4,6-dichloro-2-mercaptobenzimidazole | 99122-24-4

• 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: 4,6-dichloro-2-mercaptobenzimidazole
• 英文别名: 4,6-dichloro-1,3-dihydrobenzimidazole-2-thione
• CAS: 99122-24-4
• 化学式: C₇H₄Cl₂N₂S
• mdl: MFCD06336096
• 分子量: 219.094
• InChiKey: HNKJSTHUMPQTMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,6-dichloro-2-mercaptobenzimidazole 在 sodium hydroxide 、 双氧水 作用下， 生成 4,6-dichloro-1H-benzimidazole-2-sulfonic acid
  参考文献：
  名称：

  Benzimidazoles as NMDA Glycine-Site Antagonists: Study on the Structural Requirements in 2-Position of the Ligand

  摘要：

  A series of different substituted benzimidazole derivatives has been synthesized and evaluated for the ability to displace [3H]MDL-105,519 to rat cortical membranes. Two benzimidazole-2-carboxylic acids 9 b and 9 c, in this substitution pattern not yet described as glycine antagonists, showed IC50 values of 0.89 microM (9 b) and 38.0 microM (9 c). Replacement of the carboxylate function in 2-position by a sulfonic acid moiety appreciably increased solubility, but decreased the affinity giving evidence for the strong need of the carboxylate group within the ligand. Further structure-activity studies using benzimidazole-2-one derivatives with an acetic acid moiety adjacent to a ring nitrogen revealed new insights into the importance of amide functionalities within the heterocycle for the affinity of antagonist glycine-site ligands.

  DOI：

  10.1002/(sici)1521-4184(20005)333:5<123::aid-ardp123>3.0.co;2-5
• 作为产物：
  描述：

  二硫化碳 、 2,4-二氯-6-硝基苯胺 在 镍 氢氧化钾 、 一水合肼 作用下， 生成 4,6-dichloro-2-mercaptobenzimidazole
  参考文献：
  名称：

  Bindal, Varinder; Pujari, H. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 532 - 534

  摘要：

  DOI：

文献信息

• Synthesis and antimycobacterial activity of 2-substituted halogenobenzimidazoles
  作者：Z. Kazimierczuk、M. Andrzejewska、J. Kaustova、V. Klimešova

  DOI：10.1016/j.ejmech.2004.10.004

  日期：2005.2

  A series of substituted 2-polyfluoroalkyl and 2-nitrobenzylsulphanyl benzimidazoles was synthesized. The compounds were evaluated for their activity against four Mycobacterium strains; the activities were expressed as the minimum inhibitory concentration (MIC). The substances tested showed appreciable antimycobacterial activity, particularly 5,6-dichloro-2-nonafluorobutylbenzimidazole (2h), and 5-halogeno-(5a-c) and 4,6-dihalogeno- (5d and 5g) 2-(3,5-dinitrobenzylsulphanyl)benzimidazoles, whose MIC values for Mycobacterium kansasii and Mycobacterium avium exceeded that of isoniazide that was used as a reference compound. Relationships between structure and biological activity of the tested benzimidazole derivatives are discussed. (C) 2004 Elsevier SAS. All rights reserved.
• Synthesis, and antiprotozoal and antibacterial activities of S-substituted 4,6-dibromo- and 4,6-dichloro-2-mercaptobenzimidazoles
  作者：Mariola Andrzejewska、Lilian Yepez-Mulia、Amparo Tapia、Roberto Cedillo-Rivera、Agnieszka E. Laudy、Bohdan J. Starościak、Zygmunt Kazimierczuk

  DOI：10.1016/j.ejps.2003.10.024

  日期：2004.2

  The synthesis and some germicidal activities in vitro of two congener series of S-substituted 4,6-dihalogeno-2-mercapto-1H-benzimidazoles are reported. There was no substantial difference between antibacterial activities of corresponding 4,6-dichloro- and 4,6-dibromo-derivatives. The present results confirm lower susceptibility to substituted benzimidazoles of Gram-negative compared to Gram-positive bacteria. Minimum inhibitory concentrations (MICs) of a majority of the novel derivatives ranged between 25 and 100 mug/ml for Gram-positive bacteria. The most active compounds (MICs for Gram-positive bacteria: 0.78-50 mug/ml) were 4,6-dichloro-2-(4-nitrobenzylthio)-1H-benzimidazole and 4,6-dibromo-2-(4-nitrobenzylthio)-1H-benzimidazole that were 4-32 times more potent than nitrofurantoin against all Gram-positive bacteria utilized but Escherichia faecalis, against which they were, respectively, 2 and 4 times less potent than nitrofurantoin. Among Gram-negative bacteria used, Stenotrophomonas maltophilia and Bordetella bronchiseptica were most sensitive (as evidenced by a number of MICs less than or equal to 100 mug/ml), whereas Pseudomonas aeruginosa was most resistant to the new benzimidazole derivatives (all MICs > 400 mug/ml). All the new compounds were at least several times more active against Giardia intestinalis (IC50: 0.006-0.053 mug/ml), and a half of them were at least several times more active against Trichomonas vaginalis (IC50: 0.0015-0.182 mug/ml) than metronidazole (IC50: 0.210 and 0.037 mug/ml, respectively), the drug of choice in the treatment of G. intestinalis and T. vaginalis infections. (C) 2003 Elsevier B.V. All rights reserved.
• BINDAL, VARINDER;PUJARI, H., INDIAN J. CHEM., 26,(1987) N 6, 532-534
  作者：BINDAL, VARINDER、PUJARI, H.

  DOI：——

  日期：——
• COMPOUNDS, COMPOSITIONS COMPRSING SAME, AND METHODS RELATED THERETO
  申请人：UNIVERSITY OF IOWA RESEARCH FOUNDATION

  公开号：US20160115136A1

  公开（公告）日：2016-04-28

  Disclosed herein are compounds, such as benzimidazole derivatives, and composition, such as pharmaceutical compositions, and methods related thereto for treating or preventing microbial infections. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
• [EN] COMPOUNDS, COMPOSITIONS COMPRISING SAME, AND METHODS RELATED THERETO<br/>[FR] COMPOSÉS, COMPOSITIONS LES COMPRENANT ET PROCÉDÉS ASSOCIÉS
  申请人：UNIV IOWA RES FOUND

  公开号：WO2014160405A1

  公开（公告）日：2014-10-02

  Discloaed herein are compounds, such as benzimidazole derivatives, and composition, such as pharmaceutical compoistions, and methods related thereto for treating or preventing microbial infections. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.