(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 | 768399-58-2

• 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: (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
• CAS: 768399-58-2
• 化学式: C₂₁H₂₀FIN₆O₆S₂
• 分子量: 662.461
• InChiKey: WVQGSCKRIBNCMJ-BIRGHMBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：

  (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 在 三氟乙酸 作用下， 以 苯甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成
  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-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-fluoromethoxyiminoacetyl chloride 在 N,O-双三甲硅基乙酰胺 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.5h， 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

文献信息

• A New Method for Regioselective Synthesis of a Broad-Spectrum Parenteral S-3578-Related Cephalosporin Bearing an Imidazo[4,5-b]pyridinium Derivative at C-3’
  作者：Hidenori Yoshizawa、Katsuki Yokoo、Takashi Nomura、Takafumi Ohara、Koji Ishikura、Yasuhiro Nishitani

  DOI：10.3987/com-04-10097

  日期：——

  A broad-spectrum S-3578-related cephalosporin, 7beta-[2-(5-amino- 1,2,4-thiadiazol-3 -yl)-2(Z)-fluoromethoxyiminoacetamido]-3-[1-(3-methylamino-propyl)-1H-imidazo[4,5-b]pyridinium-4-yl]methyl-3-cephem-4-carboxylate sulfate was regioselectively synthesized in a good yield using diaminopyridine derivative bearing a dimethylformarmidine group.