(2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester | 81324-43-8

• 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: (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester
• 英文别名: Benzhydryl 6,6-dibromopenicillinate sulfone；benzhydryl (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 81324-43-8
• 化学式: C₂₁H₁₉Br₂NO₅S
• 分子量: 557.26
• InChiKey: SHJHKUIJGZAZQV-QFBILLFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester 在 乙基溴化镁 作用下， 以86%的产率得到benzhydryl 6α-bromopenicillanate S,S-dioxide
  参考文献：
  名称：

  烯丙基和炔丙基取代的戊砜是通用的中间体，可合成新的β-内酰胺酶抑制剂。

  摘要：

  使用烯丙基戊基砜作为关键中间体制备了几种烯基衍生物。这些衍生物在C-6处具有β构型的异构体显示出对CcrA酶的有效活性。开发了制备炔丙基戊砜的新方法。通过该途径制备的大多数三唑对用于抑制测定法的所有三种代表性酶表现出良好的活性。

  DOI：

  10.1016/s0960-894x(01)00148-2
• 作为产物：
  描述：

  二苯基重氮甲烷 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 生成 (2S,5R)-6,6-dibromo-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid diphenylmethyl ester
  参考文献：
  名称：

  青霉素砜 C6 取代基的修饰，旨在提高抑制剂识别和功效

  摘要：

  通过合成和评估一系列系统的 6β-取代青霉素砜，评估了氢键供给取代基对 β-内酰胺酶抑制活性的重要性。

  DOI：

  10.1016/j.bmcl.2010.10.134

文献信息

• Dipolar Cycloaddition of Novel 6-(Nitrileoxidomethyl) Penam Sulfone:  An Efficient Route to a New Class of β-Lactamase Inhibitors
  作者：Vincent P. Sandanayaka、Youjun Yang

  DOI：10.1021/ol006256r

  日期：2000.10.1

  6-(Nitrileoxidomethyl) penam sulfone intermediate was prepared in a few steps starting from commercially available (+)-6-aminopenicillanic acid. This intermediate underwent smooth 1, 3-dipolar cycloaddition reactions with various alkenes and alkynes to give cycloadducts in moderate to good yields. By this new method, several potent beta-lactamase inhibitors were synthesized. The regio- and stereoselectivity

  从市售（+）-6-氨基青霉酸开始，通过几个步骤制备了6-（三乙氧基甲基）戊酰胺砜中间体。该中间体与各种烯烃和炔烃进行平滑的1、3偶极环加成反应，以中等至良好的产率得到环加合物。通过这种新方法，合成了几种有效的β-内酰胺酶抑制剂。还讨论了环加成过程的区域选择性和立体选择性。
• Process for debromination of dibromopenicillanic acid and derivatives
  申请人：PFIZER INC.

  公开号：EP0129360A1

  公开（公告）日：1984-12-27

  A process for the debromination of 6-monobromo- and 6,6-dibromopenicillanic acid, and various derivatives thereof, bythe action of a bisulfite salt. The debrominated compounds produced find various utilities, as beta-lactamase inhibitors useful in therapy in combination with known beta-lactam antibiotics, or as intermediates in the further synthesis of useful betalactam compounds.

  一种通过亚硫酸氢盐的作用使 6-单溴和 6,6-二溴青霉烷酸及其各种衍生物脱溴的工艺。生成的脱溴化合物有多种用途，可作为β-内酰胺酶抑制剂与已知的β-内酰胺抗生素联合使用，或作为进一步合成有用的β-内酰胺化合物的中间体。
• 6-(1-hydroxyalkyl)penam sulfone derivatives as inhibitors of class a and class C β-lactamases I
  作者：Panayota Bitha、Zhong Li、Gerardo D. Francisco、Beth A. Rasmussen、Yang-I Lin

  DOI：10.1016/s0960-894x(99)00106-7

  日期：1999.4

  Five 6-(1-hydroxyalkyl)penam sulfone derivatives and two 6-(hydroxymethyl)penams were synthesized for beta-lactamase inhibitor screens. The substituent effects and stereochemical requirements of 6 alpha- and 6 beta-(1-hydroxyalkyl) groups for the biological activity of penam sulfone derivatives were investigated. Of these substituents, only the 6 beta-hydroxymethyl group of 15 improved the activity of sulbactam against both TEM-1 and AmpC beta-lactamases. The sulfone moiety is required for the enhancement of the beta-lactamase inhibitory activity. 6 beta-Hydroxymethylsulbactam (15) was able to restore the activity of piperacillin in vitro and in vivo against various beta-lactamase producing microorganisms. (C) 1999 Elsevier Science Ctd. All rights reserved.
• Kang, Han-Young; Pae, Ae Nim; Cho, Yong Seo, Heterocycles, 1996, vol. 43, # 11, p. 2337 - 2342
  作者：Kang, Han-Young、Pae, Ae Nim、Cho, Yong Seo、Choi, Kyung Il、Koh, Hun Yeong、Chung, Bong Young

  DOI：——

  日期：——
• Stereoselective Preparation of 6-b-Bromopenicillanic Acid Derivatives
  作者：Irena Lukic

  DOI：10.3987/com-94-6898

  日期：——

  A new stereoselective method for the preparation of 6-beta-bromopenicillanates is described. It comprises the reaction of 6,6-dibromopenicillanates with silver nitrate in 2-propanol.