3-乙酰氧基甲基-7-氯-3-头孢烯-4-羧酸叔丁基酯 1,1-二氧化物 | 95672-01-8

• 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
• 中文名称: 3-乙酰氧基甲基-7-氯-3-头孢烯-4-羧酸叔丁基酯 1,1-二氧化物
• 中文别名: 3-乙酰氧基甲基-7-氯-3-头孢烯-4-羧酸叔丁基酯1,1-二氧化物
• 英文名称: tert-butyl 1,1-dioxo-trans-7-chloroacephalosporanate
• 英文别名: Amcccdb；tert-butyl (6R,7S)-3-(acetyloxymethyl)-7-chloro-5,5,8-trioxo-5λ6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 95672-01-8
• 化学式: C₁₄H₁₈ClNO₇S
• 分子量: 379.818
• InChiKey: QVPFKKWKDKAYSA-JOYOIKCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  24
• 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：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-乙酰氧基甲基-7-氯-3-头孢烯-4-羧酸叔丁基酯 1,1-二氧化物 、 二氯甲烷 、 盐酸二甲胺 、 聚合甲醛 在 二氯甲烷 、 水 、 Brine 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 以to give 1.6 g (81.6%) of t-butyl 7α-chloro-2-methylene-3-acetoxymethyl-3-cephem -4-carboxylate-1,1-dioxide, m.p. 148°-149° C的产率得到t-Butyl 7alpha-chloro-2-methylene-3-acetoxymethyl-3-cephem-4-carboxylate-1,1-dioxide
  参考文献：
  名称：

  2-spirocyclopropyl cephalosporin sulfone derivatives

  摘要：

  提供了2-螺环丙基头孢菌素磺酮(I结构式)的衍生物，这些衍生物是有用的强效弹性蛋白酶抑制剂。

  公开号：

  US05264429A1
• 作为产物：
  描述：

  7-氨基头孢烷酸 在 盐酸 、 sodium tungstate 、 亚硝酸异丙酯 、 硫酸 、 双氧水 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 93.08h， 生成 3-乙酰氧基甲基-7-氯-3-头孢烯-4-羧酸叔丁基酯 1,1-二氧化物
  参考文献：
  名称：

  A versatile synthesis of 1,1-dioxo 7-substituted cephems: preparation of the human leukocyte elastase (HLE) inhibitor 1,1-dioxo-trans-7-methoxycephalosporanic acid tert-butyl ester

  摘要：

  DOI：

  10.1021/jo00277a030

文献信息

• Synthesis and evaluation of new elastase inhibitors. I. 1,1-Dioxocephem-4-thiolesters
  作者：M Alpegiani、A Baici、P Bissolino、P Carminati、G Cassinelli、S Del Nero、G Franceschi、P Orezzi、E Perrone、V Rizzo、N Sacchi

  DOI：10.1016/0223-5234(92)90019-w

  日期：1992.12

  Several 7alpha-chloro and 7alpha-methoxy cephalosporin thiolester sulphones variously substituted at the C-3' position were synthesized from 7-amino-3-deacetoxycephalosporanic acid (7-ADCA). The compounds are time-dependent inhibitors of human leukocyte elastase (HLE) with effective K(i) ranging from micro- to nanomolar values, and second order rate constant reaching 10(6) M-1s-1; they also inhibit porcine pancreatic elastase with similar, though not identical efficiency. Compared to the corresponding cephem esters, the thiolesters of the 7-Cl series inhibit HLE up to 10 times as fast. Complete enzyme inactivation is achieved when a leaving group at C-3' (OAc or S-Het) is present, at the expense however of stability towards hydrolytic beta-lactam cleavage. In the 7-OMe series the thiolester compounds are far more stable and retain good efficiency for irreversible enzyme inhibition, superior to that displayed by the corresponding ester compounds. Three representative compounds (including one ester and two thiolesters) are shown to be effective inhibitors of HLE in the presence of insoluble elastin.
• 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.
• BLACKLOCK, THOMAS J.;BUTCHER, JOHN W.;SOHAR, PAUL;LAMANEC, THERESA ROTHAU+, J. ORG. CHEM., 54,(1989) N6, C. 3907-3913
  作者：BLACKLOCK, THOMAS J.、BUTCHER, JOHN W.、SOHAR, PAUL、LAMANEC, THERESA ROTHAU+

  DOI：——

  日期：——
• 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