Synthesis and Structure-Activity Relationships for Extended Side Chain Analogues of the Antitubercular Drug (6 S)-2-Nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5 H -imidazo[2,1- b ][1,3]oxazine (PA-824)

Journal of Medicinal Chemistry

Volumn 58, Issue 7, 2015, Pages 3036-3059

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

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

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

^d Faculty of Natural Sciences   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

1 (BROMOMETHYL) 4 [4 (TRIFLUOROMETHOXY)BENZYL]BENZENE; 1 (BROMOMETHYL) 4 [4 (TRIFLUOROMETHOXY)PHENOXY]BENZENE; 1 IODO 4 [4 (TRIFLUOROMETHOXY)PHENOXY]BENZENE; 1 NITRO 4 [4 TRIFLUOROMETHOXY)PHENOXY]BENZENE; 1 [2 [4 (BROMOMETHYL)PHENYL]ETHENYL] 4 (TRIFLUOROMETHOXY)BENZENE; 2 (BROMOMETHYL) 5 [4 (TRIFLUOROMETHOXY)PHENOXY]PYRIDINE; 2 NITRO 6 [[4 (TRIFLUOROMETHOXY)BENZYL]OXY] 6,7 DIHYDRO 5H IMIDAZO[2,1 ][1,3]OXAZINE; 2 NITRO 6 [[4 (TRIFLUOROMETHOXY)PHENOXY][1,1' BIPHENYL] 4 YL]METHOXY] 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZINE; 2 NITRO 6 [[4 [2 [4 (TRIFLUOROMETHOXY)PHENYL]ETHENYL]BENZYL]OXY] 6,7 DIHYDRO 5H IMIDAZO [2,1 B][1,3]OXAZINE; 2 NITRO 6 [[4 [4 (TRIFLUOROMETHOXY)PHENOXY]BENZYL]OXY] 6,7 DIHYDRO 5H IMIDAZO [2,1 B][1,3]OXAZINE; 2 NITRO 6 [[4 [[4 (TRIFLUOROMETHOXY)PHENYL]ETHYNYL]BENZYL]OXY] 6,7 DIHYDRO 5H IMIDAZO[2,1 B][1,3]OXAZINE; 2 NITRO 6 [[4 [[5 (TRIFLUOROMETHYL)PYRIDIN 2 YL]OXY]BENZYL]OXY] 6,7 DIHYDRO 5H IMIDAZO [2,1][1,3]OXAZINE; 2 NITRO 6 [[5 [4 (TRIFLUOROMETHOXY)PHENOXY]PYRIDIN 2 YL]METHOXY] 6,7 DIHYDRO 5H IMIDAZO [2,1 B][1,3]OXAZINE; 2 [4 (BROMOMETHYL)PHENOXY] 5 (TRIFLUOROMETHYL)PYRIDINE; 4 [4 (TRIFLUOROMETHOXY)PHENOXY]ANILINE; 4 [4 (TRIFLUOROMETHOXY)PHENOXY]BENZALDEHYDE; 4 [[5 (TRIFLUOROMETHYL)PYRIDIN 2YL]OXY]BENZALDEHYDE; 5 (4 IODOPHENOXY) 2 (TRIFLUOROMETHYL)PYRIDINE; 5 BROMO 2 [4 (TRIFLUOROMETHOXY)PHENOXY]PYRIDINE; 6 [(4 ETHYNYLBENZYL)OXY] 2 NITRO 6,7 DIHYDRO 5H IMIDAZO [2,1 B][1,3]OXAZINE; METHYL 4 [2 [4 (TRIFLUOROMETHOXY)PHENYL]ETHENYL]BENZOATE; METHYL 4 [4 (TRIFLUOROMETHOXY)BENZYL]BENZOATE; PYRIDINE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG; [4 [2 [4 (TRIFLUOROMETHOXY)PHENYL]ETHENYL]PHEYNYL]METHANOL; [4 [4 (TRIFLUOROMETHOXY)BENZYL]PHENYL]METHANOL; [4 [4 (TRIFLUOROMETHOXY)PHENOXY]PHENYL]METHANOL; [4 [[5 (TRIFLUOROMETHYL)PYRIDIN 2 YL]OXY]PHENYL)METHANOL; [5 [4 (TRIFLUOROMETHOXY)PHENOXY]PYRIDIN 2 YL]METHANOL; 2-NITRO-6-(4-(TRIFLUOROMETHOXY)BENZYLOXY)-6,7-DIHYDRO-5H-IMIDAZO(2,1-B)(1,3)OXAZINE; NITROIMIDAZOLE DERIVATIVE; OPC-67683; OXAZOLE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CLINICAL ASSESSMENT; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG POTENCY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOLERABILITY; HUMAN; HYDROPHILICITY; IN VITRO STUDY; IN VIVO STUDY; LIGAND BINDING; LIPOPHILICITY; MALE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; RAT; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TUBERCULOSIS; ANIMAL; BAGG ALBINO MOUSE; BIOAVAILABILITY; CHEMISTRY; CHRONIC DISEASE; DISEASE MODEL; DRUG EFFECTS; INBRED MOUSE STRAIN; LIVER MICROSOME; METABOLISM; MICROBIAL SENSITIVITY TEST; MICROBIOLOGY; ORAL DRUG ADMINISTRATION; SPRAGUE DAWLEY RAT; SYNTHESIS;

ADMINISTRATION, ORAL; ANIMALS; ANTITUBERCULAR AGENTS; BIOLOGICAL AVAILABILITY; CHEMISTRY TECHNIQUES, SYNTHETIC; CHRONIC DISEASE; DISEASE MODELS, ANIMAL; HUMANS; MALE; MICE, INBRED BALB C; MICE, INBRED STRAINS; MICROBIAL SENSITIVITY TESTS; MICROSOMES, LIVER; MYCOBACTERIUM TUBERCULOSIS; NITROIMIDAZOLES; OXAZOLES; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; TUBERCULOSIS;

EID: 84927584529     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501608q     Document Type: Article

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