ethyl α-oxo-α-(4,5,6,7-tetrahydro-2-benzothienyl)acetate | 95361-94-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl α-oxo-α-(4,5,6,7-tetrahydro-2-benzothienyl)acetate
• 英文别名: Ethyl alpha-oxo-alpha-(4,5,6,7-tetrahydro-2-benzothienyl)acetate；ethyl 2-oxo-2-(4,5,6,7-tetrahydro-1-benzothiophen-2-yl)acetate
• CAS: 95361-94-7
• 化学式: C₁₂H₁₄O₃S
• 分子量: 238.307
• InChiKey: UIMMWRBTRUNPNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl α-oxo-α-(4,5,6,7-tetrahydro-2-benzothienyl)acetate 在 sodium hydroxide 、 甲酸 、 盐酸羟胺 、 sodium acetate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 41.5h， 生成 p-nitrobenzyl 7--3-methyl-3-cephem-4-carboxylate
  参考文献：
  名称：

  Orally absorbable cephalosporin antibiotics. 1. Structure-activity relationships of benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid

  摘要：

  A structure-activity relationship study of a number of orally absorbed cephalosporins together with their syntheses is described. These new cephalosporins are benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid. Several different synthetic methods for the glycine side chains, their protection, and the final acylations are reported. Several of these analogues were more active than cephalexin both in vitro and in vivo against commonly encountered Gram-positive bacteria. (R)-7-(3-Benzothienylglycylamido)-3-methyl-3-cephem-4-carboxylic acid (1R) has emerged as a potent antibacterial agent and is currently undergoing preclinical evaluation.

  DOI：

  10.1021/jm00150a022
• 作为产物：
  描述：

  4-(2-噻吩基)丁酸 在 sodium hydroxide 、 三氯化铝 、 氯化亚砜 、 四氯化锡 、 肼 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 ethyl α-oxo-α-(4,5,6,7-tetrahydro-2-benzothienyl)acetate
  参考文献：
  名称：

  Orally absorbable cephalosporin antibiotics. 1. Structure-activity relationships of benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid

  摘要：

  A structure-activity relationship study of a number of orally absorbed cephalosporins together with their syntheses is described. These new cephalosporins are benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid. Several different synthetic methods for the glycine side chains, their protection, and the final acylations are reported. Several of these analogues were more active than cephalexin both in vitro and in vivo against commonly encountered Gram-positive bacteria. (R)-7-(3-Benzothienylglycylamido)-3-methyl-3-cephem-4-carboxylic acid (1R) has emerged as a potent antibacterial agent and is currently undergoing preclinical evaluation.

  DOI：

  10.1021/jm00150a022

文献信息

• Benzothienylglycyl cephalosporin derivatives
  申请人：Eli Lilly and Company

  公开号：US04482553A1

  公开（公告）日：1984-11-13

  7-(2-Benzothienyl)glycylamido cephalosporins have good gram positive activity and favorable pharmacokinetics and are orally effective.

  7-(2-苯并噻吩基)甘氨酰头孢菌素具有良好的革兰氏阳性活性和良好的药代动力学特性，并且口服有效。
• Improvements in or relating to benzothienylglycyl cephalosporin derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0122156A2

  公开（公告）日：1984-10-17

  7-(2-Benzothienyl)glycylamido cephalosporins provided by this invention possess favorable pharmacokinetics and are orally-effective against gram positive bacteria.

  本发明提供的 7-(2-苯并噻吩基)甘氨酰头孢菌素具有良好的药代动力学，对革兰氏阳性菌具有口服疗效。
• US4482553A
  申请人：——

  公开号：US4482553A

  公开（公告）日：1984-11-13
• Orally absorbable cephalosporin antibiotics. 1. Structure-activity relationships of benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid
  作者：Stjepan Kukolja、Susan E. Draheim、Janice L. Pfeil、Robin D. G. Cooper、Bernard J. Graves、Richard E. Holmes、David A. Neel、George W. Huffman、J. Alan Webber

  DOI：10.1021/jm00150a022

  日期：1985.12

  A structure-activity relationship study of a number of orally absorbed cephalosporins together with their syntheses is described. These new cephalosporins are benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid. Several different synthetic methods for the glycine side chains, their protection, and the final acylations are reported. Several of these analogues were more active than cephalexin both in vitro and in vivo against commonly encountered Gram-positive bacteria. (R)-7-(3-Benzothienylglycylamido)-3-methyl-3-cephem-4-carboxylic acid (1R) has emerged as a potent antibacterial agent and is currently undergoing preclinical evaluation.