Synthesis and HIV-1 inhibitory activities of dicaffeoyl and digalloyl esters of quinic acid derivatives

Current Medicinal Chemistry

Volumn 20, Issue 5, 2013, Pages 724-733

  Junior, C O R ^a   Verde, S C ^b   Rezende, C A M ^a   Caneschi, W ^a   Couri, M R C ^a   McDougall, B R ^b   Robinson, W E ^b   De Almeida, M V ^a  

^a FEDERAL UNIVERSITY OF JUIZ DE FORA   (Brazil)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Anti HIV agents; Catechol; Cyclitol; Dicaffeoyl; Digalloyl; Esters; HIV 1; Integrase inhibitor; Quinic acid; Second generation inhibitor

Indexed keywords

1,2 O CYCLOHEXYLIDENE 3,5 DI O ( 3',4' DI O ACETYL)CAFFEOYL 1,2,3,5 CYCLOHEXANETETROL; 1,2 O CYCLOHEXYLIDENE 3,5 DI O ( 3',4',5' TRI O ACETYL)GALLOYL 1,2,3,5 CYCLOHEXANETETROL; 1,2 O CYCLOHEXYLIDINE 3,5 DI O ( 3',4' DI O ACETYL)CAFFEOYL 1,2,3,5 CYCLOHEXANETETROL; 3,5 DI O CAFFEOYL 1,2,3,5 CYCLOHEXANETETROL; 3,5 DI O GALLOYL 1,2,3,5 CYCLOHEXANETETROL; ALKENE DERIVATIVE; ANTIRETROVIRUS AGENT; ANTIVIRUS AGENT; CAFFEIC ACID; CAFFEIC ACID DERIVATIVE; CYCLOHEXYLIDENE; DICAFFEOYLTARTARIC ACID; ELVITEGRAVIR; GALLIC ACID; INTEGRASE INHIBITOR; ISOCHLOROGENIC ACID; QUINIC ACID; QUINIC ACID DERIVATIVE; RALTEGRAVIR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; BENZYLATION; BIOASSAY; CELL CULTURE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACETYLATION; DRUG INHIBITION; DRUG POTENCY; DRUG SYNTHESIS; EX VIVO STUDY; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; IN VITRO STUDY; MOLECULE; NONHUMAN; NUCLEOTIDE SEQUENCE; RNA PROCESSING; STRUCTURE ACTIVITY RELATION; VIRUS DNA CELL DNA INTERACTION; VIRUS REPLICATION; VIRUS STRAIN;

EID: 84877962220     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986713804999349     Document Type: Article

References (38)

