ethyl 2-methoximino-3-oxo-4-<(3-methoxyphenyl)thio>butyrate | 95835-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 2-methoximino-3-oxo-4-<(3-methoxyphenyl)thio>butyrate
• 英文别名: Ethyl 2-methoxyimino-3-oxo-4-(3-methoxyphenylthio)butyrate；ethyl 2-methoxyimino-4-(3-methoxyphenyl)sulfanyl-3-oxobutanoate
• CAS: 95835-05-5
• 化学式: C₁₄H₁₇NO₅S
• 分子量: 311.359
• InChiKey: HAONOPRLBUUFJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  410.7±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  99.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-methoximino-3-oxo-4-<(3-methoxyphenyl)thio>butyrate 在 sodium hydroxide 、 甲酸 、 草酰氯 、 甲烷磺酸 、 碳酸氢钠 、 N,N-二甲基甲酰胺 、 锌 作用下， 以 甲醇 、 乙醇 、 水 、 丙酮 、 苯 为溶剂， 反应 7.25h， 生成 (R)-7-<(6-methoxy-3-benzothienyl)glycylamido>-3-methyl-3-cephem-4-carboxylic acid
  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：

  sodium 3-methoxy-benzenethiolate 、 4-溴-2-甲氧亚胺乙酰乙酸乙酯 在 水 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 16.17h， 以to afford 16.28 g of ethyl 2-methoxyimino-3-oxo-4-(3-methoxyphenylthio)butyrate的产率得到ethyl 2-methoximino-3-oxo-4-<(3-methoxyphenyl)thio>butyrate
  参考文献：
  名称：

  Benzothienylglycyl cephalosporin derivatives

  摘要：

  7-(3-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，并且具有口服有效性。

  公开号：

  US04492693A1

文献信息

• Benzothienylglycyl cephalosporin derivatives
  申请人：Eli Lilly and Company

  公开号：US04492693A1

  公开（公告）日：1985-01-08

  7-(3-Benzothienyl)glycylamido cephalosporins have good gram positive activity and favorable pharmacokinetics and are orally effective.

  7-(3-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，并且具有口服有效性。
• 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.