2-Chloro-1-(3-cyano-benzyl)-1H-benzoimidazole | 714260-93-2

• 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-Chloro-1-(3-cyano-benzyl)-1H-benzoimidazole
• 英文别名: 3-[(2-chlorobenzimidazol-1-yl)methyl]benzonitrile
• CAS: 714260-93-2
• 化学式: C₁₅H₁₀ClN₃
• 分子量: 267.717
• InChiKey: KNVVBHIZBMELQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Chloro-1-(3-cyano-benzyl)-1H-benzoimidazole 、 4-氨基-1-[2-(4-甲氧基苯基)乙基]哌啶 在 potassium carbonate 作用下， 以 neat (no solvent) 为溶剂， 以15%的产率得到3-((2-((1-(4-methoxyphenethyl)piperidin-4-yl)amino)-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile
  参考文献：
  名称：

  阿司咪唑类似物的多级抗疟原虫活性和抑制血腥素形成为其作用方式的贡献者。

  摘要：

  利用药物重新定位方法衍生化阿司咪唑（AST），这是一种抗组胺药，其抗疟活性先前已在高通量筛选中确定。通过评估寄生虫的无性血液，肝脏和性配子分裂阶段，检查了其后类似物对疟原虫的生命周期的多阶段活性潜能。另外，对先前报道的血红素解毒对化合物作用方式的贡献进行了研究。17种衍生物中的10种对氯喹（CQ）敏感的恶性疟原虫NF54（PfNF54）菌株显示半数最大抑制浓度（IC50s）<0.1μM，同时对多药耐药菌株PfK1保持亚微摩尔效价，多数显示低与CQ交叉耐药的可能性。测试了选定的类似物（PfNF54-IC50 <0.1μM）对中国仓鼠卵巢（CHO）细胞的细胞毒性，发现其具有高度选择性（选择性指数> 100）。AST及其类似物针对配子体细胞的筛选显示了其对晚期恶性疟原虫配体细胞的中等活性（IC50：1-5μM），而对伯氏疟原虫肝阶段活性的评估则鉴定出一种化合物（3）的活性提高了3倍活性要比母体A

  DOI：

  10.1021/acsinfecdis.8b00272
• 作为产物：
  描述：

  3-[(2-oxo-3H-benzimidazol-1-yl)methyl]benzonitrile 在 三氯氧磷 作用下， 生成 2-Chloro-1-(3-cyano-benzyl)-1H-benzoimidazole
  参考文献：
  名称：

  Discovery of novel, orally available benzimidazoles as melanin concentrating hormone receptor 1 (MCHR1) antagonists

  摘要：

  Melanin concentrating hormone (MCH) is an important mediator of energy homeostasis and plays role in several disorders such as obesity, stress, depression and anxiety. The synthesis and biological evaluation of novel benzimidazole derivatives as MCHR1 antagonists are described. The in vivo proof of principle for weight loss with a lead compound from this series is exemplified. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.086

文献信息

• MEDICINAL USE OF RECEPTOR LIGANDS
  申请人：Receveur Jean-Marie

  公开号：US20090062317A1

  公开（公告）日：2009-03-05

  Compounds of formula (I) are ligands of the melanin concentrating hormone-1 receptor (MCH-1R), useful in the treatment of diseases responsive to modulation of melanin concentrating hormone (MCH) activity, for example feeding disorders and diseases for which obesity is a risk factor (I): wherein ring B is selected from specific substituted phenyl or benz-fused 5 membered N-containing heterocycles defined in the specification; R, is attached to a ring carbon of ring B, and represents hydrogen, F, Cl, or —OCH 3 ; X is ═CH— or ═N—; L, is —CH 2 — or —CH 2 CH 2 —; L 2 is a bond, —CH 2 — or —CO—; R2 is H or C, —C 3 alkyl, or —N(R 2 ) L, —is selected from specific cyclic amino linker radicals as defined in the specification; ring A is selected from specific N-containing heterocyclic rings as defined in the specification.

  式(I)的化合物是黑素浓集激素-1受体(MCH-1R)的配体，可用于治疗对黑素浓集激素(MCH)活性调节敏感的疾病，例如进食障碍和肥胖是危险因素的疾病（式(I)）：其中环B选自规定的特定取代苯基或苯并5元杂环；R附着在环B的环碳上，表示氢，F，Cl或—OCH3；X为═CH—或═N—；L为—CH2—或— —；L2为键，— —或—CO—；R2为H或C，—C3烷基，或—N(R2)L，—选自规定的特定环状氨基连接基团。环A选自规定的特定含氮杂环。
• [EN] MEDICINAL USE OF RECEPTOR LIGANDS<br/>[FR] UTILISATION MEDICALE DE LIGANDS RECEPTEURS
  申请人：7TM PHARMA AS

  公开号：WO2006010446A2

  公开（公告）日：2006-02-02

  Compounds of formula (I) are ligands of the melanin concentrating hormone-1 receptor (MCH-1 R), useful in the treatment of diseases responsive to modulation of melanin concentrating hormone (MCH) activity, for example feeding disorders and diseases for which obesity is a risk factor (I): wherein ring B is selected from specific substituted phenyl or benz-fused 5­membered N-containing heterocycles defined in the specification; R, is attached to a ring carbon of ring B, and represents hydrogen, F, Cl, or -OCH3; X is =CH- or =N-; L, is -CH2- or -CH2CH2- ; L2 is a bond, -CH2- or -CO-; R2 is H or C,-C3 alkyl, or -N(R2) L,- is selected from specific cyclic amino linker radicals as defined in the specification; ring A is selected from specific N- containing heterocyclic rings as defined in the specification.