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J-GLOBAL ID：200902111694274933   Reference number：94A0411652

Synthesis and structure-activity relationships of 7β-[(Z)-2-(2-aminothiazol-4-yl)-3-(substituted)-2-propenoylamino]-3-cephems with C-3 substitutions.

C3位に置換基を有する7β-[(Z)-2-(2-アミノチアゾール-4-イル)-3-(置換)-2-プロペノイルアミノ]-3-セフェム類の合成と構造活性相関

Author (9)： ISHIKURA K (Shionogi & Co., Ltd., Osaka, JPN) ,  KUBOTA T (Shionogi & Co., Ltd., Osaka, JPN) ,  MINAMI K (Shionogi & Co., Ltd., Osaka, JPN) ,  HAMASHIMA Y (Shionogi & Co., Ltd., Osaka, JPN) ,  NAKASHIMIZU H (Shionogi & Co., Ltd., Osaka, JPN) ,  MOTOKAWA K (Shionogi & Co., Ltd., Osaka, JPN) ,  KIMURA Y (Shionogi & Co., Ltd., Osaka, JPN) ,  MIWA H (Shionogi & Co., Ltd., Osaka, JPN) ,  YOSHIDA T (Shionogi & Co., Ltd., Osaka, JPN)
Material： Journal of Antibiotics  (J Antibiot)
Volume： 47  Issue： 4  Page： 466-476  Publication year： Apr. 1994 
JST Material Number： G0489A  ISSN： 0021-8820  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： Cephalosporins ,...
Semi thesaurus term： MIC(concentration)

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JST classification (1)： Basic research of antibiotics acting on pathogenic organisms  (GX05020C)

Substance index (20)： (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-butenyl]amino]-3-[(carbamoyloxy)methyl]cepham-3-ene-4-carboxylic acid pivaloyloxymethyl ester ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-butenyl]amino]-3-[(acetyloxy)methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-butenyl]amino]-3-[(carbamoyloxy)methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-butenyl]amino]-3-[[(1,2,3-thiadiazol-5-yl)thio]methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-3-[(acetyloxy)methyl]cepham-3-ene-4-carboxylic acid ,  S-1006 ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-3-chlorocepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-3-ethenylcepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-3-[(Z)-1-propenyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-3-(methoxymethyl)cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-3-[[(1H-1,2,3-triazol-5-yl)thio]methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-2-pentenyl]amino]-3-[(5-methyl-2H-tetrazol-2-yl)methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-4-cyclopentyl-2-butenyl]amino]-3-[(acetyloxy)methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-4-cyclopentyl-2-butenyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-4-(methylthio)-2-butenyl]amino]-3-[(carbamoyloxy)methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-4-(methylthio)-2-butenyl]amino]-3-[[(1,2,3-thiadiazol-5-yl)thio]methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-4-phenyl-2-butenyl]amino]-3-[(carbamoyloxy)methyl]cepham-3-ene-4-carboxylic acid ,  (7R)-7-[[(Z)-2-(2-Amino-4-thiazolyl)-1-oxo-4-phenyl-2-butenyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]cepham-3-ene-4-carboxylic acid

Reference (7)：

• 1) ISHIKURA, K.; T. KUBOTA, K. MINAMI, Y. HAMASHIMA, H. NAKASHIMIZU, K. MOTOKAWA & T. YOSHIDA: Synthesis and structure-activity relationships of 7β-[(Z)-2-(2-aminothiazol-4-yl)-3-(substituted)-2-propenoylamino]-3-desacetoxymethylcephalosporins. J. Antibiotics 47: 453-465, 1994
• 2) HAMASHIMA, Y.; K. ISHIKURA, K. MINAMI, T. KUBOTA & T. YOSHIDA (Shionogi): Alkeneamidecephalosporinester. Jpn. Kokai 89 ('87), Jan. 6, 1987
• 3) KIMURA, Y.; M. NAKANO, H. NAKASHIMIZU, S. NAKAMOTO, Y. WATANABE, S. OTUBO, T. MATSUBARA, S. SATO, H. HARA & T. YOSHIDA: Pharmacokinetics of S-l 108, a new oral cephalosporin, in experimental anaimals. Chemotherapy (Tokyo) 41 (Suppl. 1): 163-176, 1993
• 4) NOMURA, K.; M. Doi & T. YOSHIDA: S-l 108, a new oral cephem antibiotic: stability against β-lactamases and affinity for penicillin-binding proteins. Chemotherapy (Tokyo) 41 (Suppl. 1): 102-108, 1993
• 5) KOBAYASHI, F.; M. OGAWA & T. YOSHIZAKI: Nephrotoxicity study of S-l 108, a new ester-type oral cephem antibiotic, given orally in rabbits. IYAKUHIN KENKYU (Tokyo) 24: 231-243, 1993

Terms in the title (6)： C3 ,  置換基 ,  2-アミノチアゾール ,  置換 ,  セフェム類 ,  構造活性相関