Design, synthesis and biological evaluation of indolizine derivatives as HIV-1 VIF-ElonginC interaction inhibitors

Molecular Diversity

Volumn 17, Issue 2, 2013, Pages 221-243

  Huang, Wenlin ^a   Zuo, Tao ^b   Jin, Hongwei ^a   Liu, Zhenming ^a   Yang, Zhenjun ^a   Yu, Xianghui ^b   Zhang, Liangren ^a   Zhang, Lihe ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b JILIN UNIVERSITY   (China)

Author keywords

Anti HIV 1; Indolizine derivatives; Structure activity relationship; VEC 5; VIF ElonginC interaction inhibition

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; APOLIPOPROTEIN B MESSENGER RNA EDITING ENZYME CATALYTIC POLYPEPTIDE 3G; ETHYL 3 (BENZYLCARBAMOYL) 7 PICOLINOYLINDOLIZINE 1 CARBOXYLATE; ETHYL 3 BENZOYL 7 (1 PHENYLETHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 3 BENZOYL 7 (2 METHOXY 2 OXO 1 PHENYLETHYLCARBAMOYL)INDOLIZINE 1 CARBOXALATE; ETHYL 3 BENZOYL 7 (2,3 DIHYDRO 1H INDEN 2YLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 3 BENZOYL 7 (3 FLUOROBENZYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 3 BENZOYL 7 (BENZYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 3 BENZOYL 7 (FURAN 2 YLMETHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 3 BENZOYL 7 (NAPHTHALEN 2 YLMETHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 3 BENZOYL 7 (PYRIDIN 2YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 3 BENZOYL 7 (PYRIDIN 3 YLMETHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 7 (2 CHLOROISONICOTINOYL) 3 (PYRIDIN 2 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 7 (2 CHLOROISONICOTINOYL) 3 (PYRIDIN 3 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 7 (3 METHOXYBENZOYL) 3 (PYRIDIN 2 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 7 (3 METHOXYBENZOYL) 3 (PYRIDIN 3 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 7 (FURAN 2 CARBONYL) 3 (PYRIDIN 2 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 7 (FURAN 2 CARBONYL) 3 (PYRIDIN 3 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 7 [BENZO(DEXTRO)(1,3)DIOXOL 5 YLMETHYLCARBAMOYL] 3 BENZOYLINDOLIZINE 1 CARBOXYLATE; ETHYL 7 PICOLINOYL 3 (PYRIDIN 2 YLMETHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 7 PICOLINOYL 3 (PYRIDIN 3 YLMETHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 8 (FURAN 2 CARBONYL) 3 (PYRIDIN 2 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 8 (FURAN 2 CARBONYL) 3 (PYRIDIN 3 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 8 BENZOYL 3 (PYRIDIN 2 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 8 BENZOYL 3 (PYRIDIN 3 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 8 PICOLINOYL 3 (PYRIDIN 2 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; ETHYL 8 PICOLINOYL 3 (PYRIDIN 3 YL METHYLCARBAMOYL)INDOLIZINE 1 CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIRAL INFECTIVITY FACTOR; VIRUS PROTEIN;

ANTIVIRAL ACTIVITY; ARTICLE; CHIRALITY; COMPETITIVE INHIBITION; CYTOTOXICITY; DRUG DESIGN; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 1 INFECTION; HYDROGEN BOND; HYDROPHOBICITY; MELTING POINT; MOLECULAR DOCKING; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN PROTEIN INTERACTION; PROTEIN TARGETING; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION;

ANTI-HIV AGENTS; BACTERIAL PROTEINS; CELL LINE; CELL SURVIVAL; CULLIN PROTEINS; CYTIDINE DEAMINASE; DRUG DESIGN; EMBRYONIC STEM CELLS; GENES, REPORTER; HEK293 CELLS; HIV-1; HOST-PATHOGEN INTERACTIONS; HUMANS; INDOLIZINES; INHIBITORY CONCENTRATION 50; LUMINESCENT PROTEINS; MOLECULAR DOCKING SIMULATION; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSCRIPTION FACTORS; TRANSFECTION; VIF GENE PRODUCTS, HUMAN IMMUNODEFICIENCY VIRUS;

