(6R,7R)-7-((R)-2-Benzo[b]thiophen-5-yl-2-tert-butoxycarbonylamino-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester | 95361-87-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6R,7R)-7-((R)-2-Benzo[b]thiophen-5-yl-2-tert-butoxycarbonylamino-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS: 95361-87-8
• 化学式: C₃₀H₃₀N₄O₈S₂
• 分子量: 638.722
• InChiKey: NWLUKCQNQACUGV-AZSVPQILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  157.18
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (6R,7R)-7-((R)-2-Benzo[b]thiophen-5-yl-2-tert-butoxycarbonylamino-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester 在 碳酸氢钠 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以73%的产率得到(6R,7R)-7-((R)-2-Amino-2-benzo[b]thiophen-5-yl-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester
  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
• 作为产物：
  描述：

  ethyl 2-oxo-2-(4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-5-yl)acetate 在 sodium hydroxide 、 sodium tetrahydroborate 、 甲酸 、 亚硝酸丁酯 、 sodium ethanolate 、 对甲苯磺酸 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 10.5h， 生成 (6R,7R)-7-((R)-2-Benzo[b]thiophen-5-yl-2-tert-butoxycarbonylamino-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester
  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