(6R,7R)-7-[(S)-2-(1-Acetyl-2,3-dihydro-1H-indol-5-yl)-2-amino-acetylamino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 98855-90-4

• 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-[(S)-2-(1-Acetyl-2,3-dihydro-1H-indol-5-yl)-2-amino-acetylamino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 98855-90-4
• 化学式: C₂₀H₂₂N₄O₅S
• 分子量: 430.484
• InChiKey: VQQFSAPTJSNLHX-QMTMVMCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  133.04
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (1-Acetyl-2,3-dihydro-1H-indol-5-yl)-allyloxycarbonylamino-acetic acid 在 四(三苯基膦)钯 、 三正丁基氢锡 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 四氢呋喃 、 丙酮 、 乙腈 为溶剂， 反应 5.75h， 生成 (6R,7R)-7-[(S)-2-(1-Acetyl-2,3-dihydro-1H-indol-5-yl)-2-amino-acetylamino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid

  摘要：

  Three positional analogues (4-, 5-, and 7-) of benzothienylglycine and (N-acetylindolinyl)-5-glycine were prepared and coupled to 7-aminodeacetoxycephalosporanic acid (7-ADCA) to give the cephalosporins 17a-c. In addition two isomeric (2,3-b and 3,2-b) thienothiopheneglycines were synthesized and coupled to 7-ADCA to yield cephalosporins 30d and 30e. In vitro testing of these new cephalosporins indicates good activity against Gram-positive bacteria. Against Streptococcus pneumoniae infections compound 25 displayed better mouse protection (both orally and subcutaneously) than cephalexin.

  DOI：

  10.1021/jm00150a023

文献信息

• Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid
  作者：Stjepan Kukolja、Susan E. Draheim、Bernard J. Graves、David C. Hunden、Janice L. Pfeil、Robin D. G. Cooper、John L. Ott、Fred T. Counter

  DOI：10.1021/jm00150a023

  日期：1985.12

  Three positional analogues (4-, 5-, and 7-) of benzothienylglycine and (N-acetylindolinyl)-5-glycine were prepared and coupled to 7-aminodeacetoxycephalosporanic acid (7-ADCA) to give the cephalosporins 17a-c. In addition two isomeric (2,3-b and 3,2-b) thienothiopheneglycines were synthesized and coupled to 7-ADCA to yield cephalosporins 30d and 30e. In vitro testing of these new cephalosporins indicates good activity against Gram-positive bacteria. Against Streptococcus pneumoniae infections compound 25 displayed better mouse protection (both orally and subcutaneously) than cephalexin.