Design, synthesis, protein-ligand X-ray structure, and biological evaluation of a series of novel macrocyclic human immunodeficiency virus-1 protease inhibitors to combat drug resistance

Journal of Medicinal Chemistry

Volumn 52, Issue 23, 2009, Pages 7689-7705

  Ghosh, Arun K ^a   Kulkarni, Sarang ^a   Anderson, David D ^a   Hong, Lin ^b   Baldridge, Abigail ^a   Wang, Yuan Fang ^d   Chumanevich, Alexander A ^d   Kovalevsky, Andrey Y ^d   Tojo, Yasushi ^e   Amano, Masayuki ^e   Koh, Yasuhiro ^e   Tang, Jordan ^b,c   Weber, Irene T ^d   Mitsuya, Hiroaki ^e,f  

^a PURDUE UNIVERSITY   (United States)

^b OKLAHOMA MEDICAL RESEARCH FOUNDATION   (United States)

^c UNIVERSITY OF OKLAHOMA COLLEGE OF MEDICINE   (United States)

^d GEORGIA STATE UNIVERSITY   (United States)

^e KUMAMOTO UNIV SCHOOL OF MEDICINE   (Japan)

^f NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (ALLYLOXY) 3 METHOXYBENZEN; 1 (BUT 3 ENYLOXY) 3 METHOXYBENZENE; 1 (HEX 5 ENYLOXY) 3 METHOXYBENZENE; 1 METHOXY 3 (PENT 4 ENYLOXY)BENZENE; 2 (ALLYLOXY) 4 METHOXYBENZENESULFONIC ACID; 2 (ALLYLOXY) 4METHOXYBENZENE 1 SULFONYL CHLORIDE; 2 (BUT 3 ENYLOXY) 4 METHOXYBENZENE 1 SULFONYL CHLORIDE; 2 (BUT 3 ENYLOXY) 4 METHOXYBENZENESULFONIC ACID; 2 (HEX 5 ENYLOXY) 4 METHOXYBENZENE 1 SULFONYL CHLORIDE; 4 METHOXY 2 (PENT 4 ENYLOXY)BENZENE 1 SULFONYL CHLORIDE; 4 METHOXY 2 (PENT 4 ENYLOXY)BENZENESULFONIC ACID; AMPRENAVIR; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; DARUNAVIR; INDINAVIR; LIGAND; LOPINAVIR; METHYL GROUP; PROTEINASE INHIBITOR; SAQUINAVIR; TERT BUTYL 4 (ALLYLAMINO) 3 HYDROXY 1 PHENYLBUTAN 2 YLCARBAMATE; TERT BUTYL 4 (HEX 5 ENYLAMINO) 3 HYDROXY 1 PHENYLBUTAN 2 YLCARBAMATE; TERT BUTYL 4 [2 (ALLYLOXY) N (HEX 5 ENYL) 4 METHOXYPHENYLSULFONAMIDO] 3 HYDROXY 1 PHENYLBUTAN 2 YLCARBAMATE; TERT BUTYL 4 [2 (BUT 3 ENYLOXY) N (HEX 5 ENYL) 4 METHOXYPHENYLSULFONAMIDO] 3 HYDROXY 1 PHENYLBUTAN 2 YLCARBAMATE; TERT BUTYL 4 [N (HEX 5 ENYL) 2 (HEX 5 ENYLOXY) 4 ETHOXYPHENYLSULFONAMIDO] 3 HYDROXY 1 PHENYLBUTAN 2 YLCARBAMATE; TERT BUTYL 4 [N (HEX 5 ENYL) 4 METHOXY 2 (PENT 4 ENYLOXY)PHENYLSULFONAMIDO] 3 HYDROXY 1 PHENYLBUTAN 2 YLCARBAMATE; TERT BUTYL 4 [N ALLYL 2 (ALLYLOXY) 4 METHOXYPHENYLSULFONAMIDO] 3 HYDROXY 1 PHENYLBUTAN 2 YLCARBAMATE; TERT BUTYL 4 [N ALLYL 2 (BUT 3 ENYLOXY) 4 METHOXYPHENYLSULFONAMIDO] 3 HYDROXY 1 PHENYLBUTAN 2 YLCARBAMATE; TERT BUTYL 4 [N ALLYL 2 (HEX 5 ENYLOXY) 4 METHOXYPHENYLSULFONAMIDO] 3 HYDROXY 1 PHENYLBUTAN 2 YLCARBAMATE; TERT BUTYL4 [N ALLYL 4 METHOXY 2 (PENT 4 ENYLOXY)PHENYLSULFONAMIDO] 3 HYDROXY 1 PHENYLBUTAN 2 YLCARBAMATE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BINDING SITE; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROGEN BOND; HYDROPHOBICITY; LIGAND BINDING; MULTIDRUG RESISTANCE; NONHUMAN; PROTEINASE INHIBITION; VIRUS RESISTANCE; VIRUS STRAIN; VIRUS VIABILITY; X RAY CRYSTALLOGRAPHY;

ANTI-HIV AGENTS; CELL LINE; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; DRUG RESISTANCE, VIRAL; HIV PROTEASE; HIV PROTEASE INHIBITORS; HIV-1; HUMANS; LIGANDS; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MUTATION;

EID: 72249085558     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900695w     Document Type: Article

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