2-(4-(4-cyanophenoxy)phenyl)-3H-benzo[d]imidazole-5-carbonitrile | 220955-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(4-(4-cyanophenoxy)phenyl)-3H-benzo[d]imidazole-5-carbonitrile
• 英文别名: 2-(4-(4-cyanophenoxy)phenyl)-1H-benzo[d]imidazole-6-carbonitrile；2-[4-(4-cyanophenoxy)phenyl]-3H-benzimidazole-5-carbonitrile
• CAS: 220955-77-1
• 化学式: C₂₁H₁₂N₄O
• 分子量: 336.352
• InChiKey: XNHXYYWWWGICAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-(4-cyanophenoxy)phenyl)-3H-benzo[d]imidazole-5-carbonitrile 以47%的产率得到
  参考文献：
  名称：

  TIDWELL R. R.; GERATZ J. D.; DANN O.; VOLZ G.; ZEH D.; LOEWE H., J. MED. CHEM., 1978, 21, NO 7, 613-623

  摘要：

  DOI：
• 作为产物：
  描述：

  5-cyano-2-(4-hydroxyphenyl)-3H-benzimidazole 以87%的产率得到
  参考文献：
  名称：

  TIDWELL R. R.; GERATZ J. D.; DANN O.; VOLZ G.; ZEH D.; LOEWE H., J. MED. CHEM., 1978, 21, NO 7, 613-623

  摘要：

  DOI：

文献信息

• 2-substituted phenyl-benzimidazole antibacterial agents
  申请人：Ortho Pharmaceutical Corporation

  公开号：US05942532A1

  公开（公告）日：1999-08-24

  The invention relates to benzimidazole antibacterial compounds of the Formula I: ##STR1## as described herein, pharmaceutical compositions containing the compounds, and methods for their production and use. These compounds are effective in inhibiting the action of a bacterial histidine protein kinase and are useful as anti-infective agents against a variety of bacterial organisms, including organisms which are resistant to other known antibiotics.

  本发明涉及化合物的苯并咪唑抗菌化合物的公式 I：如所述，含有这些化合物的药物组合物，以及它们的生产和使用方法。这些化合物在抑制细菌组氨酸蛋白激酶的作用方面是有效的，并且可用作抗感染剂，用于对抗各种细菌生物，包括对其他已知抗生素产生抗性的生物。
• Synthesis and Biological Evaluation of Botulinum Neurotoxin A Protease Inhibitors
  作者：Bing Li、Ramdas Pai、Steven C. Cardinale、Michelle M. Butler、Norton P. Peet、Donald T. Moir、Sina Bavari、Terry L. Bowlin

  DOI：10.1021/jm901852f

  日期：2010.3.11

  NSC 240898 was previously identified as a botulinum neurotoxin A light chain (BoNT/A LC) endopeptidase inhibitor by screening the National Cancer Institute Open Repository diversity set. Two types of analogues have been synthesized and shown to inhibit BoNT/A LC in a FRET-based enzyme assay, with confirmation in an HPLC-based assay. These two series of compounds have also been evaluated for inhibition of anthrax lethal factor (LF), an unrelated metalloprotease, to examine enzyme specificity of the BoNT/A LC inhibition. The most potent inhibitor against BoNT/A LC in these two series is compound 12 (IC50 = 2.5 mu M, FRET assay), which is 4.4-fold more potent than the lead structure and 11.2-fold more selective for BoNT/A LC versus the anthrax LF metalloproteinase. Structure-activity relationship studies have revealed structural features important to potency and enzyme specificity.
• Synthesis and Biological Evaluation of Inhibitors of Botulinum Neurotoxin Metalloprotease
  作者：Peter Wipf、Chenbo Wang、Julia Widom、Filip Petronijevic、James C. Burnett、Jonathan E. Nuss、Sina Bavari、Rick Gussio

  DOI：10.3987/com-08-s(d)8

  日期：——

  Based on the lead therapeutic agent NSC 240898, a new series of heterocyclic inhibitors of the BoNT serotype A metalloprotease has been generated. Highlights of the synthetic sequences include Sonogashira couplings of polysubstituted building blocks and gold-catalyzed indole formations. Preliminary structure-activity relationship studies afford detailed insights into the steric and electrostatic properties of the pharmacophore of this molecular scaffold.
• US5942532A
  申请人：——

  公开号：US5942532A

  公开（公告）日：1999-08-24
• [EN] 2-SUBSTITUTED PHENYL-BENZIMIDAZOLE ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTI-BACTERIENS DE 2-SUBSTITUTE PHENYL-BENZIMIDAZOLE
  申请人：ORTHO-MCNEIL PHARMACEUTICAL, INC.

  公开号：WO1999011627A1

  公开（公告）日：1999-03-11

  (EN) The invention relates to benzimidazole antibacterial compounds of formula (I) as described herein, pharmaceutical compositions containing the compounds, and methods for their production and use. These compounds are effective in inhibiting the action of a bacterial histidine protein kinase and are useful as anti-infective agents against a variety of bacterial organisms, including organisms which are resistant to other known antibiotics.(FR) Cette invention concerne des composés anti-bactériens à base de benzimidazole et répondant à la formule (I) telle que décrite dans le descriptif; des compositions pharmaceutiques renfermant ces composés; et des procédés permettant de les fabriquer et de les utiliser. Ces composés sont des inhibiteurs efficaces de l'action d'une protéine histidine kinase bactérienne et sont utilisés en tant qu'agents anti-infectieux agissant contre une série d'organismes bactériens, y compris les organismes résistant à d'autres antibiotiques connus.