Synthesis and SAR study of novel 7-(pyridinium-3-yl)-carbonyl imidazo[5,1-b]thiazol-2-yl carbapenems

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 1, 2007, Pages 392-402

  Maruyama, Takahisa ^a   Kano, Yuko ^a   Yamamoto, Yasuo ^a   Kurazono, Mizuyo ^a   Iwamatsu, Katsuyoshi ^a   Atsumi, Kunio ^a   Shitara, Eiki ^a  

^a MEIJI SEIKA KAISHA LTD   (Japan)

Author keywords

7 Heterocyclic carbonyl imidazo 5,1 b thiazol 2 yl group; Anti MRSA activity; BLNAR; Carbapenem; Imidazo 5,1 b thiazole; MRSA; PRSP

Indexed keywords

2 [7 (1 ACETOXYMETHYLPYRIDINIUM 3 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 5 (1 HYDROXYETHYL) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 2 [7 (1 BENZYLPYRIDINIUM 3 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 5 (1 HYDROXYETHYL) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 2 [7 (1 CARBAMOYLMETHYLPYRIDINIUM 3 YL)CARBONYL 5 (MORPHILIN 1 YL)IMIDAZO[5,1 B]THIAZOL 2 YL] 6 (1 HYDROXYETHY) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 2 [7 (1 CARBAMOYLMETHYLPYRIDINIUM 3 YL)CARBONYL 5 CHLOROIMIDAZO[5,1 B]THIAZOL 2 YL] 6 (1 HYDROXYETHY) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 2 [7 (1 CARBAMOYLMETHYLPYRIDINIUM 3 YL)CARBONYL 5 CYCLOPROPYLIMIDAZO[5,1 B]THIAZOL 2 YL] 6 (1 HYDROXYETHY) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 2 [7 (1 CARBAMOYLMETHYLPYRIDINIUM 3 YL)CARBONYL 5 ETHYLIMIDAZO[5,1 B]THIAZOL 2 YL] 6 (1 HYDROXYETHY) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 2 [7 (1 CARBAMOYLMETHYLPYRIDINIUM 3 YL)CARBONYL 5 METHYLIMIDAZO[5,1 B]THIAZOL 2 YL] 6 (1 HYDROXYETHY) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 2 [7 (1 CARBAMOYLMETHYLPYRIDINIUM 3 YL)CARBONYL 5 METHYLTHIOIMIDAZO[5,1 B]THIAZOL 2 YL] 6 (1 HYDROXYETHY) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 2 [7 (1 CARBAMOYLMETHYLPYRIDINIUM 3 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 5 (1 HYDROXYETHYL) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 2 [7 (1 CARBOXYMETHYLPYRIDINIUM 3 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 5 (1 HYDROXYETHYL) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 2 [7 (1 ETHOXYCARBONYLMETHYLPYRIDINIUM 3 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 5 (1 HYDROXYETHYL) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 2 [7 [1 [2(N,N DIMETHYLAMINO)ETHYL]PYRIDINIUM 3 YL]CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 6 (1 HYDROXYETHYL) 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLATE; 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (1 METHYLPYRIDINIUM 3 Y)CARBONYLIMIDAZO[5, 1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLIC ACID; 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (1 METHYLPYRIDINIUM 3 YL) CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLATE; 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (1 TRIFLUOROACETOXYMETHYLPYRIDINIUM 3 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLATE; 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (PIPERIDIN 2 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLIC ACID; 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (PIPERIDIN 4 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLIC ACID; 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (PYRIDIN 3 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLIC ACID; 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (PYRROLIDIN 2 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLIC ACID; 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 [1 (2 SULFAMOYLAMINOETHYL)PYRIDINIUM 3 Y)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLIC ACID; 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 [1 [2(METHANESULFONYL)ETHYL]PYRIDINIUM 3 YL]CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLATE; 6 (1 HYDROXYETHYL) 2 [7 (4 HYDROXYPYRROLIDIN 2 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 METHYL 1 CARBAPEN 2 EM 3 CARBOXYLIC ACID; CARBAPENEM DERIVATIVE; SODIUM 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (1 METHYLINDOL 3 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 3 YL] 1 CARBAPEN 2 EM 3 CARBOXYLATE; SODIUM 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (PYRIDIN 4 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLATE; SODIUM 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (QUINOLIN 3 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLATE; SODIUM 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (THIAZOL 5 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLATE; SODIUM 6 (1 HYDROXYETHYL) 1 METHYL 2 [7 (THIOPHEN 2 YL)CARBONYLIMIDAZO[5,1 B]THIAZOL 2 YL] 1 CARBAPEN 2 EM 3 CARBOXYLATE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; GRAM POSITIVE BACTERIUM; HAEMOPHILUS INFLUENZAE; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; PENICILLIN RESISTANCE; STREPTOCOCCUS PNEUMONIAE; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; CARBAPENEMS; HAEMOPHILUS INFLUENZAE; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; PYRIDINIUM COMPOUNDS; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM; STREPTOCOCCUS PNEUMONIAE; STRUCTURE-ACTIVITY RELATIONSHIP;

HAEMOPHILUS INFLUENZAE; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; POSIBACTERIA; STREPTOCOCCUS PNEUMONIAE;

EID: 33750946976     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.09.049     Document Type: Article

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