2H-苯并咪唑-2-硫酮,4,6-二溴-1,3-二氢- | 116485-01-9

• 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: 2H-苯并咪唑-2-硫酮,4,6-二溴-1,3-二氢-
• 英文名称: 4,6-dibromo-2-thiobenzimidazole
• 英文别名: 4,6-dibromo-1,3-dihydrobenzimidazole-2-thione
• CAS: 116485-01-9
• 化学式: C₇H₄Br₂N₂S
• 分子量: 307.996
• InChiKey: JZGOLAQUSVAEDG-UHFFFAOYSA-N

物化性质

• 熔点：
  290 °C
• 沸点：
  357.8±52.0 °C(Predicted)
• 密度：
  2.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：

  2H-苯并咪唑-2-硫酮,4,6-二溴-1,3-二氢- 在 sodium hydroxide 、 双氧水 作用下， 生成 4,6-dibromo-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：

  2,4-二溴-6-硝基苯胺 在 镍 一水合肼 作用下， 生成 2H-苯并咪唑-2-硫酮,4,6-二溴-1,3-二氢-
  参考文献：
  名称：

  Sharma, B. R.; Pujari, H. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 121 - 127

  摘要：

  DOI：

文献信息

• Synthesis, antiprotozoal and anticancer activity of substituted 2-trifluoromethyl- and 2-pentafluoroethylbenzimidazoles
  作者：M Andrzejewska

  DOI：10.1016/s0223-5234(02)01421-6

  日期：2002.12.1

  The synthesis of several halogenated benzimidazoles substituted in position 2 with trifluoromethyl, pentafluoroethyl and 2-thioethylaminodimethyl group is reported. Antiprotozoal and anticancer activity of series of newly synthesized and previously obtained compounds was studied. All of tested bezimidazoles showed remarkable antiprotozoal activity against Giardia intestinalis, Entamoeba histolytica

  报道了在位置2处被三氟甲基，五氟乙基和2-硫代乙基氨基二甲基取代的几种卤代苯并咪唑的合成。研究了一系列新合成和先前获得的化合物的抗原生动物和抗癌活性。所有测试的苯并咪唑均对原肠贾第虫，溶组织性变形杆菌和阴道毛滴虫具有显着的抗原生动物活性。在所研究的卤代苯并咪唑类化合物中，最具抗癌活性的是5,6-二氯-2-五氟乙基化合物，尤其是针对乳腺癌和前列腺癌细胞系。
• 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.
• SHARMA, B. R.;PUJARI, H. K., INDIAN J. CHEM. B, 27,(1988) N 2, C. 121-127
  作者：SHARMA, B. R.、PUJARI, H. K.

  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.