5-(4,5-dihydro-1H-imidazol-2-yl)-2-(2-thiophen-2-yl-vinyl)-1H-benzoimidazole hydrochloride | 934708-79-9

• 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: 5-(4,5-dihydro-1H-imidazol-2-yl)-2-(2-thiophen-2-yl-vinyl)-1H-benzoimidazole hydrochloride
• 英文别名: E-6-(4,5-dihydro-1H-imidazol-2-yl)-2-(2-thiophen-2-ylvinyl)-3Hbenzimidazole hydrochloride；6-(4,5-dihydro-1H-imidazol-2-yl)-2-[(E)-2-thiophen-2-ylethenyl]-1H-benzimidazole;hydrochloride
• CAS: 934708-79-9
• 化学式: C₁₆H₁₄N₄S*ClH
• 分子量: 330.841
• InChiKey: UTFWWQHWYGABFG-CVDVRWGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  81.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4,5-dihydro-1H-imidazol-2-yl)-2-(2-thiophen-2-yl-vinyl)-1H-benzoimidazole hydrochloride 以 水 为溶剂， 反应 3.0h， 以65%的产率得到1,3-di-[5-(2-imidazolinyl)-2-benzoimidazolyl]-2,4-di-(2-thienyl)-cyclobutane dihydrochloride
  参考文献：
  名称：

  新型a基取代的苯并咪唑：化合物的合成和对二肽基肽酶III的抑制。

  摘要：

  二肽基肽酶III（DPP III），也称为脑啡肽酶B，是一种锌水解酶，在哺乳动物的疼痛调节系统中具有明确的作用。为了找到这种酶的有效拮抗剂，我们合成并筛选了少量苯并咪唑衍生物对其活性的影响。为了提高抑制潜力，将环丁烷环作为硬构象载体引入二mid基取代的二苯并咪唑。通过在水中进行光化学环化并遵循“绿色化学”方法的规则，从含有a基取代的苯并咪唑基团的环丁烷衍生物中，发现两种此类化合物（1'和4'）是强DPP III抑制剂， IC（50）值低于5 microM。化合物1'对人DPP III表现出时间依赖性抑制作用，其特征在于其二阶速率常数为6924 +/- 549 M（-1）min（-1）（K（i）= 0.20 microM）。肽底物valorphin通过1'保护酶免于失活。

  DOI：

  10.1016/j.bioorg.2006.11.002
• 作为产物：
  描述：

  3-(2-噻吩基)-2-丙烯醛 、 4-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,2-diamine hydrochloride 在 对苯醌 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以88%的产率得到5-(4,5-dihydro-1H-imidazol-2-yl)-2-(2-thiophen-2-yl-vinyl)-1H-benzoimidazole hydrochloride
  参考文献：
  名称：

  Novel Amidino-Substituted Thienyl- and Furylvinylbenzimidazole: Derivatives and Their Photochemical Conversion into Corresponding Diazacyclopenta[c]fluorenes. Synthesis, Interactions with DNA and RNA, and Antitumor Evaluation. 4

  摘要：

  Synthesis of novel nonfused amidino-substituted thienyl- and furyl vinylbenzimidazole: derivatives and their photochemical cyclization into corresponding diazacyclopenta[c]fluorenes is described. All studied compounds showed prominent growth inhibitor effect. The fused compounds showed stronger activity than nonfused ones, whereby imidazolyl-substituted compound 11 proved to be the most active one. Besides, it induced strong G2/M arrest of the cell cycle followed by drastic apoptosis, which is in accordance with the DNA intercalative binding mode determined by the spectroscopic studies. Nonfused derivatives induced strong S phase arrest of the cell cycle followed by apoptosis that together with DNA minor groove binding mode pointed to topoisomerase I inhibition. In addition, all nonfused compounds revealed pronounced selectivity toward tumor cells in comparison with nontumor cells. Oil the basis of the presented results, both nonfused and fused thiophene-containing, imidazolyl derivatives Should be considered as promising lead compounds for further investigation.

  DOI：

  10.1021/jm8000423

文献信息

• Novel Amidino-Substituted Thienyl- and Furylvinylbenzimidazole: Derivatives and Their Photochemical Conversion into Corresponding Diazacyclopenta[<i>c</i>]fluorenes. Synthesis, Interactions with DNA and RNA, and Antitumor Evaluation. 4
  作者：Marijana Hranjec、Ivo Piantanida、Marijeta Kralj、Lidija Šuman、Krešimir Pavelić、Grace Karminski-Zamola

  DOI：10.1021/jm8000423

  日期：2008.8.1

  Synthesis of novel nonfused amidino-substituted thienyl- and furyl vinylbenzimidazole: derivatives and their photochemical cyclization into corresponding diazacyclopenta[c]fluorenes is described. All studied compounds showed prominent growth inhibitor effect. The fused compounds showed stronger activity than nonfused ones, whereby imidazolyl-substituted compound 11 proved to be the most active one. Besides, it induced strong G2/M arrest of the cell cycle followed by drastic apoptosis, which is in accordance with the DNA intercalative binding mode determined by the spectroscopic studies. Nonfused derivatives induced strong S phase arrest of the cell cycle followed by apoptosis that together with DNA minor groove binding mode pointed to topoisomerase I inhibition. In addition, all nonfused compounds revealed pronounced selectivity toward tumor cells in comparison with nontumor cells. Oil the basis of the presented results, both nonfused and fused thiophene-containing, imidazolyl derivatives Should be considered as promising lead compounds for further investigation.
• Novel amidino-substituted benzimidazoles: Synthesis of compounds and inhibition of dipeptidyl peptidase III
  作者：Dejan Agić、Marijana Hranjec、Nina Jajčanin、Kristina Starčević、Grace Karminski-Zamola、Marija Abramić

  DOI：10.1016/j.bioorg.2006.11.002

  日期：2007.4

  dibenzimidazoles. Two such compounds (1' and 4') from the group of cyclobutane derivatives containing amidino-substituted benzimidazole moieties, obtained by photochemical cyclization in water and by respecting rules of the "green chemistry" approach, were found to be strong DPP III inhibitors, with IC(50) value below 5 microM. Compound 1' displayed time-dependent inhibition towards human DPP III, characterized

  二肽基肽酶III（DPP III），也称为脑啡肽酶B，是一种锌水解酶，在哺乳动物的疼痛调节系统中具有明确的作用。为了找到这种酶的有效拮抗剂，我们合成并筛选了少量苯并咪唑衍生物对其活性的影响。为了提高抑制潜力，将环丁烷环作为硬构象载体引入二mid基取代的二苯并咪唑。通过在水中进行光化学环化并遵循“绿色化学”方法的规则，从含有a基取代的苯并咪唑基团的环丁烷衍生物中，发现两种此类化合物（1'和4'）是强DPP III抑制剂， IC（50）值低于5 microM。化合物1'对人DPP III表现出时间依赖性抑制作用，其特征在于其二阶速率常数为6924 +/- 549 M（-1）min（-1）（K（i）= 0.20 microM）。肽底物valorphin通过1'保护酶免于失活。