2-(1-methyl-1H-imidazol-5-yl)-1H-benzo[d]imidazole | 953071-04-0

• 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-(1-methyl-1H-imidazol-5-yl)-1H-benzo[d]imidazole
• 英文别名: 2-(3-methylimidazol-4-yl)-1H-benzimidazole
• CAS: 953071-04-0
• 化学式: C₁₁H₁₀N₄
• 分子量: 198.227
• InChiKey: VNDRPKVURVIKJA-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198 °C
• 沸点：
  504.6±42.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-溴甲基-7,8-二氟-2(1H)-喹啉酮 、 2-(1-methyl-1H-imidazol-5-yl)-1H-benzo[d]imidazole 生成 7,8-difluoro-4-((2-(1-methyl-1H-imidazol-5-yl)-1H-benzo[d]-imidazol-1-yl)methyl)quinolin-2(1H)-one
  参考文献：
  名称：

  QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS

  摘要：

  本发明涉及式I的新型喹诺酮，其抑制可诱导型一氧化氮合酶，以及合成和使用该化合物的方法，包括通过给予该化合物治疗疾病的方法，用于抑制或调节一氧化氮合成和/或降低患者体内一氧化氮水平。

  公开号：

  US20080139558A1
• 作为产物：
  描述：

  N-甲基咪唑 、 2-溴苯并咪唑 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 N,N-dicyclohexyl-2-methyl-1-propanamine 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 以82%的产率得到2-(1-methyl-1H-imidazol-5-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  2-偶氮基自由基的光催化生成：中间体通过C–H官能团进行芳烃和杂芳烃的偶氮催化

  摘要：

  由2-溴唑通过光催化产生的2-偶氮基自由基是未修饰（杂）芳烃分子间芳基化的有力中间体。该反应的特征在于条件温和，操作简单，对官能团和空间要求高的基团的耐受性，范围广和抗Minisci选择性。提供了一种工作机制，并且低溶解度的胺对于成功偶联至关重要。该反应的实用性通过甲基雌酮的后期官能化和向其他溴代芳烃的应用证明。

  DOI：

  10.1021/acs.orglett.6b01718

文献信息

• IMIDAZOLE DERIVATIVES HAVING ARYL PIPERIDINE SUBSTITUENT, METHOD FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
  申请人：Suh Jee Hee

  公开号：US20100145054A1

  公开（公告）日：2010-06-10

  The present invention is directed to a novel imidazole derivative having an aryl piperidine substituent of formula (I) and a method for preparation thereof, and a pharmaceutical composition containing said imidazole derivative as an active ingredient for preventing or treating a MCH (melanine-concentrating hormone)-related disease.

  本发明涉及一种具有式(I)的芳基哌啶取代基的新型咪唑衍生物及其制备方法，以及含有该咪唑衍生物作为活性成分的药物组合物，用于预防或治疗与MCH（黑色素浓集激素）相关的疾病。
• Discovery of Dual Inducible/Neuronal Nitric Oxide Synthase (iNOS/nNOS) Inhibitor Development Candidate 4-((2-Cyclobutyl-1<i>H</i>-imidazo[4,5-<i>b</i>]pyrazin-1-yl)methyl)-7,8-difluoroquinolin-2(1<i>H</i>)-one (KD7332) Part 2: Identification of a Novel, Potent, and Selective Series of Benzimidazole-Quinolinone iNOS/nNOS Dimerization Inhibitors That Are Orally Active in Pain Models
  作者：Joseph E. Payne、Céline Bonnefous、Kent T. Symons、Phan M. Nguyen、Marciano Sablad、Natasha Rozenkrants、Yan Zhang、Li Wang、Nahid Yazdani、Andrew K. Shiau、Stewart A. Noble、Peter Rix、Tadimeti S. Rao、Christian A. Hassig、Nicholas D. Smith

  DOI：10.1021/jm100828n

  日期：2010.11.11

  Three isoforms of nitric oxide synthase (NOS), dimeric enzymes that catalyze the formation of nitric oxide (NO) from arginine, have been identified. Inappropriate or excessive NO produced by iNOS and/or nNOS is associated with inflammatory and neuropathic pain. Previously, we described the identification of a series of amide-quinolinone iNOS dimerization inhibitors that although potent, suffered from high clearance and limited exposure in vivo. By conformationally restricting the amide of this progenitor series, we describe the identification of a novel series of benzimidazole-quinolinone dual iNOS/nNOS inhibitors with low clearance and sustained exposure in vivo. Compounds were triaged utilizing an LPS challenge assay coupled with mouse and rhesus pharmacokinetics and led to the identification of 4,7-imidazopyrazine 42 as the lead compound. 42 (KD7332) (J. Med. Chem. 2009, 52, 3047-3062) was confirmed as an iNOS dimerization inhibitor and was efficacious in the mouse formalin model of nociception and Chung model of neuropathic pain, without showing tolerance after repeat dosing. Further 42 did not affect motor coordination up to doses or 1000 mg/kg, demonstrating a wide therapeutic margin.
• [EN] QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS<br/>[FR] QUINOLONES UTILES EN TANT QU'INHIBITEURS DE L'OXYDE NITRIQUE SYNTHASE INDUCTIBLE
  申请人：KALYPSYS INC

  公开号：WO2007117778A9

  公开（公告）日：2009-05-22
• US8198307B2
  申请人：——

  公开号：US8198307B2

  公开（公告）日：2012-06-12