(6R,7R)-3-Chloro-8-oxo-7-[2-(thiazol-2-ylsulfanyl)-acetylamino]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 115339-25-8

• 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: (6R,7R)-3-Chloro-8-oxo-7-[2-(thiazol-2-ylsulfanyl)-acetylamino]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 英文别名: (6R,7R)-3-chloro-8-oxo-7-[[2-(1,3-thiazol-2-ylsulfanyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 115339-25-8
• 化学式: C₁₂H₁₀ClN₃O₄S₃
• 分子量: 391.88
• InChiKey: MECWHJJHXOMQFI-GMSGAONNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  178
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-氨基-3-氯-3-头孢环-4-羧酸 在 sodium hydroxide 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 4.0h， 生成 (6R,7R)-3-Chloro-8-oxo-7-[2-(thiazol-2-ylsulfanyl)-acetylamino]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Oral absorption of cephalosproin antibiotics 2. Expanded structure-activity relationships of 7-arylacetamido-3-substituted cephalosporins

  摘要：

  The structure-activity relationship for 7-arylacetamido cephalosporins has been extended. Modifications of the 7-aryl group led to improvements in microbiological activity against Gram-positive organisms. However, Gram-negative activity was generally much poorer than that of the lead compound 7-[(2-aminothiazol-4-yl)acetamido]-3-chloro-cephalosporanic acid (A). Modifications of the 3-position did not significantly change the microbiological activity or spectrum. Of the compounds selected for mouse protection studies (ED50's), 7-[(benzothien-3-yl)acetamido]-3-chloro cephalosporin and A showed the best per oral to subcutaneous ED50 ratios.

  DOI：

  10.1021/jm00118a023

文献信息

• PFEIL-DOYLE, JANICE;DRAHEIM, SUSAN E.;KUKOLJA, STJEPAN;OTT, JOHN L.;COUNT+, J. MED. CHEM., 31,(1988) N 10, C. 1993-1997
  作者：PFEIL-DOYLE, JANICE、DRAHEIM, SUSAN E.、KUKOLJA, STJEPAN、OTT, JOHN L.、COUNT+

  DOI：——

  日期：——
• Oral absorption of cephalosproin antibiotics 2. Expanded structure-activity relationships of 7-arylacetamido-3-substituted cephalosporins
  作者：Janice Pfeil-Doyle、Susan E. Draheim、Stjepan Kukolja、John L. Ott、Fred T. Counter

  DOI：10.1021/jm00118a023

  日期：1988.10

  The structure-activity relationship for 7-arylacetamido cephalosporins has been extended. Modifications of the 7-aryl group led to improvements in microbiological activity against Gram-positive organisms. However, Gram-negative activity was generally much poorer than that of the lead compound 7-[(2-aminothiazol-4-yl)acetamido]-3-chloro-cephalosporanic acid (A). Modifications of the 3-position did not significantly change the microbiological activity or spectrum. Of the compounds selected for mouse protection studies (ED50's), 7-[(benzothien-3-yl)acetamido]-3-chloro cephalosporin and A showed the best per oral to subcutaneous ED50 ratios.