3-(2-(2-phenylethyl)benzimidazol-4-yl)-3-hydroxypropanoic acid | 201411-49-6

• 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: 3-(2-(2-phenylethyl)benzimidazol-4-yl)-3-hydroxypropanoic acid
• 英文别名: 3-hydroxy-3-[2-(2-phenylethyl)-1H-benzimidazol-4-yl]propanoic acid
• CAS: 201411-49-6
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: NBDFAOVIPWQHHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  86.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 3-hydroxy-3-[2-(2-phenylethyl)benzoimidazol-4-yl]propanoate 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.67h， 以66%的产率得到3-(2-(2-phenylethyl)benzimidazol-4-yl)-3-hydroxypropanoic acid
  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

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。
• Aryl hydrocarbon receptor (AhR) modifiers as novel cancer therapeutics
  申请人：Trustees of Boston University

  公开号：US10258600B2

  公开（公告）日：2019-04-16

  Provided herein are novel agents that modulate AhR activity for use in therapeutic compositions and methods thereof for inhibiting cancer cell proliferation and tumor cell invasion and metastasis. The agents comprise AhR inhibitors or non-constitutive AhR agonists of Formula (I) and (II) for the inhibition of cancer cell growth and parameters that characterize tumor metastasis, such as tumor cell invasiveness.

  本文提供了调节 AhR 活性的新型制剂，用于抑制癌细胞增殖和肿瘤细胞侵袭及转移的治疗组合物及其方法。这些制剂包括式（I）和式（II）的 AhR 抑制剂或非组成型 AhR 激动剂，用于抑制癌细胞生长和表征肿瘤转移的参数，如肿瘤细胞侵袭性。
• BENZIMIDAZOLE DERIVATIVES
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP0936218B1

  公开（公告）日：2003-04-02
• ARYL HYDROCARBON RECEPTOR (AHR) MODIFIERS AS NOVEL CANCER THERAPEUTICS
  申请人：Trustees of Boston University

  公开号：EP2598138A2

  公开（公告）日：2013-06-05
• SELECTIVE EXPANSION OF DIFFERENT SUBPOPULATIONS OF T CELLS BY THE ALTERATION OF CELL SURFACING SIGNALS AND SIGNAL RATIO
  申请人：Life Technologies AS

  公开号：EP3368659A1

  公开（公告）日：2018-09-05