EID: 84880699191     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-013-9424-3     Document Type: Article

References (27)

1. U.S. Food and Drug Administration (2012) Drugs used in the treatment of HIV infection. Silver Spring, MD. http://www.fda.gov/ForConsumers/ByAudience/ ForPatientAdvocates/HIVandAIDSActivities/ucm118915.htm. Accessed 17 August 2012
2. D'Aquila RT, Schapiro JM, Brun-Vezinet F, Clotet B, Conway B, Demeter LM, Grant RM, Johnson VA, Kuritzkes DR, Loveday C, Shafer RW, Richman DD (2003) Drug resistance mutations in HIV-1. Topics in HIV medicine. The international AIDS society, USA 11:92-96
3. Richman DD, Morton SC, Wrin T, Hellmann N, Berry S, Shapiro MF, Bozzette SA (2004) The prevalence of antiretroviral drug resistance in the United States. AIDS 18:1393-1401
4. Ross L, Lim ML, Liao Q, Wine B, Rodriguez AE, Weinberg W, Shaefer M (2007) Prevalence of antiretroviral drug resistance and resistance-associated mutations in antiretroviral therapy-naive HIV-infected individuals from 40 United States cities. HIV Clin Trials 8:1-8. doi: 10.1310/hct0801-1
5. Adamson CS, Freed EO (2010) Novel approaches to inhibiting HIV-1 replication. Antivir Res 85:119-141. doi: 10.1016/j.antiviral.2009.09.009
6. Greene WC, Debyser Z, Ikeda Y, Freed EO, Stephens E, Yonemoto W, Buckheit RW, Este JA, Cihlar T (2008) Novel targets for HIV therapy. Antivir Res 80:251-265. doi: 10.1016/j.antiviral.2008.08.003
7. Harris RS, Bishop KN, Sheehy AM, Craig HM, Petersen-Mahrt SK, Watt IN, Neuberger MS, Malim MH (2003) DNA deamination mediates innate immunity to retroviral infection. Cell 113:803-809
8. Lecossier D, Bouchonnet F, Clavel F, Hance AJ (2003) Hypermutation of HIV-1 DNA in the absence of the Vif protein. Science 300:1112. doi: 10.1126/science.1083338
9. Mangeat B, Turelli P, Caron G, Friedli M, Perrin L, Trono D (2003) Broad antiretroviral defence by human APOBEC3G through lethal editing of nascent reverse transcripts. Nature 424:99-103. doi: 10.1038/nature01709
10. Izumi T, Shirakawa K, Takaori-Kondo A (2008) Cytidine deaminases as a weapon against retroviruses and a new target for antiviral therapy. Mini Rev Med Chem 8:231-238
11. Takumi K, Katsumi M, Shuhei K, Masaki M, Daisuke K, Ronald CC, Joan WC, Keiichil N (2004) VHL-box and SOCS-box domains determine binding specificity for Cul2-Rbx1 and Cul5-Rbx2 modules of ubiquitin ligases. Gene Dev 18:3055-3065. doi: 10.1101/gad.1252404
12. Mehle A, Thomas ER, Rajendran KS, Gabuzda D (2006) A zinc-binding region in Vif binds Cul5 and determines cullin selection. J Biol Chem 281:17259-17265. doi: 10.1074/jbc.M602413200
13. Fujita M, Akari H, Sakurai A, Yoshida A, Chiba T, Tanaka K, Strebel K, Adachi A (2004) Expression of HIV-1 accessory protein Vif is controlled uniquely to be low and optimal by proteasome degradation. Microbes Infect/Institut Pasteur 6:791-798. doi: 10.1016/j.micinf.2004.04.011
