ethyl α-(hydroxyimino)-α-(4,5,6,7-tetrahydro-2-benzothienyl)acetate | 95361-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: ethyl α-(hydroxyimino)-α-(4,5,6,7-tetrahydro-2-benzothienyl)acetate
• 英文别名: Ethyl alpha-hydroxyimino-alpha-(4,5,6,7-tetrahydro-2-benzothienyl)acetate；ethyl 2-hydroxyimino-2-(4,5,6,7-tetrahydro-1-benzothiophen-2-yl)acetate
• CAS: 95361-95-8
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: GWWSSMWLMLEALS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 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：
  87.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl α-(hydroxyimino)-α-(4,5,6,7-tetrahydro-2-benzothienyl)acetate 在 sodium hydroxide 、 甲酸 、 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 38.5h， 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：

  4,5,6,7-四氢-1-苯并噻吩 在 三氯化铝 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 ethyl α-(hydroxyimino)-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。
• 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.