methyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide | 104263-96-9

• 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: methyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide
• 英文别名: methyl 7α-methoxy-3-acetoxymethyl-3-cefem-4-carboxylate 1,1-dioxide；methyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 5,5-dioxide；3-Acetoxymethyl-7-methoxy-5,5,8-trioxo-5lambda*6*-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester；methyl (6R,7S)-3-(acetyloxymethyl)-7-methoxy-5,5,8-trioxo-5λ6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 104263-96-9
• 化学式: C₁₂H₁₅NO₈S
• 分子量: 333.319
• InChiKey: QZZSLQHZZRSQCE-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 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 dirhodium tetraacetate 、 sodium tungstate 、 18-冠醚-6 双氧水 、 碳酸氢钠 、 苯甲醚 、 三乙胺 、 三氟乙酸 、 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 219.0h， 生成 methyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide
  参考文献：
  名称：

  7α-烷氧基头孢菌素的改进立体特异性制备

  摘要：

  摘要 以 7-ACA 为原料制备了 7α-烷氧基-头孢菌素 1.1-二氧化物。关键步骤是 7β-氨基-头孢烯 5 与亚硝酸异戊酯的重氮化，然后是铑催化的交换反应，生成所需的 7α-烷氧基化合物。

  DOI：

  10.1080/00397919608003635

文献信息

• Inhibition of human leukocyte elastase. 2. Inhibition by substituted cephalosporin esters and amides
  作者：Paul E. Finke、Bonnie M. Ashe、Wilson B. Knight、Alan L. Maycock、Manuel A. Navia、Shrenik K. Shah、Kevan R. Thompson、Dennis J. Underwood、Hazel Weston

  DOI：10.1021/jm00171a029

  日期：1990.9

  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.
• 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：——
• An Improved Stereospecific Preparation of 7α-Alkoxycephalosporins
  作者：Szabolcs Sályi、László Tamás、Tamás E. Gunda、Ferenc Sztaricskai

  DOI：10.1080/00397919608003635

  日期：1996.2

  Abstract 7α-alkyloxy-cefalosporanate 1.1-dioxides were prepared starting from 7-ACA. The crucial step is the diazotation of the 7β-amino-cephem 5 with i-amylnitrite, followed by rhodium catalyzed exchange reaction to the desired 7α-alkoxy compounds.

  摘要 以 7-ACA 为原料制备了 7α-烷氧基-头孢菌素 1.1-二氧化物。关键步骤是 7β-氨基-头孢烯 5 与亚硝酸异戊酯的重氮化，然后是铑催化的交换反应，生成所需的 7α-烷氧基化合物。