1. Charvat, T. T.; Lee, D. J.; Robinson Jr., W. E.; Chamberlin, A. R. Design, synthesis, and biological evaluation of chicoric acid analogs as inhibitors of HIV-1 integrase. Bioorg. Med. Chem. 2006, 14, 4552-4567
2. Lee, J. Y.; Yoon, K. J.; Lee, Y. S. Catechol-substituted L-chicoric acid analogues as HIV integrase inhibitors. Bioorg. Med. Chem. Lett. 2003, 13, 4331-4334
3. Lin, Z.; Neamati, N.; Zhao, H.; Kiryu, Y.; Turpin, J. A.; Aberham, C.; Strebel, K.; Kohn, K.; Witvrouw, M.; Pannecouque, C.; Debyser, Z.; De Clercq, E.; Rice, W. G.; Pommier, Y.; Burke Jr., T. R. Chicoric acid analogues as HIV-1 integrase inhibitors. J. Med. Chem. 1999, 42, 1401-1414
4. King, P. J.; Ma, G.; Miao, W.; Jia, Q.; McDougall, B. R.; Reinecke, M. G.; Cornell, C.; Kuan, J.; Kim, T. R.; Robinson Jr., W. E. Structure-Activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication. J. Med. Chem. 1999, 42, 497-509
5. Kim, S. N.; Lee, J. Y.; Kim, H. J.; Shin, C.; Parka, H.; Lee, Y. S. Synthesis and HIV-1 integrase inhibitory activities of caffeoylglucosides. Bioorg. Med. Chem. Lett. 2000, 10, 1879-1882
6. Hwang, D. J.; Kim, S. N.; Choib, J. H.; Lee, Y. S. Dicaffeoyl-or digalloyl pyrrolidine and furan derivatives as HIV integrase inhibitors. Bioorg. Med. Chem. 2001, 9, 1429-1437
7. Xu, Y.; Zhao, G.; Shin, C.; Zang, H.; Leec, C.; Leed, Y. S. Caffeoyl naphthalenesulfonamide derivatives as HIV integrase inhibitors. Bioorg. Med. Chem. 2003, 11, 3589-3593
8. Kim, H. J.; Woo, E.; Shin, C.; Park, H. A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against Human Immunodeficiency Virus-1 (HIV-1) integrase. J. Nat. Prod. 1998, 61, 145-148
9. Ahn, M. J.; Kim, C. Y.; Lee, J. S.; Kim, T. G.; Kim, S. H.; Lee, C. K.; Lee, B. B.; Shin, C. G.; Huh, H.; Kim, J. Inhibition of HIV-1 integrase by galloyl glucoses from Terminalia chebula and flavonol glycoside gallates from Euphorbia pekinensis. Planta Med. 2002, 68, 457-459
10. Pommier, Y.; Marchand, C.; Neamati, N. Retroviral integrase inhibitors year 2000: update and perspectives. Antivir. Res. 2000, 47, 139-148
11. Neamati, N.; Hong, H.; Owen, J. M.; Sunder, S.; Winslow, H. E.; Christensen, J. L.; Zhao, H.; Burke, T. R. J.; Milne, G. W. A.; Pommier, Y. Salicylhydrazine-containing inhibitors of HIV-1 integrase: implication for a selective chelation in the integrase active site. J. Med. Chem. 1998, 41, 3202-3209
12. Barco, A.; Benetti, S.; Risi, D. C.; Marchetti, P.; Pollini, G. P.; Zanirato, V. D-(-)-Quinic acid: a chiron store for natural product synthesis. Tetrahedron: Asymmetry 1997, 8, 3515-3545
13. Shing, T. K. M.; Tang, Y. A new approach to pseudo-sugars from (-)-quinic acid: facile syntheses of pseudo-D-mannopyranose and pseudo-Dfructopyranose. J. Chem. Soc. Communs. 1990, 748-749
14. Shing, T. K. M.; Cui, Y.; Tang, Y. Facile syntheses of pseudo-Dglucopyranose and pseudo-D-mannopyranose. J. Chem. Soc. Communs. 1991, 756-757
15. Herrera, L.; Feist, H.; Michalik, M.; Quincoces, J.; Peseke, K. Synthesis of anellated carbasugars from (-)-quinic acid. Carbohydr. Res. 2003, 338, 293-298
16. Carballido, M.; Castedo, L.; Gonzalez, C. Synthesis of carba-sugars from (-)-quinic acid. Tetrahedron Lett. 2001, 42, 3973-3976
17. Baptistella, L. H. B.; Cerchiaro, G. Studies for the transformation of carbocycles into carbohydrates: approach toward the synthesis of higher sugar derivatives. Carbohydr. Res. 2004, 339, 665-671
18. Sefkow, M. First efficient synthesis of chlorogenic acid. Eur. J. Org. Chem. 2001, 1137-1141
19. Gazit, A.; Yaish, P.; Gilon, C.; Levitzki, A. Tyrphostins I: synthesis and biological activity of protein tyrosine kinase inhibitors. J. Med. Chem. 1989, 32, 2344-2352
20. Belin, F.; Barthelemy, P.; Ruiz, K.; Lacombe, J. M.; Pucci, B. Synthetic gallic acid derivatives as models for a comprehensive study of antioxidant activity. Helv. Chim. Acta, 2003, 86, 247-265
