p-nitrobenzyl 7--3-methyl-3-cephem-4-carboxylate | 95360-83-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: p-nitrobenzyl 7--3-methyl-3-cephem-4-carboxylate
• 英文别名: p-nitrobenzyl 7-[N-(tert-butoxycarbonyl)(6-methoxy-2-naphthyl)glycylamido]-3-methyl-3-cephem-4-carboxylate
• CAS: 95360-83-1
• 化学式: C₃₃H₃₄N₄O₉S
• 分子量: 662.72
• InChiKey: DSHGXNJMAFERBY-GFFRDVJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  47.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  166.41
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  p-nitrobenzyl 7--3-methyl-3-cephem-4-carboxylate 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、379.21 kPa 条件下， 反应 3.08h， 生成 (R)-7-<(6-methoxy-2-naphthyl)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：

  乙基(6-甲氧基-2-萘基)(氧代)乙酸酯 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 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 33.0h， 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