tert-butyl 3-(acetoxymethyl)-7α-amino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate | 102253-55-4

• 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 3-(acetoxymethyl)-7α-amino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate
• 英文别名: 3-acetoxymethyl-7β-amino-3-cephem-4-carboxylic acid tert.-butyl ester；tert-butyl 7β-amino-3-acetoxymethyl-3-cephem-4-carboxylate；t-butyl 7β-amino-3-acetoxymethyl-3-cephem-4-carboxylate；tert-butyl 3-(acetoxymethyl)-7α-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；t-Butyl 7alpha-amino-3-acetoxymethyl-3-cephem-4-carboxylate；tert-butyl (6R,7S)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 102253-55-4
• 化学式: C₁₄H₂₀N₂O₅S
• 分子量: 328.389
• InChiKey: SKVHPNQACYIQDC-JOYOIKCWSA-N

物化性质

• 沸点：
  506.2±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(acetoxymethyl)-7α-amino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 (6R,7S)-3-Acetoxymethyl-7-formylamino-5,5,8-trioxo-5λ⁶-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 吉拉尔特试剂 T 作用下， 以 甲醇 为溶剂， 反应 1.67h， 以96%的产率得到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

文献信息

• Aminoethyl-methoxy-cephalosporin compounds
  申请人：Ciba-Geigy Corporation

  公开号：US04234578A1

  公开（公告）日：1980-11-18

  6.beta.-(R.sub.a)(R.sub.b)N-methylaryl-acetylamino-6.alpha.-methoxy-2,2-dim ethylpenam-3-carboxylic acid compounds and 7.beta.-(R.sub.a)(R.sub.b)N-methylaryl-acetylamino-7.alpha.-methoxy-3-ceph em-4-carboxylic acid compounds, wherein R.sub.a and R.sub.b independently of each other represent hydrogen or optionally substituted lower alkyl, or wherein R.sub.a and R.sub.b conjointly denote optionally substituted lower alkylene, wherein the aminomethyl-substituted aryl radical represents a corresponding thienyl, furyl or phenyl radical, and wherein the 3-position in 3-cephem compounds is unsubstituted or substituted by a modified hydroxyl group or an optionally substituted methyl group, exhibit antibiotic action against Gram-negative or Gram-positive micro-organisms.

  6-β-(R.sub.a)(R.sub.b)N-甲基芳基-乙酰氨基-6-α-甲氧基-2,2-二甲基佩纳姆-3-羧酸化合物和7-β-(R.sub.a)(R.sub.b)N-甲基芳基-乙酰氨基-7-α-甲氧基-3-头孢烯-4-羧酸化合物，其中R.sub.a和R.sub.b分别表示氢或可选择取代的较低烷基，或者R.sub.a和R.sub.b共同表示可选择取代的较低烷基，其中氨基甲基取代的芳基基团表示相应的噻吩基、呋喃基或苯基基团，3-头孢烯化合物中的3位位置未取代或被修改的羟基团或可选择取代的甲基团取代，对革兰氏阴性或革兰氏阳性微生物具有抗生素作用。
• 2-spirocyclopropyl cephalosporin sulfone derivatives
  申请人：SynPhar Laboratories, Inc.

  公开号：US05264429A1

  公开（公告）日：1993-11-23

  Derivatives of 2-spirocyclopropyl cephalosporin sulfone of the structural formula I ##STR1## are provided which are useful as potent elastase inhibitors.

  提供了2-螺环丙烷头孢菌素砜的衍生物，其结构式如下，可用作有效的弹性蛋白酶抑制剂。
• Cephem compounds and process for preparing the same
  申请人：Meiji Seika Kaisha Ltd.

  公开号：US04560750A1

  公开（公告）日：1985-12-24

  Disclosed is a novel cephem compound represented by the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and Y are as defined in the specification, which is a useful intermediate for synthesizing various cephalosporin antibiotics having a methoxy group at the 7.alpha.-position thereof. Also disclosed is a process for preparing the same.

  本发明揭示了一种新的头孢菌素化合物，其化学式为：##STR1## 其中R.sup.1、R.sup.2、R.sup.3、R.sup.4和Y如规范中所定义，它是合成具有7.alpha.-位置的甲氧基的各种头孢菌素类抗生素的有用中间体。同时还揭示了制备该化合物的方法。
• NOVEL 2-SPIROCYCLOPROPYL CEPHALOSPORIN SULFONE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：SYNPHAR LABORATORIES INC.

  公开号：EP0494914A1

  公开（公告）日：1992-07-22
• 2-SPIROCYCLOPROPYL CEPHALOSPORIN DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：SYNPHAR LABORATORIES INC.

  公开号：EP0494914B1

  公开（公告）日：1998-12-23