(6R,7R)-3-Acetoxymethyl-7-{[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester | 81533-60-0

• 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: (6R,7R)-3-Acetoxymethyl-7-{[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
• CAS: 81533-60-0
• 化学式: C₂₁H₂₃N₃O₇S
• 分子量: 461.496
• InChiKey: WTBIYUPRVPTPHE-YRXBQWLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  128.41
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (6R,7R)-3-Acetoxymethyl-7-{[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 在 吉拉尔特试剂 T 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.92h， 生成 tert-butyl 3-(acetoxymethyl)-7α-amino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 1. Inhibition by C-7-substituted cephalosporin tert-butyl esters

  摘要：

  Time-dependent inhibitors of the enzyme human leukocyte elastase have been developed based on the cephem nucleus. A series of cephalosporin tert-butyl esters has been examined, and the activity of these compounds has been found to be very sensitive to C-7 substituents, with small, alpha-oriented, electron-withdrawing groups showing greatest activity. Additionally, the oxidation state of the sulfur atom has been found to play a role in potency, with sulfones showing considerably greater activity than the corresponding sulfides or beta-sulfoxides. The alpha-sulfoxides were inactive.

  DOI：

  10.1021/jm00171a028
• 作为产物：
  描述：

  对硝基苯甲醛 、 7-Aminocephalosporanic acid t-butyl ester 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以100%的产率得到(6R,7R)-3-Acetoxymethyl-7-{[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 1. Inhibition by C-7-substituted cephalosporin tert-butyl esters

  摘要：

  Time-dependent inhibitors of the enzyme human leukocyte elastase have been developed based on the cephem nucleus. A series of cephalosporin tert-butyl esters has been examined, and the activity of these compounds has been found to be very sensitive to C-7 substituents, with small, alpha-oriented, electron-withdrawing groups showing greatest activity. Additionally, the oxidation state of the sulfur atom has been found to play a role in potency, with sulfones showing considerably greater activity than the corresponding sulfides or beta-sulfoxides. The alpha-sulfoxides were inactive.

  DOI：

  10.1021/jm00171a028

文献信息

• Cephalosporin derivatives, processes for their preparation and compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0042232A2

  公开（公告）日：1981-12-23

  A compound of formula (I) or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof: wherein R is phenyl, 4-hydroxyphenyl, or a 5- or 6-membered heterocyclic ring containing up to three heteroatoms selected from oxygen, sulphur or nitrogen, optionally substituted with hydroxy, amino, halogen or C1-6 alkoxy; R' represents hydrogen or C1-6 alkyl; R2 and R3 are the same or different and rapresent hydrogen, C1-6 alkyl, halogen, amino, hydroxy, or C1-6 alkoxy; X represents oxygen or sulphur; and A represents hydrogen, pyridyl, acetoxy, carbamoyloxy or a heterocyclicthio group; Their preparation and use is described.

  式(I)化合物或其药学上可接受的盐或体内可水解的酯： 其中 R 是苯基、4-羟基苯基或含有最多三个选自氧、硫或氮的杂原子的 5 或 6 元杂环，可选择被羟基、氨基、卤素或 C1-6 烷氧基取代； R' 代表氢或 C1-6 烷基； R2 和 R3 相同或不同，代表 氢、C1-6 烷基、卤素、氨基、羟基或 C1-6 烷氧基； X 代表氧或硫；以及 A 代表氢、吡啶基、乙酰氧基、氨基甲酰氧基或杂环硫基； 说明了它们的制备和用途。
• US3988325A
  申请人：——

  公开号：US3988325A

  公开（公告）日：1976-10-26
• US4394375A
  申请人：——

  公开号：US4394375A

  公开（公告）日：1983-07-19