Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of l-chicoric acid, as new HIV-1 integrase inhibitors

European Journal of Medicinal Chemistry

Volumn 42, Issue 10, 2007, Pages 1309-1315

  Lee, Seung Uk ^a   Shin, Cha Gyun ^b   Lee, Chong Kyo ^c   Lee, Yong Sup ^d  

^a Korea Institute of Science and Technology   (South Korea)

^b Chung Ang University   (South Korea)

^c Korea Research Institute of Chemical Technology   (South Korea)

^d Kyung Hee University   (South Korea)

Author keywords

Caffeoylamino acid; Caffeoylglycolic acid; Human immunodeficiency virus; Integrase inhibitor; l Chicoric acid

Indexed keywords

2 [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO] 3 (4 HYDROXY PHENYL)PHENYL PROPIONIC ACID METHYL ESTER; 2 [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO] 3 (4 HYDROXY PHENYL)PROPIONIC ACID; 2 [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO] 3 PHENYL PROPIONIC ACID; 2 [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO] 4 METHYL PENTANOIC ACID; 2 [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO]PENTANOIC ACID METHYL ESTER; 2 [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO]PHENYL PROPIONIC ACID METHYL ESTER; 2 [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO]PROPIONIC ACID; 2 [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO]PROPIONIC ACID METHYL ESTER; 3 (3,4 DIHYDROXY PHENYL) 2 [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO]PROPIONIC ACID; 3 (3,4 DIHYDROXY PHENYL) 2 [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO]PROPIONIC ACID METHYL ESTER; 3 (3,4 DIHYDROXY PHENYL)ACRYLIC ACID 1 CARBOXY ETHYL ESTER; 3 (3,4 DIHYDROXY PHENYL)ACRYLIC ACID CARBOXYMETHYL ESTER; 3 (3,4 DIMETHOXY PHENYL)ACRYLIC ACID CARBOXYMETHYL ESTER; 3 (3,4 DIMETHOXY PHENYL)ACRYLIC ACID METHOXYCARBONYLMETHYL ESTER; 3 (3,4 HYDROXY PHENYL)ACRYLIC ACID 1 METHOXYCARBONYL ETHYL ESTER; 3 (3,4 HYDROXY PHENYL)ACRYLIC ACID METHOXYCARBONYLMETHYL ESTER; 3 (4 HYDROXY 3 METHOXY PHENYL)ACRYLIC ACID CARBOXYMETHYL ESTER; 3 (4 HYDROXY 3 METHOXY PHENYL)ACRYLIC ACID METHOXYCARBONYLMETHYL ESTER; [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO]ACETIC ACID; [3 (3,4 DIHYDROXY PHENYL)ACRYLOYLAMINO]ACETIC ACID METHYL ESTER; CICHORIC ACID; INTEGRASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CATALYSIS; CONTROLLED STUDY; DNA SYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN;

AMINO ACIDS; CAFFEIC ACIDS; CATECHOLS; DRUG DESIGN; HIV INTEGRASE INHIBITORS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; SUCCINATES;

EID: 35248875223     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2007.02.016     Document Type: Article

References (19)

1. Barre-Sinoussi F., Chermann J.C., Rey F., Nugeyre M.T., Chemaret S., Gruest J., Dauguet C., Axler-Blin C., Byun-Vezinet F., Rouzioux C., Rozenbaum W., and Montagnier L. Science 220 (1983) 868-871
2. Zhang X., Neamati N., Lee Y.K., Orr A., Brown R.D., Whitaker N., Pommier Jr. Y., and Burke T.R. Bioorg. Med. Chem. 9 (2001) 1649-1657
3. Robinson Jr. W.E., Reinecke M.G., Abdel-Malek S., Jia Q., and Chow S.A. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 6326-6331
4. Robinson Jr. W.E., Codeiro M., Abdel-Malek S., Jia Q., Chow S.A., Reinecke M.G., and Mitchell W.M. Mol. Pharmacol. 50 (1996) 846-855
5. McDougall B.R., King P.J., Wu B.W., Hostomsk Z., Reinecke M.G., and Robinson Jr. W.E. Antimicrob. Agents Chemother. 42 (1998) 140-146
6. Neamati N., Hong H., Mazumder A., Wang S., Sunder S., Nicklaus M.C., Milne G.W.A., Proska B., and Pommier Y. J. Med. Chem. 40 (1997) 942-951
7. Lamidey A.M., Fernon L., Pouysegu L., Delattre C., and Quideau S. Helv. Chim. Acta 85 (2002) 2328-2334
8. Zhao H., and Burke Jr. T.R. Synth. Commun. 28 (1998) 737
9. King P.J., Ma G., Miao W., Jia Q., McDougall B.R., Reinecke M.G., Cornell C., Kuan J., Kim T.R., and Robinson Jr. W.E. J. Med. Chem. 42 (1999) 497-509
10. 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., and Burke Jr. T.R. J. Med. Chem. 42 (1999) 1401-1414
11. Charvat T.T., Lee D.J., Robinson W.E., and Chamberlin A.R. Bioorg. Med. Chem. 14 (2006) 4552-4567
12. Kim S.N., Lee J.Y., Kim H.J., Shin C.-G., Park H., and Lee Y.S. Bioorg. Med. Chem. Lett. 10 (2000) 1879-1882
13. Hwang D.J., Kim S.N., Choi J.H., and Lee Y.S. Bioorg. Med. Chem. 9 (2001) 1429-1437
14. Lee Y.J., Yoon K.J., and Lee Y.S. Bioorg. Med. Chem. Lett. 13 (2003) 4331-4334
15. Minguez J.M., Kim S.-Y., Giuliano K.A., Balachandran R., Madiraju C., Day B.W., and Curran D.P. Bioorg. Med. Chem. 11 (2003) 3335-3357
16. Parrish J.P., Dueno E.E., Kim S.-I., and Jung K.W. Synth. Commun. 30 (2000) 2687-2700
17. Fisher J.W., and Trinkle K.L. Tetrahedron Lett. 35 (1994) 2505-2508
18. For HIV-1 integrase inhibition assay procedures of compounds: See. Oh J.-W., and Shin C.-G. Mol. Cells 6 (1996) 96-100
19. For cell based anti-HIV and cytotoxicity assay procedures: see Ref. [13].