diphenylmethyl 7β-[(Z)-2-(2-amino-5-methylthiazol-4-yl)-2-(hydroxyimino)acetamido]-3-[(4-pyrazolyl)methylthio]-3-cephem-4-carboxylate | 189099-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: diphenylmethyl 7β-[(Z)-2-(2-amino-5-methylthiazol-4-yl)-2-(hydroxyimino)acetamido]-3-[(4-pyrazolyl)methylthio]-3-cephem-4-carboxylate
• 英文别名: benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-5-methyl-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-(1H-pyrazol-4-ylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 189099-43-2
• 化学式: C₃₀H₂₇N₇O₅S₃
• 分子量: 661.786
• InChiKey: QYRJRMSOYJWCGH-DZBKVFFFSA-N

物化性质

• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  255
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  diphenylmethyl 7β-[(Z)-2-(2-amino-5-methylthiazol-4-yl)-2-(hydroxyimino)acetamido]-3-[(4-pyrazolyl)methylthio]-3-cephem-4-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 、 苯甲醚 为溶剂， 以31%的产率得到7β-[(Z)-2-(2-amino-5-methylthiazol-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-(Z)-hydroxyimino-3-oxopentanoate 在 sodium hydroxide 、 磺酰氯 、 sodium hydride 、 三乙胺 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.5h， 生成 diphenylmethyl 7β-[(Z)-2-(2-amino-5-methylthiazol-4-yl)-2-(hydroxyimino)acetamido]-3-[(4-pyrazolyl)methylthio]-3-cephem-4-carboxylate
  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

• US6159961A
  申请人：——

  公开号：US6159961A

  公开（公告）日：2000-12-12