2-{5,6-dichloro-2-[(o-chlorophenyl)methyl]-1,3-diaza-1H-inden-1-yl}-1-hydrazino-1-ethanone | 1443550-91-1

• 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-{5,6-dichloro-2-[(o-chlorophenyl)methyl]-1,3-diaza-1H-inden-1-yl}-1-hydrazino-1-ethanone
• 英文别名: 2-[5,6-dichloro-2-(2-chlorobenzyl)-1H-benzimidazol-1-yl]acetic acid hydrazide；5,6-Dichloro-2-(2-chlorobenzyl)-1h-benzimidazol-1-acetic acid hydrazide；2-[5,6-dichloro-2-[(2-chlorophenyl)methyl]benzimidazol-1-yl]acetohydrazide
• CAS: 1443550-91-1
• 化学式: C₁₆H₁₃Cl₃N₄O
• 分子量: 383.664
• InChiKey: VBDBJKROIHVKEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 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：
  72.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二茂铁甲醛 、 2-{5,6-dichloro-2-[(o-chlorophenyl)methyl]-1,3-diaza-1H-inden-1-yl}-1-hydrazino-1-ethanone 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.12h， 以33%的产率得到1-[(E)-ferrocenylmethylidenehydrazino]-2-{5,6-dichloro-2-[(o-chlorophenyl)methyl]-1,3-diaza-1H-inden-1-yl}-1-ethanone
  参考文献：
  名称：

  Acetate bridged dinuclear Cu(II) complexes with ferrocene based benzimidazol ligands: Synthesis, spectroscopy, electrochemistry, DFT calculations and catecholase activity

  摘要：

  Two new benzimidazole ligands, 1-[(E)-ferrocenylmethylidenehydrazino]-2-{5,6-dichloro-2-[(o-chloro-phenyl)methyl]-1,3-diaza-1H-inden-1-yl}-1-ethanone (1) and 1-[(E)-ferrocenylmethylidenehydrazino]-2-{2-[p-(trifluoromethyl)phenyl]-1,3-diaza-1H-inden-1-yl}-1-ethanone (2), and their copper(II) complexes (1a, 2a) have been prepared and characterized by IR, UVVis, NMR, TG/DTA and MALDI-TOF mass spectrometry. DFT-based molecular orbital energy calculations and the electrochemical behavior of the compounds have been also studied to explain the redox potentials of the compounds. The catecholase-mimetic activities of the complexes have been investigated by monitoring the formation of 3,5-di-tert-butyl-benzoquinone from 3,5-di-tert-butylcatechol. The catalytic activity of 1a is slightly lower than that of 2a, and the correlation between catalytic activity and electrochemical behaviors of the compounds has been established. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.03.017
• 作为产物：
  描述：

  5,6-dichloro-2-(2-chlorobenzyl)-1H-benzimidazole 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 0.2h， 生成 2-{5,6-dichloro-2-[(o-chlorophenyl)methyl]-1,3-diaza-1H-inden-1-yl}-1-hydrazino-1-ethanone
  参考文献：
  名称：

  通过微波技术有效合成苯并咪唑及其生物活性

  摘要：

  摘要为合成苯并咪唑开发了一种简单实用的方案。该方案使用亚氨基酯盐酸盐，其在微波辐射下与4,5-二氯-1,2-苯二胺的反应中非常有用，可得到产率高且反应时间短的产物。该方法可以用作合成苯并咪唑的通用技术。评价合成的化合物的生物学特性，例如抗脂肪酶，抗病毒和抗肿瘤活性。尽管有低毒性，但五种苯并咪唑-1-乙酸酰肼在25μg/ cm 3浓度下仍显示出轻微的抗病毒活性。取代的2-苄基苯并咪唑类药物对腺癌（CT26）和黑色素瘤（B16F10）癌细胞的活性低于10μg/ cm 3。。其中六种化合物在不同浓度下均显示出抗脂肪酶的活性。一种化合物的IC 50值为0.35μg/ cm 3，与奥利司他（0.32μg/ cm 3）具有相似的活性。 图形概要

  DOI：

  10.1007/s00706-012-0916-0

文献信息

• An efficient synthesis of benzimidazoles via a microwave technique and evaluation of their biological activities
  作者：Bahittin Kahveci、Emre Menteşe、Musa Özil、Serdar Ülker、Murat Ertürk

  DOI：10.1007/s00706-012-0916-0

  日期：2013.7

  AbstractA simple and practical protocol was developed for the synthesis of benzimidazoles. The protocol uses iminoester hydrochloride which is very useful in the reaction with 4,5-dichloro-1,2-phenylenediamine under microwave irradiation leading to the products with good yields and in short reaction times. This method can be used as a general technique for synthesizing benzimidazoles. The synthesized compounds

  摘要为合成苯并咪唑开发了一种简单实用的方案。该方案使用亚氨基酯盐酸盐，其在微波辐射下与4,5-二氯-1,2-苯二胺的反应中非常有用，可得到产率高且反应时间短的产物。该方法可以用作合成苯并咪唑的通用技术。评价合成的化合物的生物学特性，例如抗脂肪酶，抗病毒和抗肿瘤活性。尽管有低毒性，但五种苯并咪唑-1-乙酸酰肼在25μg/ cm 3浓度下仍显示出轻微的抗病毒活性。取代的2-苄基苯并咪唑类药物对腺癌（CT26）和黑色素瘤（B16F10）癌细胞的活性低于10μg/ cm 3。。其中六种化合物在不同浓度下均显示出抗脂肪酶的活性。一种化合物的IC 50值为0.35μg/ cm 3，与奥利司他（0.32μg/ cm 3）具有相似的活性。 图形概要
• Acetate bridged dinuclear Cu(II) complexes with ferrocene based benzimidazol ligands: Synthesis, spectroscopy, electrochemistry, DFT calculations and catecholase activity
  作者：Kaan Karaoğlu、Mustafa Emirik、Emre Menteşe、Ali Zengin、Kerim Serbest

  DOI：10.1016/j.poly.2016.03.017

  日期：2016.6

  Two new benzimidazole ligands, 1-[(E)-ferrocenylmethylidenehydrazino]-2-5,6-dichloro-2-[(o-chloro-phenyl)methyl]-1,3-diaza-1H-inden-1-yl}-1-ethanone (1) and 1-[(E)-ferrocenylmethylidenehydrazino]-2-2-[p-(trifluoromethyl)phenyl]-1,3-diaza-1H-inden-1-yl}-1-ethanone (2), and their copper(II) complexes (1a, 2a) have been prepared and characterized by IR, UVVis, NMR, TG/DTA and MALDI-TOF mass spectrometry. DFT-based molecular orbital energy calculations and the electrochemical behavior of the compounds have been also studied to explain the redox potentials of the compounds. The catecholase-mimetic activities of the complexes have been investigated by monitoring the formation of 3,5-di-tert-butyl-benzoquinone from 3,5-di-tert-butylcatechol. The catalytic activity of 1a is slightly lower than that of 2a, and the correlation between catalytic activity and electrochemical behaviors of the compounds has been established. (C) 2016 Elsevier Ltd. All rights reserved.