2-(4-(6-(4,5-dihydro-1H-imidazol-2-yl)benzo[b]thiophen-2-yl)-phenyl)-4,5-dihydro-1H-imidazole | 73819-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(4-(6-(4,5-dihydro-1H-imidazol-2-yl)benzo[b]thiophen-2-yl)-phenyl)-4,5-dihydro-1H-imidazole
• 英文别名: 2-[2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]benzothiophen-6-yl]-4,5-dihydro-1H-imidazole；1H-Imidazole, 4,5-dihydro-2-(4-(6-(4,5-dihydro-1H-imidazol-2-yl)benzo(b)thien-2-yl)phenyl)-；2-[4-[6-(4,5-dihydro-1H-imidazol-2-yl)-1-benzothiophen-2-yl]phenyl]-4,5-dihydro-1H-imidazole
• CAS: 73819-21-3
• 化学式: C₂₀H₁₈N₄S
• 分子量: 346.456
• InChiKey: XEZBSEOSEVYUJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-Cyan-2-<4'-cyan-phenyl>-thionaphthen 、 乙二胺 在 tetraphosphorus decasulfide 作用下， 反应 2.0h， 以87%的产率得到2-(4-(6-(4,5-dihydro-1H-imidazol-2-yl)benzo[b]thiophen-2-yl)-phenyl)-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Botulinum Neurotoxin A Protease Inhibitors

  摘要：

  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.

  DOI：

  10.1021/jm901852f

文献信息

• BACTERIAL EFFLUX PUMP INHIBITORS FOR THE TREATMENT OF OPHTHALMIC AND OTIC INFECTIONS
  申请人：Bostian Keith

  公开号：US20080132457A1

  公开（公告）日：2008-06-05

  Efflux pump inhibitors are co-administered with antimicrobial agents for the treatment of ophthalmic or otic infections. The agents may be co-administered directly to the site of infection (e.g., the eye or ear).

  流出泵抑制剂与抗微生物药物一起联合使用，用于治疗眼科或耳科感染。这些药物可以直接共同应用于感染部位（例如眼睛或耳朵）。
• BROAD SPECTRUM ANTIBACTERIAL COMPOUNDS
  申请人：United States Government As Represented By The Secretary of The United States Army And The U.S. Army Medical Research & Materiel Command

  公开号：EP1945209B1

  公开（公告）日：2018-05-30
• US7947741B2
  申请人：——

  公开号：US7947741B2

  公开（公告）日：2011-05-24
• US7994225B2
  申请人：——

  公开号：US7994225B2

  公开（公告）日：2011-08-09
• 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.