N-Benzoylaminomethanborsaeure | 64577-65-7

• 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: N-Benzoylaminomethanborsaeure
• 英文别名: benzamidomethylboronic acid
• CAS: 64577-65-7
• 化学式: C₈H₁₀BNO₃
• mdl: MFCD09032253
• 分子量: 178.983
• InChiKey: WMIKIKOIDGVEQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-((1S,2S,6R,8S)-2,9,9-Trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-ylmethyl)-benzamide 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-Benzoylaminomethanborsaeure
  参考文献：
  名称：

  Synthesis and Structural Investigation of Internally Coordinated α-Amidoboronic Acids

  摘要：

  Six new N-acyl-boroGly derivatives, along with their N-acyl-boroSar analogues, have been synthesized by modification of conventional procedures. Structural characterization of these alpha-amidoboronic acids was accomplished by extensive use of B-11 and H-1 NMR spectroscopy. These compounds were prepared to determine the extent of intramolecular B-O dative bond formation within the context of a five-membered (:O=C-N-C-B) ring motif. It is shown that the formation of such dative bonds depends on the nature of the substituents at both the acyl carbon and the nitrogen atoms. Computational evidence from second-order Moller-Plesset perturbation theory is provided in support of these findings.

  DOI：

  10.1021/jo051757h

文献信息

• Synthesis and evaluation of boronic acids as inhibitors of Penicillin Binding Proteins of classes A, B and C
  作者：Astrid Zervosen、André Bouillez、Alexandre Herman、Ana Amoroso、Bernard Joris、Eric Sauvage、Paulette Charlier、André Luxen

  DOI：10.1016/j.bmc.2012.04.018

  日期：2012.6

  In response to the widespread use of beta-lactam antibiotics bacteria have evolved drug resistance mechanisms that include the production of resistant Penicillin Binding Proteins (PBPs). Boronic acids are potent beta-lactamase inhibitors and have been shown to display some specificity for soluble transpeptidases and PBPs, but their potential as inhibitors of the latter enzymes is yet to be widely explored. Recently, a (2,6-dimethoxybenzamido) methylboronic acid was identified as being a potent inhibitor of Actinomadura sp. R39 transpeptidase (IC50: 1.3 mu M). In this work, we synthesized and studied the potential of a number of acylaminomethylboronic acids as inhibitors of PBPs from different classes. Several derivatives inhibited PBPs of classes A, B and C from penicillin sensitive strains. The (2-nitrobenzamido) methylboronic acid was identified as a good inhibitor of a class A PBP (PBP1b from Streptococcus pneumoniae, IC50 = 26 mu M), a class B PBP (PBP2xR6 from Streptococcus pneumoniae, IC50 = 138 mu M) and a class C PBP (R39 from Actinomadura sp., IC50 = 0.6 mu M). This work opens new avenues towards the development of molecules that inhibit PBPs, and eventually display bactericidal effects, on distinct bacterial species. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and Structural Investigation of Internally Coordinated α-Amidoboronic Acids
  作者：Jack H. Lai、Yuxin Liu、Wengen Wu、Yuhong Zhou、Hlaing H. Maw、William W. Bachovchin、Krishna L. Bhat、Charles W. Bock

  DOI：10.1021/jo051757h

  日期：2006.1.1

  Six new N-acyl-boroGly derivatives, along with their N-acyl-boroSar analogues, have been synthesized by modification of conventional procedures. Structural characterization of these alpha-amidoboronic acids was accomplished by extensive use of B-11 and H-1 NMR spectroscopy. These compounds were prepared to determine the extent of intramolecular B-O dative bond formation within the context of a five-membered (:O=C-N-C-B) ring motif. It is shown that the formation of such dative bonds depends on the nature of the substituents at both the acyl carbon and the nitrogen atoms. Computational evidence from second-order Moller-Plesset perturbation theory is provided in support of these findings.