[(Z)-Hydroxyimino]-(6-methoxy-naphthalen-2-yl)-acetic acid ethyl ester | 95361-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(Z)-Hydroxyimino]-(6-methoxy-naphthalen-2-yl)-acetic acid ethyl ester
• 英文别名: Ethyl alpha-hydroxyimino-6-methoxynaphth-2-ylacetate；ethyl 2-hydroxyimino-2-(6-methoxynaphthalen-2-yl)acetate
• CAS: 95361-31-2
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: ZCRVFQQUMMQYSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(Z)-Hydroxyimino]-(6-methoxy-naphthalen-2-yl)-acetic acid ethyl ester 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 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 30.0h， 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：

  2-萘甲醚 在 正丁基锂 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 [(Z)-Hydroxyimino]-(6-methoxy-naphthalen-2-yl)-acetic acid ethyl ester
  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

• Naphthylglycyl cephalosporin derivatives
  申请人：Eli Lilly and Company

  公开号：US04490370A1

  公开（公告）日：1984-12-25

  Naphthylglycyl and tetrahydronaphthylglycyl cephalosporins are potent antibacterial agents and are particularly useful as oral treatments for upper respiratory infections.

  Naphthylglycyl和tetrahydronaphthylglycyl头孢菌素是强效的抗菌剂，特别适用于口服治疗上呼吸道感染。
• Improvements in or relating to naphthylglycyl cephalosporin derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0122155A2

  公开（公告）日：1984-10-17

  Naphthylglycyl and tetrahydronaphthylglycyl cephalosporins are potent antibacterial agents and particularly useful in the oral treatment of upper respiratory infections.

  萘乙酰基和四氢萘乙酰基头孢菌素是强效抗菌剂，尤其适用于口服治疗上呼吸道感染。
• US4490370A
  申请人：——

  公开号：US4490370A

  公开（公告）日：1984-12-25