Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl] oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824)

Journal of Medicinal Chemistry

Volumn 55, Issue 1, 2012, Pages 312-326

  Blaser, Adrian ^a   Palmer, Brian D ^a   Sutherland, Hamish S ^a   Kmentova, Iveta ^a   Franzblau, Scott G ^b   Wan, Baojie ^b   Wang, Yuehong ^b   Ma, Zhenkun ^c   Thompson, Andrew M ^a   Denny, William A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^c GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3 BROMOPHENYL) 3 [2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL]UREA; 1 [2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL 3 [4' (TRIFLUOROMETHOXY)BIPHENYL 3 YL]UREA; 1 [2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL] 3 [4 (TRIFLUOROMETHOXY)PHENYL]THIOUREA; 1 [2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL] 3 [4 (TRIFLUOROMETHOXY)PHENYL]UREA; 2 (4 BROMOPHENYL) N [2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL]ACETAMIDE; 2 [[2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL]AMINO] 1 [4 (TRIFLUOROMETHOXY)PHENYL]ETHANONE; 2 NITRO 6 [[2 (TRIFLUOROMETHOXY)BENZYL]OXY] 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZINE; 2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL 4 [4 (TRIFLUOROMETHOXY)PHENYL]ACETAMIDE; 2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL 4 [4 (TRIFLUOROMETHOXY)PHENYL]CARBAMATE; 2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL 4 [4 (TRIFLUOROMETHOXY)PHENYL]PIPERAZINE 1 CARBOXYLATE; 2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL(3 BROMOPHENYL]CARBAMATE; 2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL[4' TRIFLUOROMETHYL)BIPHENYL 3 YL]CARBAMATE; 4 (TRIFLUOROMETHOXY)PHENYL[2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL]CARBAMATE; 4 IODOBENZYL[2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL]CARBAMATE; 6,7 DIHYDRO 2 NITRO 6 (4 TRIFLUOROMETHOXYBENZYLOXY) 5H IMIDAZO[2,1 B][1,3]OXAZINE; [4' (TRIFLUOROMETHYL)BIPHENYL 4 YL]METHYL[2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL]CARBAMATE; AMIDE; CARBAMIC ACID DERIVATIVE; DELAMANID; N [2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL] 2 (TRIFLUOROMETHOXY)BENZAMIDE; N [2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL] 2 (TRIFLUOROMETHOXY)BENZENESULFONAMIDE; N [2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL] 2 [4 (TRIFLUOROMETHYL)BIPHENYL 4 YL]ACETAMIDE; N METHYL N[2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL] 2 (TRIFLUOROMETHOXY)BENZAMIDE; N METHYL N[2 NITRO 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZIN 6 YL] 2 (TRIFLUOROMETHOXY)BENZENESULFONAMIDE; UNCLASSIFIED DRUG; UREA;

AEROBIC METABOLISM; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG POTENCY; IN VIVO STUDY; LIPOPHILICITY; MALE; MOUSE; MYCOBACTERIUM BOVIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; RAT; SINGLE DRUG DOSE; SOLUBILITY; STRUCTURE ACTIVITY RELATION; TUBERCULOSIS;

ACUTE DISEASE; AMIDES; ANIMALS; ANTITUBERCULAR AGENTS; BICYCLO COMPOUNDS, HETEROCYCLIC; BIOLOGICAL AVAILABILITY; BIPHENYL COMPOUNDS; CARBAMATES; CHRONIC DISEASE; DOGS; HUMANS; MICE; MICROBIAL SENSITIVITY TESTS; MICROSOMES, LIVER; MODELS, MOLECULAR; MYCOBACTERIUM TUBERCULOSIS; NITROIMIDAZOLES; PIPERAZINES; RATS; SOLUBILITY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TUBERCULOSIS, PULMONARY; UREA;

EID: 84862960230     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2012276     Document Type: Article

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