5-(3-bromophenyl)-2-trityltetrazole | 143722-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-(3-bromophenyl)-2-trityltetrazole
• 英文别名: 5-(3-Bromophenyl)-2-(triphenylmethyl)-2H-tetrazole
• CAS: 143722-26-3
• 化学式: C₂₆H₁₉BrN₄
• 分子量: 467.368
• InChiKey: LPLHXKBXUYIMDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3-bromophenyl)-2-trityltetrazole 、 硼酸三甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Structure-based optimization of cephalothin-analogue boronic acids as β-lactamase inhibitors

  摘要：

  Boronic acids have proved to be promising selective inhibitors of beta-lactamases, acting as transition state analogues. Starting from a previously described nanomolar inhibitor of AmpC beta-lactamase, three new inhibitors were designed to gain interactions with highly conserved residues, such as Asn343, and to bind more tightly to the enzyme. Among these, one was obtained by stereoselective synthesis and succeeded in placing its anionic group into the carboxylate binding site of the enzyme, as revealed by X-ray crystallography of the complex inhibitor/AmpC. Nevertheless, it failed at improving affinity, when compared to the lead from which it was derived. The origins of this structural and energetic discrepancy are discussed.

  DOI：

  10.1016/j.bmc.2007.10.075
• 作为产物：
  描述：

  三苯基氯甲烷 、 5-(3-溴苯基)-1H-四氮唑 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以100%的产率得到5-(3-bromophenyl)-2-trityltetrazole
  参考文献：
  名称：

  Structure-based optimization of cephalothin-analogue boronic acids as β-lactamase inhibitors

  摘要：

  Boronic acids have proved to be promising selective inhibitors of beta-lactamases, acting as transition state analogues. Starting from a previously described nanomolar inhibitor of AmpC beta-lactamase, three new inhibitors were designed to gain interactions with highly conserved residues, such as Asn343, and to bind more tightly to the enzyme. Among these, one was obtained by stereoselective synthesis and succeeded in placing its anionic group into the carboxylate binding site of the enzyme, as revealed by X-ray crystallography of the complex inhibitor/AmpC. Nevertheless, it failed at improving affinity, when compared to the lead from which it was derived. The origins of this structural and energetic discrepancy are discussed.

  DOI：

  10.1016/j.bmc.2007.10.075

文献信息

• Tetrazolylphenylboronic acid intermediates for the synthesis of A II receptor antagonists
  申请人：E.I. DUPONT DE NEMOURS AND COMPANY

  公开号：EP1384717A2

  公开（公告）日：2004-01-28

  Novel tetrazolylphenylboronic acids, methods for their preparation and methods for preparing biphenyltetrazole compounds which are angiotensin II receptor antagonists or which are useful intermediates to prepare angiotensin II receptor antagonists. An illustrative biphenyl tetrazole compound is 2-n-butyl-4-chloro-1-[2'-(tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol, potassium salt.

  新型四唑基苯基硼酸、其制备方法以及制备血管紧张素 II 受体拮抗剂或制备血管紧张素 II 受体拮抗剂的有用中间体的联苯四唑化合物的方法。 一种说明性联苯四唑化合物是 2-正丁基-4-氯-1-[2'-(四唑-5-基)-1,1'-联苯-4-基)甲基]-1H-咪唑-5-甲醇钾盐。
• TETRAZOLYLPHENYLBORONIC ACID INTERMEDIATES FOR THE SYNTHESIS OF AII RECEPTOR ANTAGONISTS
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0643704A1

  公开（公告）日：1995-03-22
• EP0643704A4
  申请人：——

  公开号：EP0643704A4

  公开（公告）日：1995-04-12
• 2-(2'-triphenylmethyl-2'H-tetrazol-5'-yl)phenylboronic acid intermediates for the synthesis of A II receptor antagonists
  申请人：E. I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP1384717B1

  公开（公告）日：2008-05-14
• US5130439A
  申请人：——

  公开号：US5130439A

  公开（公告）日：1992-07-14