(6R,7R)-7-(2-Bromo-acetylamino)-3-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 85690-93-3

• 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)-7-(2-Bromo-acetylamino)-3-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 英文别名: (6R,7R)-7-[(2-bromoacetyl)amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 85690-93-3
• 化学式: C₉H₈BrClN₂O₄S
• 分子量: 355.597
• InChiKey: QUGZBLKTFOOBSN-SVGQVSJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-巯基噻唑 、 (6R,7R)-7-(2-Bromo-acetylamino)-3-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 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
• 作为产物：
  描述：

  7-氨基-3-氯-3-头孢环-4-羧酸 生成 (6R,7R)-7-(2-Bromo-acetylamino)-3-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Cephalosporin compound
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0068403B1

  公开（公告）日：1986-08-13
• US4477659A
  申请人：——

  公开号：US4477659A

  公开（公告）日：1984-10-16
• 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.
• 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：——