2-(5-nitrothiophen-2-yl)-1H-benzo[d]imidazole-5-carboxylic acid

• 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-nitrothiophen-2-yl)-1H-benzo[d]imidazole-5-carboxylic acid
• 英文别名: 1H-2-(5-nitrothiophen-2-yl)benzimidazole-5-carboxylic acid；2-(5-nitro-2-thienyl)-1H-benzimidazole-5-carboxylic acid；2-(5-nitrothiophen-2-yl)-3H-benzimidazole-5-carboxylic acid
• 化学式: C₁₂H₇N₃O₄S
• 分子量: 289.271
• InChiKey: XJAXFJREOVQGQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(5-nitrothiophen-2-yl)-1H-benzo[d]imidazole-5-carboxylic acid 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 48.5h， 生成 N'-(3,4-dimethoxybenzoyl)-(5-nitrothiophen-2-yl)-1H-benzo[d]imidazole-5-carbohydrazide
  参考文献：
  名称：

  Synthesis and biological evaluation of benzimidazole-5-carbohydrazide derivatives as antimalarial, cytotoxic and antitubercular agents

  摘要：

  A series of N'-substituted-2-(5-nitrofuran or 5-nitrothiophen-2-yl)-3H-benzo[d]imidazole-5-carbohydrazide derivatives were synthesized and investigated for their abilities to inhibit beta-hematin formation, hemoglobin hydrolysis and in vivo for their antimalarial efficacy in rodent Plasmodium berghei. Selected analogues were screened for their antitubercular activity against sensitive MTB H(37)Rv and multidrug-resistant MDR-MTB strains, and cytotoxic activity against a panel of human tumor cell lines and two non-tumourogenic cell lines. Compounds 3a, 5a, f, 6g were the most promising as inhibitors of beta-hematin formation, however, their effect as inhibitors of hemoglobin hydrolysis were marginal. The most active compounds to emerge from the in vitro and in vivo murine studies were 3a and 6i, suggesting an antimalarial activity via inhibition of beta-hematin formation and are as efficient as chloroquine. The cytotoxic and antitubercular activities of the present compounds were not comparable with those of the standard drugs employed. But, however, compound 5b showed better antitubercular activity compared to rifampin against multidrug-resistant MDR-MTB strains. Compounds 3a, 6i and 5b showed a good safety index. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.050
• 作为产物：
  描述：

  methyl 1H-2-(5-nitrothiophen-2-yl)benzimidazole-5-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以96.3%的产率得到2-(5-nitrothiophen-2-yl)-1H-benzo[d]imidazole-5-carboxylic acid
  参考文献：
  名称：

  Benzimidazole derivatives

  摘要：

  以下是化学式（I）表示的化合物及其药理学上可接受的盐，它们是一种新型化合物，可作为抗癌剂、抗病毒剂或抗微生物剂使用。

  公开号：

  US05852011A1

文献信息

• Synthesis, antimalarial, antiproliferative, and apoptotic activities of benzimidazole-5-carboxamide derivatives
  作者：Jesús A. Romero、María E. Acosta、Neira D. Gamboa、Michael R. Mijares、Juan B. De Sanctis、Ligia J. Llovera、Jaime E. Charris

  DOI：10.1007/s00044-018-2258-x

  日期：2019.1

  formation in vitro, and in vivo were tested as antimalarial against mice infected by a strain of Plasmodium berghei ANKA sensitive to chloroquine. The survival time was increased by the compounds 3a and 4d to 17.00 ± 1.26 and 20.20 ± 1.95 days, while the progress of the infection was reduced to 4.02 ± 0.45 and 3.05 ± 0.09, respectively. The cytotoxic activity of all these compounds was assessed against

  使用硝基苯作为氧化剂，获得N'-取代的-2-（5-硝基杂环-2-基）-3 H-苯并[d]咪唑-5-甲酰胺类型的28种化合物，从而获得苯并咪唑支架，使用Steglich酯化反应的改进方法获得最终化合物。测试了该化合物作为体外β-血红素形成的潜在抑制剂，并且测试了体内作为针对被对氯喹敏感的伯氏疟原虫ANKA菌株感染的小鼠的抗疟疾药物。化合物3a和4d延长了生存时间减少到17.00±1.26和20.20±1.95天，而感染的进展分别减少到4.02±0.45和3.05±0.09。评估了所有这些化合物对Jurkat E6.1和HL60这两种人类癌细胞系和新鲜人类淋巴细胞的细胞毒活性。四种化合物4a，n和5a，n对Jurkat E6.1和HL60细胞系显示出增强的细胞毒性。新鲜淋巴细胞不受影响。使用流式细胞仪，在24小时观察到凋亡细胞死亡。前述化合物增强两种肿瘤细胞系的凋亡，这是通过抑制自噬来降低细胞存活。
• BENZIMIDAZOLE DERIVATIVE
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0711768A1

  公开（公告）日：1996-05-15

  Disclosed are compounds represented by the following chemical formula (I) and pharmacologically acceptable salts thereof which are novel compounds useful as anticancer agents, antiviral agents or antimicrobial agents.

  所公开的是由以下化学式（I）代表的化合物及其药理学上可接受的盐类，它们是可用作抗癌剂、抗病毒剂或抗菌剂的新型化合物。
• US5852011A
  申请人：——

  公开号：US5852011A

  公开（公告）日：1998-12-22