3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5lambda*6*-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester | 95671-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5lambda*6*-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
• 英文别名: benzyl (6R,7S)-3-(acetyloxymethyl)-7-methoxy-5,5,8-trioxo-5λ6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 95671-92-4
• 化学式: C₁₈H₁₉NO₈S
• 分子量: 409.417
• InChiKey: HPXWKMYRUONXLH-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-氨基头孢烷酸 在 高氯酸 、 间氯过氧苯甲酸 、 亚硝酸异戊酯 作用下， 反应 36.5h， 生成 3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5lambda*6*-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 2. Inhibition by substituted cephalosporin esters and amides

  摘要：

  A variety of 7 alpha-methoxycephalosporin ester and amide sulfones were prepared and tested to determine the structure-activity relations for inhibition of human leukocyte elastase (HLE), a serine protease which has been implicated in several degenerative lung and tissue diseases. The most potent IC50 values were obtained with neutral, lipophilic derivatives, with the esters being more active than the amides. However, the best time-dependent inhibition in this series was observed with the p- and m-carboxybenzyl esters 7b and 7c. These results are discussed in terms of the proposed mechanism of inhibition as well as a molecular modeling study using the recently solved X-ray crystal structure of HLE.

  DOI：

  10.1021/jm00171a029

文献信息

• FINKE, PAUL E.;ASHE, BONNIE M.;KNIGHT, WILSON B.;MAYCOCK, ALAN L.;NAVIA, +, J. MED. CHEM., 33,(1990) N, C. 2522-2528
  作者：FINKE, PAUL E.、ASHE, BONNIE M.、KNIGHT, WILSON B.、MAYCOCK, ALAN L.、NAVIA, +

  DOI：——

  日期：——
• INTERLEUKIN CONVERTING ENZYME AND APOPTOSIS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0859779A1

  公开（公告）日：1998-08-26
• EP0859779A4
  申请人：——

  公开号：EP0859779A4

  公开（公告）日：2000-04-12
• [EN] INTERLEUKIN CONVERTING ENZYME AND APOPTOSIS<br/>[FR] ENZYME DE CONVERSION D'INTERLEUKINE ET APOPTOSE
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：WO1997008174A1

  公开（公告）日：1997-03-06

  (EN) The present invention is to the novel compounds of Formula (I), their pharmaceutical compositions, and to the novel inhibition of ICE and ICE-like proteins for use in the treatment of apoptosis, and disease states caused by excessive or inappropriate cell death.(FR) La présente invention concerne des composés représentés par la formule générale (I), leurs compositions pharmaceutiques. L'invention concerne également l'inhibition des protéines ICE et de type ICE convenant au traitement de l'apoptose ainsi qu'au traitement d'états pathologiques imputables à une mort cellulaire excessive ou inappropriée.