRIMIDIN 1 YL) 3 (HYDROXYMETHYL)CYCLOPENT 3 ENE 1,2 DIOL; 6 AMINO 1H PYRAZOLO[3,4 D]PYRIMIDINE; ANTIVIRUS AGENT; CARBOCYCLIC NUCLEOSIDE; IODINE DERIVATIVE; PYRAZOLO[3,4 D]PYRIMIDINE DERIVATIVE; RNA DIRECTED RNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG; DNA DIRECTED RNA POLYMERASE; NUCLEOSIDE; PYRAZOLE DERIVATIVE; PYRAZOLO(3,4-D)PYRIMIDINE; PYRIMIDINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; BIOMIMETICS; COMPUTER AIDED DESIGN; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; HEPATITIS C VIRUS; HYDROPHOBICITY; MOLECULAR DOCKING; MOLECULAR DYNAMICS; PRIORITY JOURNAL; BINDING SITE; CHEMISTRY; CONFORMATION; DRUG EFFECTS; ENZYME ACTIVE SITE; HEPACIVIRUS; HUMAN; HYDROGEN BOND; METABOLISM; SYNTHESIS; VIRUS REPLICATION;

ANTIVIRAL AGENTS; BINDING SITES; CATALYTIC DOMAIN; DNA-DIRECTED RNA POLYMERASES; HEPACIVIRUS; HUMANS; HYDROGEN BONDING; MOLECULAR CONFORMATION; MOLECULAR DOCKING SIMULATION; NUCLEOSIDES; PYRAZOLES; PYRIMIDINES; VIRUS REPLICATION;

EID: 84884979852     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201300277     Document Type: Article

References (39)

1. D. Lavanchy, Clin. Microbiol. Infect. 2011, 17, 107-115.
2. M. T. Crimmins, Tetrahedron 1998, 54, 9229-9272.
3. X. F. Zhu, Nucleosides Nucleotides Nucleic Acids 2000, 19, 651-690;
4. M. Ferrero, V. Gotor, Chem. Rev. 2000, 100, 4319-4348.
5. A. B. Eldrup, M. Prhavc, J. Brooks, B. Bhat, T. P. Prakash, Q. Song, S. Bera, N. Bhat, P. Dande, P. D. Cook, J. Med. Chem. 2004, 47, 5284-5297;
6. A. Cho, O. L. Saunders, T. Butler, L. Zhang, J. Xu, J. E. Vela, J. Y. Feng, A. S. Ray, C. U. Kim, Bioorg. Med. Chem. Lett. 2012, 22, 2705-2707.
7. G. Wolfson, J. Chisholm, A. H. Tashjian, S. Fish, R. H. Abeles, J. Biol. Chem. 1986, 261, 4492-4498.
8. X. Liao, G. Butora, D. B. Olsen, S. S. Carroll, D. R. McMasters, J. F. Leone, M. Stahlhut, G. A. Doss, L. Yang, M. MacCoss, Tetrahedron Lett. 2008, 49, 4149-4152;
9. H. R. Lee, J. A. Kang, A. Y. Park, W. H. Kim, P. Chun, J. Kim, J. A. Kim, B. Lee, L. S. Jeong, H. R. Moon, Bull. Korean Chem. Soc. 2009, 30, 2043-2050;
10. H. Zhang, R. F. Schinazi, C. K. Chu, Bioorg. Med. Chem. 2006, 14, 8314-8322;
11. N. Hamon, J. P. Uttaro, C. Mathe, C. Perigaud, Bioorg. Chem. 2010, 38, 275-278.
12. H. J. Kim, A. Sharon, C. Bal, J. Wang, M. Allu, Z. Huang, M. G. Murray, L. Bassit, R. F. Schinazi, B. Korba, C. K. Chu, J. Med. Chem. 2009, 52, 206-213.
13. A. Thiyagarajan, M. T. A. Salim, T. Balaraju, C. Bal, M. Baba, A. Sharon, Bioorg. Med. Chem. Lett. 2012, 22, 7742-7747.
14. S. Sprang, R. Scheller, D. Rohrer, M. Sundaralingam, J. Am. Chem. Soc. 1978, 100, 2867-2872.
15. Y. V. Dobrynin, T. Bektemirov, T. Ivanova, E. Chekunova, O. Andzhaparidze, I. Korbukh, Y. B. Bulychev, N. Yakunina, M. Preobrazhenskaya, Pharm. Chem. J. 1980, 14, 279-284;
16. D. Smee, P. McKernan, L. D. Nord, R. Willis, C. Petrie, T. Riley, G. Revankar, R. Robins, R. Smith, Antimicrob. Agents Chemother. 1987, 31, 1535-1541;
17. L. M. Beauchamp, J. V. Tuttle, M. E. Rodriguez, M. L. Sznaidman, J. Med. Chem. 1996, 39, 949-956;
18. A. E. Rashad, A. H. Shamroukh, R. E. Abdel-Megeid, A. Mostafa, M. A. Ali, K. Banert, Nucleosides Nucleotides Nucleic Acids 2010, 29, 809-820.
19. V. E. Marquez, T. Ben-Kasus, J. J. Barchi, Jr., K. M. Green, M. C. Nicklaus, R. Agbaria, J. Am. Chem. Soc. 2004, 126, 543-549.
20. T. Balaraju, C. Bal, A. Sharon, Antiviral Res. 2012, A14.
21. R. T. Mosley, T. E. Edwards, E. Murakami, A. M. Lam, R. L. Grice, J. Du, M. J. Sofia, P. A. Furman, M. J. Otto, J. Virol. 2012, 86, 6503-6511.
22. Schrödinger LLC, New York, NY (USA), 2011.
23. G. Sun, J. H. Voigt, I. V. Filippov, V. E. Marquez, M. C. Nicklaus, J. Chem. Inf. Comput. Sci. 2004, 44, 1752-1762.
24. C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Delivery Rev. 2001, 46, 3-26.
25. W. L. Jorgensen, E. M. Duffy, Adv. Drug Delivery Rev. 2002, 54, 355-366.
26. J. H. Cho, D. L. Bernard, R. W. Sidwell, E. R. Kern, C. K. Chu, J. Med. Chem. 2006, 49, 1140-1148.
27. R. K. Robins, J. Am. Chem. Soc. 1956, 78, 784-790.
28. J. D. Anderson, N. K. Dalley, G. R. Revankar, R. K. Robins, J. Heterocycl. Chem. 1986, 23, 1869-1878.
29. H. B. Cottarn, G. R. Revankar, R. K. Robins, Nucleic Acids Res. 1983, 11, 871-882;
30. F. W. Lichtenthaler, E. Cuny, Chem. Ber. 1981, 114, 1610-1623.
31. F. Seela, A. M. Jawalekar, L. Sun, P. Leonard, Nucleosides Nucleotides Nucleic Acids 2005, 24, 1485-1505.
32. M. T. Salim, H. Aoyama, K. Sugita, K. Watashi, T. Wakita, T. Hamasaki, M. Okamoto, Y. Urata, Y. Hashimoto, M. Baba, Biochem. Biophys. Res. Commun. 2011, 415, 714-719.
33. K. Goto, K. Watashi, T. Murata, T. Hishiki, M. Hijikata, K. Shimotohno, Biochem. Biophys. Res. Commun. 2006, 343, 879-884.
34. M. P. Windisch, M. Frese, A. Kaul, M. Trippler, V. Lohmann, R. Bartenschlager, J. Virol. 2005, 79, 13778-13793.