14. Xiao Z, Ehrlich E, Yu Y, Luo K, Wang T, Tian C, Yu XF (2006) Assembly of HIV-1 Vif-Cul5 E3 ubiquitin ligase through a novel zinc-binding domain-stabilized hydrophobic interface in Vif. Virology 349:290-299. doi: 10.1016/j.virol.2006.02.002
15. Stanley BJ, Ehrlich ES, Short L, Yu Y, Xiao Z, Yu XF, Xiong Y (2008) Structural insight into the human immunodeficiency virus Vif SOCS box and its role in human E3 ubiquitin ligase assembly. J Virol 82:8656-8663. doi: 10.1128/JVI.00767-08
16. Nathans R, Cao H, Sharova N, Ali A, Sharkey M, Stranska R, Stevenson M, Rana TM (2008) Small-molecule inhibition of HIV-1 Vif. Nat Biotech 26:1187-1192. doi: 10.1038/nbt.1496
17. Cen S, Peng ZG, Li XY, Li ZR, Ma J, Wang YM, Fan B, You XF, Wang YP, Liu F, Shao RG, Zhao LX, Yu L, Jiang JD (2010) Small molecular compounds inhibit HIV-1 replication through specifically stabilizing APOBEC3G. J Biol Chem 285:16546-16552. doi: 10.1074/jbc.M109.085308
18. Fan G, Li Z, Shen S, Zeng Y, Yang Y, Xu M, Bruhn T, Bruhn H, Morschhauser J, Bringmann G, Lin W (2010) Baculiferins A-O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera. Bioorg Med Chem 18:5466-5474. doi: 10.1016/j.bmc.2010.06.052
19. Idrees Mohammed MKP, Jiang X, Sharova N, Singh G, Stevenson M, Rana TM (2012) SAR and lead optimization of an HIV-1 VIF-APOBEC3G axis inhibitor. ACS Med Chem Lett 3:465-469. doi: 10.1021/ml300037k
20. Zuo T, Liu D, Lv W, Wang X, Wang J, Lv M, Huang W, Wu J, Zhang H, Jin H, Zhang L, Kong W, Yu X (2012) Small-molecule inhibition of human immunodeficiency virus type 1 replication by targeting the interaction between Vif and ElonginC. J Virol 86:5497-5507. doi: 10.1128/JVI.06957-11
21. Lv W, Liu Z, Jin H, Yu X, Zhang L (2007) Three-dimensional structure of HIV-1 VIF constructed by comparative modeling and the function characterization analyzed by molecular dynamics simulation. Org Biomol Chem 5:617-626. doi: 10.1039/b612050d
22. Vemula V, Vurukonda S, Bairi C (2011) Indolizine derivatives: recent advances and potential pharmacological activities. Int J Pharm Sci Rev Res 11:159-163
23. Singh GS, Mmatli EE (2011) Recent progress in synthesis and bioactivity studies of indolizines. Eur J Med Chem 46:5237-5257. doi: 10.1016/j.ejmech.2011. 08.042
24. Wang BX, Liu WW, He T, Hu HW (2006) Oxidant promoted 1, 3-dipolar cycloaddition of pyridinium ylides to chalcones for preparation of 1-benzoyl-2-arylindolizines. Chin J Chem 24:279-281
25. Gomez O, Salgado-Zamor H, Reyes A, Campos ME (2011) A revised approach to the synthesis of 3-acyl imidazo [1,2-a] pyridines. Heterocycl Comm 16:99-104
26. Stanley BJ, Ehrlich ES, Short L, Yu Y, Xiao Z, Yu XF, Xiong Y (2008) Structural insight into the human immunodeficiency virus Vif SOCS box and its role in human E3 ubiquitin ligase assembly. J Virol 82:8656-8663
27. Marcsisin SR, Engen JR (2010) Molecular insight into the conformational dynamics of the Elongin BC complex and its interaction with HIV-1 Vif. J Mol Biol 402:892-904