α-(8-chloro-2-naphthyl)-α-methoximinoacetic acid | 95361-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: α-(8-chloro-2-naphthyl)-α-methoximinoacetic acid
• 英文别名: alpha-Methoxyimino-alpha-(8-chloro-2-naphthyl)acetic acid；2-(8-chloronaphthalen-2-yl)-2-methoxyiminoacetic acid
• CAS: 95361-07-2
• 化学式: C₁₃H₁₀ClNO₃
• 分子量: 263.68
• InChiKey: YUIXDQWBBNFUTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-(8-chloro-2-naphthyl)-α-methoximinoacetic acid 在 亚磷酸三苯酯 、 氯 作用下， 以 二氯甲烷 为溶剂， 生成 (8-Chloro-naphthalen-2-yl)-[(Z)-methoxyimino]-acetyl chloride
  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：

  methylthio α-oxo-α-(8-chloro-2-napthyl)acetate 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 生成 α-(8-chloro-2-naphthyl)-α-methoximinoacetic 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

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。