(Z)-2-(4-thiazolyl)-2-(trityloxyimino)acetic acid | 73151-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (Z)-2-(4-thiazolyl)-2-(trityloxyimino)acetic acid
• 英文别名: (2Z)-2-(1,3-thiazol-4-yl)-2-trityloxyiminoacetic acid
• CAS: 73151-05-0
• 化学式: C₂₄H₁₈N₂O₃S
• 分子量: 414.485
• InChiKey: RCYILWXNSCVJFK-ROMGYVFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-2-(4-thiazolyl)-2-(trityloxyimino)acetic acid 在 三氯化铝 、 potassium carbonate 、 甲基磺酰氯 作用下， 以 硝基甲烷 、 N,N-二甲基乙酰胺 、 苯甲醚 为溶剂， 反应 1.0h， 生成 7β-[(Z)-2-(thiazol-4-yl)-2-(hydroxyimino)acetamido]-3-[(4-pyrazolyl)methylthio]-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Orally Active Cephalosporins. Part 4: Synthesis, Structure–Activity Relationships and Oral Absorption of Novel 3-(4-Pyrazolylmethylthio)cephalosporins with Various C-7 Side Chains

  摘要：

  A series of 3-(4-pyrazolylmethylthio)cephalosporins with various C-7 side chains was designed, synthesized and evaluated for antibacterial activity and oral absorption in rats. Antibacterial activity against Haemophilus influenzae was markedly increased by the C-7 oxime moiety. Deamination at the 2 position of, or introduction of a substituent such as halogen or methyl to, the 5 position of the (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino) moiety improved oral absorption. Among these compounds, FR192752 (40a) having a (Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-hydroxyiminoacetam do moiety, showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including H. influenzae and penicillin G-resistant Streptococcus pneumoniae (PRSP). Further, it showed higher oral absorption than CFDN and FK041. (C) 2002 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00416-3
• 作为产物：
  描述：

  ethyl (2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetate 在 sodium hydroxide 、 叔丁基硝酸酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 (Z)-2-(4-thiazolyl)-2-(trityloxyimino)acetic acid
  参考文献：
  名称：

  Orally Active Cephalosporins. Part 4: Synthesis, Structure–Activity Relationships and Oral Absorption of Novel 3-(4-Pyrazolylmethylthio)cephalosporins with Various C-7 Side Chains

  摘要：

  A series of 3-(4-pyrazolylmethylthio)cephalosporins with various C-7 side chains was designed, synthesized and evaluated for antibacterial activity and oral absorption in rats. Antibacterial activity against Haemophilus influenzae was markedly increased by the C-7 oxime moiety. Deamination at the 2 position of, or introduction of a substituent such as halogen or methyl to, the 5 position of the (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino) moiety improved oral absorption. Among these compounds, FR192752 (40a) having a (Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-hydroxyiminoacetam do moiety, showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including H. influenzae and penicillin G-resistant Streptococcus pneumoniae (PRSP). Further, it showed higher oral absorption than CFDN and FK041. (C) 2002 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00416-3

文献信息

• Cephem compounds
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0150458A2

  公开（公告）日：1985-08-07

  A cephem compound represent by the general formula wherein, R' represents hydrogen or lower alkyl, R2 and R3 are the same or different and each represents hydrogen or lower alkyl, R4 represents carboxyl or esterified carboxyl, and n represents 0 or 1, a salt of the cephem compound, and a process for producing the cephem compound or a salt thereof. Compounds of the above formula and salts thereof are valuable as antibacterial agents and are especially useful as oral drugs in the prevention or treatment of bacterial infectious diseases.

  一种由通式表示的头孢氨苄化合物 其中，R'代表氢或低级烷基，R2和R3相同或不同且各自代表氢或低级烷基，R4代表羧基或酯化羧基，n代表0或1，一种头孢菌素化合物的盐，以及一种生产头孢菌素化合物或其盐的工艺。上式化合物及其盐作为抗菌剂很有价值，特别是作为口服药物用于预防或治疗细菌感染性疾病。
• US4705784A
  申请人：——

  公开号：US4705784A

  公开（公告）日：1987-11-10
• Orally Active Cephalosporins. Part 4: Synthesis, Structure–Activity Relationships and Oral Absorption of Novel 3-(4-Pyrazolylmethylthio)cephalosporins with Various C-7 Side Chains
  作者：Hirofumi Yamamoto、Yoshiteru Eikyu、Shinya Okuda、Kohji Kawabata、Hisashi Takasugi、Hirokazu Tanaka、Satoru Matsumoto、Yoshimi Matsumoto、Shuichi Tawara

  DOI：10.1016/s0968-0896(01)00416-3

  日期：2002.5

  A series of 3-(4-pyrazolylmethylthio)cephalosporins with various C-7 side chains was designed, synthesized and evaluated for antibacterial activity and oral absorption in rats. Antibacterial activity against Haemophilus influenzae was markedly increased by the C-7 oxime moiety. Deamination at the 2 position of, or introduction of a substituent such as halogen or methyl to, the 5 position of the (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino) moiety improved oral absorption. Among these compounds, FR192752 (40a) having a (Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-hydroxyiminoacetam do moiety, showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including H. influenzae and penicillin G-resistant Streptococcus pneumoniae (PRSP). Further, it showed higher oral absorption than CFDN and FK041. (C) 2002 Elsevier Science Ltd, All rights reserved.