p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate | 189507-47-9

• 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: p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate
• 英文别名: (4-methoxyphenyl)methyl (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetyl]amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 189507-47-9
• 化学式: C₂₁H₂₀ClFN₆O₆S₂
• 分子量: 571.01
• InChiKey: JRLAVVQOTVPNRX-BIRGHMBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  212
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 1.5h， 生成 (4-methoxyphenyl)methyl (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetyl]amino]-3-(iodomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  CP6679, a new injectable cephalosporin. Part1: Synthesis and structure–activity relationships

  摘要：

  A series of cephalosporins bearing a 5,5-fused ring system, an (imidazo/[5,1 -b]thiazolium-6-yl)methyl group, at the C-3 position were synthesized and evaluated for in vitro antibacterial activities. CP6679 (Is) and its analogues showed potent antibacterial activities against Gram-positive and Gram-negative bacteria, including Pseudomonas aeruginosa. They were also highly active against methicillin-resistant Staphylococcus aureus (MRSA). CP6679 (Is) showed more potent antibacterial activity than ceftazidime (CAZ) or cefpirome (CPR) against Pseudomonas aeruginosa and MRSA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00214-5
• 作为产物：
  描述：

  2-fluoromethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl)-acetic acid 在 N,O-双三甲硅基乙酰胺 、 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate
  参考文献：
  名称：

  CP6679, a new injectable cephalosporin. Part1: Synthesis and structure–activity relationships

  摘要：

  A series of cephalosporins bearing a 5,5-fused ring system, an (imidazo/[5,1 -b]thiazolium-6-yl)methyl group, at the C-3 position were synthesized and evaluated for in vitro antibacterial activities. CP6679 (Is) and its analogues showed potent antibacterial activities against Gram-positive and Gram-negative bacteria, including Pseudomonas aeruginosa. They were also highly active against methicillin-resistant Staphylococcus aureus (MRSA). CP6679 (Is) showed more potent antibacterial activity than ceftazidime (CAZ) or cefpirome (CPR) against Pseudomonas aeruginosa and MRSA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00214-5

文献信息

• Cephem derivatives
  申请人：Meiji Seika Kabushiki Kaisha

  公开号：US05663162A1

  公开（公告）日：1997-09-02

  Compounds represented by the following formula (I), that is, cephem derivatives having substituted or unsubstituted imidazo[5,1-b]thiazolium-6-yl as a substituent at the 3-position of the cephem ring: ##STR1## wherein X represents CH or N, R.sup.1 represents H, alkyl, alkenyl or the like, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 represent H, alkyl, carbamoyl, amino or the like. The above compounds have excellent antibacterial activity, and useful as medicines for the treatment of various infectious diseases caused by bacteria.

  具有下述通式（I）表示的化合物，即头孢烯环的3位上具有取代或未取代的咪唑并[5,1-b]噻唑鎓-6-基作为取代基的头孢烯衍生物：##STR1## 其中X代表CH或N，R1代表H、烷基、烯基等，R2、R3、R4和R5代表H、烷基、氨甲酰基、氨基等。上述化合物具有优异的抗菌活性，可作为治疗由细菌引起的各种感染性疾病的药物。