21. Ren, Y.; Himmeldirk, K.; Chen, X. Synthesis and structure-Activity relationship study of antidiabetic penta-O-galloyl-D-glucopyranose and its analogues. J. Med. Chem. 2006, 49, 2829-2837
22. Castellanos, J.; Cleophax, J.; Colas, C.; Gero, S. D.; Leboul, J.; Mercier, D.; Olesker, A.; Rolland, A.; Quiclet-Sire, B.; Sepulchre, A. Synthesis of aminocyclitols from l-quinic acid. Carbohydr. Res. 1980, 82, 283-301
23. Murali, C.; Shashidhar, M. S.; Gopinath, C. S. Hydroxyl group deprotection reactions with Pd(OH)2/C: a convenient alternative to hydrogenolysis of benzyl ethers and acid hydrolysis of ketals.Tetrahedron 2007, 63, 4149-4155
24. Mercier, D.; Leboul, J.; Cleophax, J.; Gero, S. D. Some ring-opening reactions of a diepoxide derived from (-)-quinic acid. Carbohydr. Res. 1971, 20, 299-304
25. Robinson Jr., W. E; Cordeiro, M. L.; Abdel-Malek, S.; Jia, Q.; Chow; S. A.; Reinecke, M. G.; Mitchell, W. M. Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase. Mol. Pharmacol. 1996, 50, 846-855
26. Reinke, R. A.; King, P. J.; Victoria, J. G.; McDougall, B. R.; Ma, G.; Mao, Y.; Reincecke, M. G.; Robinson Jr., W. E. Dicaffeoyltartaric acid analogues inhibit human immunodeficiency virus type 1 (HIV-1) integrase and HIV-1 replication at nontoxic concentrations. J. Med. Chem. 2002, 45, 3669-3683
27. Jiang, F.; Chen, W.; Yi, K.; Wu, Z.; Si, Y.; Han, W.; Zhao, Y. The evaluation of catechins that contain a galloyl moiety as potential HIV-1 integrase inhibitors. Clin. Immunol. 2010, 137, 347-356
28. Sato, M.; Kawakami, H.; Motomura, T.; Aramaki, H.; Matsuda, T.; Yamashita, M.; Ito, Y.; Matsuzaki, Y; Yamataka, K.; Ikeda, S.; Shinkai, H. Quinolone carboxylic acids as a novel monoketo acid class of human immunodeficiency virus type 1 integrase inhibitors. J. Med. Chem. 2009, 52, 4869-4882
29. Sotriffer, C. A.; Ni, H.; McCammon, A. Active site binding modes of HIV-1 integrase inhibitors. J. Med. Chem. 2000, 43, 4109-4117
30. Hare, S.; Gupta, S. S.; Valkov, E.; Engelman, A.; Cherepanov, P. Retroviral intasome assembly and inhibition of DNA strand transfer. Nature 2010, 464, 232-237
31. Chow, S. A. In vitro assays for activities of retroviral integrase. Methods. 1997, 12, 306-317
32. Marchand, C.; Johnson, A. A.; Karki, R. G.; Pais, G. C. G. Zhang, X.; Cowansage, K.; Patel, T. A.; Nicklaus, M. C.; Burke, Jr., T. R.; Pommier, Y. Metal-dependent inhibition of HIV-1 integrase by -diketo acids and resistance of the soluble double-mutant (F185K/C280S). Mol. Pharm. 2003, 64, 600-609
33. Engleman, A.; Craigie, R. Efficient magnesium-dependent human immunodeficiency virus type 1 integrase activity. J. Virol. 1995, 69, 5908-5911
34. Chow, S. A.; Vincent, K. A.; Ellison, V.; Brown, P. O. Reversal of integration and DNA splicing mediated by integrase of human immunodeficiency virus. Science. 1992, 255, 723-726
35. King, P. J.; Robinson Jr., W. E. Resistance to the anti-human immunodeficiency virus type 1 compound L-chicoric acid results from a single mutation at amino acid 140 of integrase. J. Virol. 1998, 72, 8420-8424
36. O'Doherty, U.; Swiggard, W. J.; Jeyakumar, D.; McGain, D.; Malim, M. H. A sensitive, quantitative assay for human immunodeficiency virus type 1 integration. J. Virol. 2002, 10942-10950
37. Lee, D. J.; Robinson Jr., W. E. Human immunodeficiency virus type 1 (HIV-1) integrase: Resistance to diketo acid integrase inhibitors impairs HIV-1 replication and integration and confers cross-resistance to L-chicoric acid. Antimicrob. Agents Chemother. 2004, 50, 5835-5847
38. Montefiori, D. C.; Robinson Jr., W. E.; Schuffman, S. S.; Mitchell, W. M. Evaluation of antiviral drugs and neutralizing antibodies against human immunodeficiency virus by a rapid and sensitive microtiter infection assay. J. Clin. Microbiol. 1988, 26, 231-235