Synthesis and HIV-1 integrase inhibitory activities of caffeoylglucosides.

作者: Sun Nam Kim , Jae Yeol Lee , Hyoung Ja Kim , Cha-Gyun Shin , Hokoon Park

DOI: 10.1016/S0960-894X(00)00355-3

关键词: Enzyme inhibitorChemical synthesisGlycosideIntegraseIC50EnzymeChemistryIn vitroLinkerStereochemistryBiochemistry

摘要: Abstract Caffeoylglucosides, which have a glucose ring as central linker, were synthesized from methyl d -glucosides, and their anti-HIV-1 activities tested. Among them, four dicaffeoylglucosides (IC50=29.1–35.1 μM), 6a , 6b 9b 10b showed HIV-1 integrase inhibitory activity potent l -chicoric acid.

参考文章(12)
H Sakai, M Kawamura, J Sakuragi, S Sakuragi, R Shibata, A Ishimoto, N Ono, S Ueda, A Adachi, Integration is essential for efficient gene expression of human immunodeficiency virus type 1. Journal of Virology. ,vol. 67, pp. 1169- 1174 ,(1993) , 10.1128/JVI.67.3.1169-1174.1993
B Taddeo, W A Haseltine, C M Farnet, Integrase mutants of human immunodeficiency virus type 1 with a specific defect in integration. Journal of Virology. ,vol. 68, pp. 8401- 8405 ,(1994) , 10.1128/JVI.68.12.8401-8405.1994
M Cordeiro, S Abdel-Malek, W E Robinson, S A Chow, Q Jia, W M Mitchell, M G Reinecke, Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase. Molecular Pharmacology. ,vol. 50, pp. 846- 855 ,(1996)
Peter J. King, Guoxiang Ma, Wenfang Miao, Qi Jia, Brenda R. McDougall, Manfred G. Reinecke, Chris Cornell, Jean Kuan, Tracey R. Kim, W. Edward Robinson, Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication. Journal of Medicinal Chemistry. ,vol. 42, pp. 497- 509 ,(1999) , 10.1021/JM9804735
Zhaiwei Lin, Nouri Neamati, He Zhao, Yoshimitsu Kiryu, Jim A. Turpin, Claudia Aberham, Klaus Strebel, Kurt Kohn, Myriam Witvrouw, Christophe Pannecouque, Zeger Debyser, Erik De Clercq, William G. Rice, Yves Pommier, Terrence R. Burke, Chicoric acid analogues as HIV-1 integrase inhibitors. Journal of Medicinal Chemistry. ,vol. 42, pp. 1401- 1414 ,(1999) , 10.1021/JM980531M
Nouri Neamati, Huixiao Hong, Abhijit Mazumder, Shaomeng Wang, Sanjay Sunder, Marc C. Nicklaus, George W. A. Milne, Bohumil Proksa, Yves Pommier, Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching. Journal of Medicinal Chemistry. ,vol. 40, pp. 942- 951 ,(1997) , 10.1021/JM960759E
Russell F. Lang, Telvin D. Ju, Gabor Kiss, Carl D. Hoff, Jeffrey C. Bryan, Gregory J. Kubas, Oxidative Addition of Thiols, Disulfides, Iodine, and Hydrogen Iodide to W(CO)3(PiPr3)2. Preparation of Stable 17-Electron Tungsten Thiolate Radicals from Complexes with Weak W-H Bonds Journal of the American Chemical Society. ,vol. 116, pp. 7917- 7918 ,(1994) , 10.1021/JA00096A067
Brenda McDougall, Peter J. King, Bor Wen Wu, Zdenek Hostomsky, Manfred G. Reinecke, W. Edward Robinson, Dicaffeoylquinic and Dicaffeoyltartaric Acids Are Selective Inhibitors of Human Immunodeficiency Virus Type 1 Integrase Antimicrobial Agents and Chemotherapy. ,vol. 42, pp. 140- 146 ,(1998) , 10.1128/AAC.42.1.140
A Engelman, G Englund, J M Orenstein, M A Martin, R Craigie, Multiple effects of mutations in human immunodeficiency virus type 1 integrase on viral replication. Journal of Virology. ,vol. 69, pp. 2729- 2736 ,(1995) , 10.1128/JVI.69.5.2729-2736.1995
Nouri Neamati, Huixiao Hong, Sanjay Sunder, George W. A. Milne, Yves Pommier, Potent Inhibitors of Human Immunodeficiency Virus Type 1 Integrase: Identification of a Novel Four-Point Pharmacophore and Tetracyclines as Novel Inhibitors Molecular Pharmacology. ,vol. 52, pp. 1041- 1055 ,(1997) , 10.1124/MOL.52.6.1041