2-(2-Phenylethyl)benzimidazole-4-carboxylic acid | 201411-99-6

• 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-(2-Phenylethyl)benzimidazole-4-carboxylic acid
• 英文别名: 2-(2-phenylethyl)-1H-benzimidazole-4-carboxylic acid
• CAS: 201411-99-6
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: NZHCGYBWIXDCPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-Phenylethyl)benzimidazole-4-carboxylic acid 在 氯化亚砜 作用下， 反应 3.0h， 生成
  参考文献：
  名称：

  Characterization of the Antiallergic Drugs 3-[2-(2-Phenylethyl) benzoimidazole-4-yl]-3-hydroxypropanoic Acid and Ethyl 3-Hydroxy-3-[2-(2-phenylethyl)benzoimidazol-4-yl]propanoate as Full Aryl Hydrocarbon Receptor Agonists

  摘要：

  The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that mediates most of the toxic effects of numerous chlorinated (e.g., TCDD) and nonchlorinated polycyclic aromatic compounds (e.g., benzo[a]pyrene). Studies in AhR null mice suggested that this receptor may also play a role in the modulation of immune responses. Recently, two drugs, namely, M50354 and M50367 (ethyl ester derivative of M50354), were described as AhR ligands with high efficacy toward reducing atopic allergic symptoms in an AhR-dependent manner by skewing T helper cell differentiation toward a T(H)1 phenotype [Negishi et al. (2005) J. Immunol. 175 (11), 7348-7356]. Surprisingly, these drugs were shown to have minimal activity toward inducing classical dioxin responsive element-driven AhR-mediated CYP1A1 transcription. We synthesized and reevaluated the ability of these drugs to regulate AhR activity. In contrast to previously published data, both M50354 and M50367 were found to be potent inducers of several AhR target genes, namely, CYP1A1, CYP1B1, and UGT1A2. M50367 was a more effective agonist than M50354, perhaps accounting for its higher bioavailability in vivo. However, M50354 was capable of displacing an AhR-specific radioligand more effectively than M50367. This is consistent with M50354 being the active metabolite of M50367. In conclusion, two selective inhibitors of T(H)2 differentiation are full AhR agonists.

  DOI：

  10.1021/tx700350v
• 作为产物：
  描述：

  ethyl 2-(2-phenylethyl)benzimidazole-4-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 2-(2-Phenylethyl)benzimidazole-4-carboxylic acid
  参考文献：
  名称：

  Benzimidazole derivatives

  摘要：

  本发明提供了由公式(I)所表示的新型苯并咪唑衍生物;其制备方法;包含至少一种这样的化合物作为其活性成分的药物，特别是用于预防和/或治疗表现为嗜酸性粒细胞增多、支气管哮喘和过敏性疾病的药物;以及增强IFN-&ggr;产生的增强剂，特别是基于增强IFN-&ggr;产生作用的抗肿瘤剂或抗病毒剂，具有优异的口服生物利用度。

  公开号：

  US06387938B1

文献信息

• NOVEL BENZIMIDAZOLE DERIVATIVES
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP0936218A1

  公开（公告）日：1999-08-18

  Novel benzimidazole derivatives represented by general formula (I), a process for producing the same, and drugs containing as the active ingredient at least one of these compounds, in particular, preventives and/or remedies for diseases exhibiting acidophilia, bronchial asthma and allergic diseases, wherein R2 represents cyano, hydroxymethyl, 2-(2-imidazolyl)ethenyl, phenyl substituted by one or two -COOR3 groups, -COOR3 or -CONR4R5; A represents a group selected from the group consisting of -CO-, -CH(OR8)-, -CH2O-, -CH(NHR9)CH2-, -CH=CH- and -CH2CH2-; W represents -CH2- or a single bond; Q represents phenyl optionally substituted by a hydroxyl group; and n is from 0 to 2.

  由通式(I)代表的新型苯并咪唑衍生物，其生产工艺，以及含有至少一种这些化合物作为有效成分的药物，特别是预防和/或治疗嗜酸性疾病、支气管哮喘和过敏性疾病的药物，其中R2代表氰基、羟甲基、2-(2-咪唑基)乙烯基、被一个或两个-COOR3基团取代的苯基、-COOR3或-CONR4R5；A 代表选自-CO-、-CH(OR8)-、-CH2O-、-CH(NHR9)CH2-、-CH=CH- 和 -CH2CH2-的基团；W 代表-CH2-或单键；Q 代表任选被羟基取代的苯基；以及 n 为 0 至 2。
• BENZIMIDAZOLE DERIVATIVES
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP0936218B1

  公开（公告）日：2003-04-02
• US6387938B1
  申请人：——

  公开号：US6387938B1

  公开（公告）日：2002-05-14
• Characterization of the Antiallergic Drugs 3-[2-(2-Phenylethyl) benzoimidazole-4-yl]-3-hydroxypropanoic Acid and Ethyl 3-Hydroxy-3-[2-(2-phenylethyl)benzoimidazol-4-yl]propanoate as Full Aryl Hydrocarbon Receptor Agonists
  作者：José Luis Morales、Jacek Krzeminski、Shantu Amin、Gary H. Perdew

  DOI：10.1021/tx700350v

  日期：2008.2.1

  The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that mediates most of the toxic effects of numerous chlorinated (e.g., TCDD) and nonchlorinated polycyclic aromatic compounds (e.g., benzo[a]pyrene). Studies in AhR null mice suggested that this receptor may also play a role in the modulation of immune responses. Recently, two drugs, namely, M50354 and M50367 (ethyl ester derivative of M50354), were described as AhR ligands with high efficacy toward reducing atopic allergic symptoms in an AhR-dependent manner by skewing T helper cell differentiation toward a T(H)1 phenotype [Negishi et al. (2005) J. Immunol. 175 (11), 7348-7356]. Surprisingly, these drugs were shown to have minimal activity toward inducing classical dioxin responsive element-driven AhR-mediated CYP1A1 transcription. We synthesized and reevaluated the ability of these drugs to regulate AhR activity. In contrast to previously published data, both M50354 and M50367 were found to be potent inducers of several AhR target genes, namely, CYP1A1, CYP1B1, and UGT1A2. M50367 was a more effective agonist than M50354, perhaps accounting for its higher bioavailability in vivo. However, M50354 was capable of displacing an AhR-specific radioligand more effectively than M50367. This is consistent with M50354 being the active metabolite of M50367. In conclusion, two selective inhibitors of T(H)2 differentiation are full AhR agonists.
• Benzimidazole derivatives
  申请人：Mochida Pharmaceutical Co., Ltd.

  公开号：US06387938B1

  公开（公告）日：2002-05-14

  This invention provides novel benzimidazole derivatives represented by the formula (I); a process for producing the same; a drug containing at least one of such compounds as its active ingredient, in particular, a drug for preventing and/or treating diseases exhibiting eosinophilia, bronchial asthma and allergic diseases; and an enhancer for IFN-&ggr; production, and in particular, an antitumor agent or an antiviral agent based on the action of enhancing the IFN-&ggr; production which exhibits excellent oral bioavailability.

  本发明提供了由公式(I)所表示的新型苯并咪唑衍生物;其制备方法;包含至少一种这样的化合物作为其活性成分的药物，特别是用于预防和/或治疗表现为嗜酸性粒细胞增多、支气管哮喘和过敏性疾病的药物;以及增强IFN-&ggr;产生的增强剂，特别是基于增强IFN-&ggr;产生作用的抗肿瘤剂或抗病毒剂，具有优异的口服生物利用度。