2-(1-Benzothiophen-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid | 95361-77-6

• 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: 2-(1-Benzothiophen-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
• CAS: 95361-77-6
• 化学式: C₁₅H₁₇NO₄S
• 分子量: 307.37
• InChiKey: CUDUHPYLXIEURW-UHFFFAOYSA-N

物化性质

• 沸点：
  497.7±40.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1-Benzothiophen-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid 在 碳酸氢钠 、 对甲苯磺酸 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.0h， 生成 (6R,7R)-7-(2-Amino-2-benzo[b]thiophen-4-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 benzo[b]thiophen-4-yl acetate 在 sodium hydroxide 、 甲酸 、 亚硝酸丁酯 、 sodium ethanolate 、 三乙胺 、 锌 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 2-(1-Benzothiophen-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic 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

• Improvements in or relating to benzothienyl cephalosporin antibiotics
  申请人：ELI LILLY AND COMPANY

  公开号：EP0122158A2

  公开（公告）日：1984-10-17

  Novel 4, 5, 6, or 7-dihydro- and benzothienyl cephalosporins are useful in the oral treatment of gram positive bacterial infections.

  新型 4、5、6 或 7-二氢和苯并噻吩头孢菌素可用于口服治疗革兰氏阳性细菌感染。
• GRAVES, B. J.;KUKOLJA, S.
  作者：GRAVES, B. J.、KUKOLJA, S.

  DOI：——

  日期：——
• US4501741A
  申请人：——

  公开号：US4501741A

  公开（公告）日：1985-02-26
• 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.