tert-butyl 7α-<(methoxycarbonyl)amino>-3-(acetoxymethyl)-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate | 102253-57-6

• 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: tert-butyl 7α-<(methoxycarbonyl)amino>-3-(acetoxymethyl)-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate
• 英文别名: tert-butyl (6R,7S)-3-(acetyloxymethyl)-7-(methoxycarbonylamino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 102253-57-6
• 化学式: C₁₆H₂₂N₂O₇S
• 分子量: 386.426
• InChiKey: ICQQACNQLSWTBS-GXFFZTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 7α-<(methoxycarbonyl)amino>-3-(acetoxymethyl)-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到3-Acetoxymethyl-7-methoxycarbonylamino-5,5,8-trioxo-5lambda*6*-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
• 作为产物：
  描述：

  (6R,7S)-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 吡啶 、 吉拉尔特试剂 T 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl 7α-<(methoxycarbonyl)amino>-3-(acetoxymethyl)-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

文献信息

• Inhibition of human leukocyte elastase. 1. Inhibition by C-7-substituted cephalosporin tert-butyl esters
  作者：James B. Doherty、Bonnie M. Ashe、Peter L. Barker、Thomas J. Blacklock、John W. Butcher、Gilbert O. Chandler、M. Ellen Dahlgren、Philip Davies、Conrad P. Dorn

  DOI：10.1021/jm00171a028

  日期：1990.9

  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.