2-氯-1-(2-苯基乙基)苯并咪唑 | 101953-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-氯-1-(2-苯基乙基)苯并咪唑
• 英文名称: 2-chloro-1-(2-phenylethyl)benzimidazole
• CAS: 101953-58-6
• 化学式: C₁₅H₁₃ClN₂
• 分子量: 256.735
• InChiKey: RIYHFXOUGPZLCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-氯-1-(2-苯基乙基)苯并咪唑 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 {[1-(2-phenylethyl)-1,3-dihydro-2H-benzimidazol-2-ylidene]hydrazono}(2-furyl)acetic acid
  参考文献：
  名称：

  3-Aryl-[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-one: A Novel Template for the Design of Highly Selective A_2B Adenosine Receptor Antagonists

  摘要：

  In an effort to identify novel ligands possessing high affinity and selectivity for the A(2B) AR subtype, we further investigated the class of 3-aryl[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-ones V, previously disclosed by us as selective A(1) AR antagonists. Preliminary assays on a number of triazinobenzimidazoles derived from our "in-house" collection revealed that all the derivatives selected showed significant affinity at A(2B) AR, no affinity at A(3) AR, and various degrees of selectivity toward A(1) and A(2A) ARs. Investigation of a new series featuring modified substituents at the 10-position (4'-chlorophenyl or phenylethyl groups), and a chlorine atom at the 7-position (X) of the triazinobenzimidazole nucleus, yielded highly potent and selective A(2B) AR antagonists. The presence of a pendant 3-phenyl ring appears to hamper the interaction with A(2A) AR, conferring high A(2B)/A(2A) AR selectivity. Derivative 13 (X = Cl, R = C6H5) is the most potent and selective compound, with an IC50 of 3.10 nM at A(2B) AR and no affinity at A(1), A(2A), and A(3) ARs.

  DOI：

  10.1021/jm201177b
• 作为产物：
  描述：

  2-氯苯并咪唑 、 乙基溴苯 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以62%的产率得到2-氯-1-(2-苯基乙基)苯并咪唑
  参考文献：
  名称：

  合成作为H1抗组胺药的2-（4-取代-1-哌嗪基）苯并咪唑。

  摘要：

  制备了一系列的2-（4-取代的-1-（高）哌嗪基）苯并咪唑，并在体内和体外测试了H1-抗组胺活性。大多数化合物显示出抗组胺活性，而某些1- [2-（取代-氧基）乙基]衍生物则显示出有效的活性。在结构活性比较中，发现苯并咪唑核的1-位上的2-（取代-氧）乙基中的氧原子对于有效的抗组胺活性，特别是在体内具有重要作用。最有效的化合物之一1-（2-乙氧基乙基）-2-（4-甲基-1-高哌嗪基）苯并咪唑（69）的体内H1抗组胺活性比马来酸氯苯那敏高39倍，因此被选作临床评估。

  DOI：

  10.1021/jm00157a010

文献信息

• 3-(Fur-2-yl)-10-(2-phenylethyl)-[1,2,4]triazino[4,3-<i>a</i>]benzimidazol-4(10<i>H</i>)-one, a Novel Adenosine Receptor Antagonist with A_2A-Mediated Neuroprotective Effects
  作者：Alessia Scatena、Francesco Fornai、Maria Letizia Trincavelli、Sabrina Taliani、Simona Daniele、Isabella Pugliesi、Sandro Cosconati、Claudia Martini、Federico Da Settimo

  DOI：10.1021/cn200036s

  日期：2011.9.21

  In this study, compound FTBI (3-(2-furyl)-10-(2-phenylethyl)[1,2,4]triazino[4,3-a]benzimidazol-4(10H)-one) was selected from a small library of triazinobenzimidazole derivatives as a potent A(2A) adenosine receptor (AR) antagonist and tested for its neuroprotective effects against two different kinds of dopaminergic neurotoxins, 1-methyl-4-phenylpyridinium (MPP+) and methamphetamine (METH), in rat PC12 and in human neuroblastoma SH-SYSY cell lines. FTBI, in a concentration range corresponding to its affinity for A(2A) AR subtype, significantly increased the number of viable PC12 cells after their exposure to METH and, to a similar extent, to MPP+, as demonstrated in both trypan blue exclusion assay and in cytological staining. These neuroprotective effects were also observed with a classical A(2A) AR antagonist, ZM241385, and appeared to be completely counteracted by the AR agonist, NECA, supporting A(2A) ARs are directly involved in FTBI-mediated effects. Similarly, in human SH-SYSY cells, FTBI was able to prevent cell toxicity induced by MPP+ and METH, showing that this A(2A) AR antagonist has a neuroprotective effect independently by the specific cell model. Altogether these results demonstrate that the A(2A) AR blockade mediates cell protection against neurotoxicity induced by dopaminergic neurotoxins in dopamine containing cells, supporting the potential we of A(2A) AR antagonists in dopaminergic degenerative diseases including Parkinson's disease.
• 5-HT3R Binding of lerisetron: an interdisciplinary approach to drug–Receptor interactions
  作者：Harish S. Parihar、Asha Suryanarayanan、Chun Ma、Prasad Joshi、Padma Venkataraman、Marvin K. Schulte、Karen S. Kirschbaum

  DOI：10.1016/s0960-894x(01)00417-6

  日期：2001.8

  The design, synthesis, and use of lerisetron-based molecular probes to investigate the 5-HT3R binding site are described. A SAR study, which involved distance and electronic parameter modifications of lerisetron's N-benzyl group, resulted in the discovery of a partial agonist. (C) 2001 Elsevier Science Ltd. All rights reserved.
• IEMURA RYUICHI; KAWASHIMA TSUNEO; FUKUDA TOSHIKAZU; ITO KEIZO; TSUKAMOTO +, J. MED. CHEM., 29,(1986) N 7, 1178-1183
  作者：IEMURA RYUICHI、 KAWASHIMA TSUNEO、 FUKUDA TOSHIKAZU、 ITO KEIZO、 TSUKAMOTO +

  DOI：——

  日期：——