benzhydryl (2S,3S,5R)-6,6-dibromo-3-methyl-7-oxo-3-(triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | 125888-76-8

• 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: benzhydryl (2S,3S,5R)-6,6-dibromo-3-methyl-7-oxo-3-(triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 125888-76-8
• 化学式: C₂₃H₂₀Br₂N₄O₃S
• 分子量: 592.311
• InChiKey: KSTYNQWGQXTJIT-BWAGFHJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzhydryl (2S,3S,5R)-6,6-dibromo-3-methyl-7-oxo-3-(triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 在 potassium permanganate 、 叔丁基氯化镁 作用下， 以 二氯甲烷 为溶剂， 生成 benzhydryl (2S,3S,5R)-6-bromo-6-[(1R)-1-hydroxyethyl]-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C β-lactamases II

  摘要：

  Two stereoselective processes for the synthesis of novel 3,6-disubstituted penam sulfone derivatives were developed. One 6 beta-(l-hydroxyethyl) and four 6 beta-hydroxymethyl penam sulfone derivatives were synthesized. All four 6 beta-(hydroxymethyl)penam sulfone derivatives demonstrated good IC50 against both TEM-1 and AmpC beta-lactamases. of these, 6 beta-hydroxymethyl penam sulfone derivative 25 was the most active inhibitor which was able to restore the activity of piperacillin in vitro and in vivo against both TEM-1 and AmpC beta-lactamases producing organisms. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00107-9
• 作为产物：
  描述：

  2-(三甲基硅基)-1,2,3-三氮唑 、 6,6-dibromo-2,2-dimethylpenam-3-carboxylic acid 1-oxide diphenylmethyl ester 以 乙腈 为溶剂， 以20%的产率得到benzhydryl (2S,3S,5R)-6,6-dibromo-3-methyl-7-oxo-3-(triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C β-lactamases II

  摘要：

  Two stereoselective processes for the synthesis of novel 3,6-disubstituted penam sulfone derivatives were developed. One 6 beta-(l-hydroxyethyl) and four 6 beta-hydroxymethyl penam sulfone derivatives were synthesized. All four 6 beta-(hydroxymethyl)penam sulfone derivatives demonstrated good IC50 against both TEM-1 and AmpC beta-lactamases. of these, 6 beta-hydroxymethyl penam sulfone derivative 25 was the most active inhibitor which was able to restore the activity of piperacillin in vitro and in vivo against both TEM-1 and AmpC beta-lactamases producing organisms. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00107-9

文献信息

• Process for preparing 2-alpha-methyl-2-beta-(1,2,3-triazol-1-yl)methyl-penam-3-alpha-carboxylic acid derivatives
  申请人：TAIHO PHARMACEUTICAL COMPANY LIMITED

  公开号：EP0331395A1

  公开（公告）日：1989-09-06

  2α-Methyl-2β-(1,2,3-triazol-1-yl)methylpenam-3α-­carboxylic acid derivatives are prepared by reacting a penicillanic acid sulfoxide derivative of the formula wherein R is a penicillin carboxyl protecting group, and R₁ is hydrogen or halogen, R₂ is hydrogen, lower alkyl or the like with a triazole derivative of the formula wherein R₃ and R₄ are hydrogen, trialkylsilyl, lower alkyl, lower alkoxy or the like and R₅ is hydrogen or silyl substituted with 3 groups selected from the class consisting of lower alkyl, benzyl and phenyl in a solvent.

  2α-甲基-2β-(1,2,3-三唑-1-基)甲基-3α-吡喃-3α-羧酸衍生物的制备方法是将式中的青霉素亚砜衍生物与三唑衍生物反应 其中 R 是青霉素羧基保护基团，R₁ 是氢或卤素，R₂ 是氢、低级烷基或类似物与式中的三唑衍生物反应 其中 R₃ 和 R₄ 是氢、三烷基硅烷基、低级烷基、低级烷氧基或类似物，R₅ 是氢或在溶剂中被 3 个选自低级烷基、苄基和苯基的基团取代的硅烷基。
• US4895941A
  申请人：——

  公开号：US4895941A

  公开（公告）日：1990-01-23
• 6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C β-lactamases II
  作者：Panayota Bitha、Zhong Li、Gerardo D. Francisco、Youjun Yang、Peter J. Petersen、Eileen Lenoy、Yang-I Lin

  DOI：10.1016/s0960-894x(99)00107-9

  日期：1999.4

  Two stereoselective processes for the synthesis of novel 3,6-disubstituted penam sulfone derivatives were developed. One 6 beta-(l-hydroxyethyl) and four 6 beta-hydroxymethyl penam sulfone derivatives were synthesized. All four 6 beta-(hydroxymethyl)penam sulfone derivatives demonstrated good IC50 against both TEM-1 and AmpC beta-lactamases. of these, 6 beta-hydroxymethyl penam sulfone derivative 25 was the most active inhibitor which was able to restore the activity of piperacillin in vitro and in vivo against both TEM-1 and AmpC beta-lactamases producing organisms. (C) 1999 Elsevier Science Ltd. All rights reserved.