2‑((2‑chlorobenzyl)thio)‑1H‑benzo[d]imidazole | 35838-26-7

• 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‑((2‑chlorobenzyl)thio)‑1H‑benzo[d]imidazole
• 英文别名: 2-(2-chloro-benzylsulfanyl)-1H-benzoimidazole；2-{[(2-chlorophenyl)methyl]sulfanyl}-1H-1,3-benzodiazole；2-[(2-chlorophenyl)methylsulfanyl]-1H-benzimidazole
• CAS: 35838-26-7
• 化学式: C₁₄H₁₁ClN₂S
• mdl: MFCD00442804
• 分子量: 274.774
• InChiKey: ZNOFJEVAANDKBD-UHFFFAOYSA-N

物化性质

• 沸点：
  476.1±47.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻苯二胺 在 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 2‑((2‑chlorobenzyl)thio)‑1H‑benzo[d]imidazole
  参考文献：
  名称：

  S-取代-2-巯基苯并咪唑类似物对脲酶抑制和DPPH自由基清除潜力的评价：合成、生物活性和分子对接研究

  摘要：

  通过将 2-巯基苯并咪唑与各种取代的苄基溴反应合成了几种S-取代的 2-巯基苯并咪唑衍生物 1-34 ，并借助各种光谱技术对其进行了表征。评估了所有合成化合物的脲酶抑制和 DPPH 自由基清除活性。与标准硫脲（IC 50  = 22.4 ± 0.29 µM）相比，化合物在 IC 50  = 16.8 ± 0.76–74.3 ± 0.72 µM范围内显示出显着至中等的脲酶抑制活性。值得一提的是，所有分子都表现出显着的 DPPH 自由基清除潜力，IC 50与标准丁基化羟基苯甲醚 BHA (IC 50  = 44.2 ± 0.45 µM)相比，值为 15.5 ± 0.58 至 89.3 ± 0.12 µM 。通过分析不同取代对脲酶抑制潜力的影响，提出了构效关系 (SAR)。进行了分子对接研究以简化配体（合成分子）与脲酶活性口袋的结合相互作用。此外，还评估 了最有效的化合物1-4、14、18、20

  DOI：

  10.1007/s13738-022-02653-1

文献信息

• Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles
  作者：Raoní Rambo、Etienne Waldow、Bruno Abaddi、Maiele Silveira、Adilio Dadda、Nathalia Sperotto、Cristiano Bizarro、Luiz Augusto Basso、Pablo Machado

  DOI：10.21577/0103-5053.20210040

  日期：——

  Using molecular simplification and molecular hybridization approaches, a series of 2-(benzylthio)-1H-benzo[d]imidazoles was synthesized and evaluated as in vitro inhibitors of Mycobacterium tuberculosis (M. tuberculosis) growth. Compounds 6p and 6z were considered the lead compounds from this series of molecules, with minimal inhibitory concentration (MIC) values of 6.9 and 3.8 μM against M. tuberculosis

  利用分子简化和分子杂化方法，合成了一系列2-(苄硫基)-1H-苯并[d]咪唑类化合物，并作为体外抑制结核分枝杆菌(M. tuberculosis)生长的试剂进行评估。该系列化合物中的6p和6z被认为是领先的化合物，对M. tuberculosis H37Rv的最小抑制浓度（MIC）分别为6.9和3.8μM。此外，这些领先的化合物对多药耐药菌株也具有活性，并且对Vero和HepG2细胞没有明显毒性，这是通过3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴化物（MTT）和中性红试验得出的。最后，这些化合物具有良好的水溶性和高的血浆稳定性。这些数据表明，这一类分子可能为未来开发新的抗结核病药物候选物提供了可能性。
• Synthesis and preliminary evaluation of benzimidazole derivatives as antimicrobial agents
  作者：Věra Klimešová、Jan Kočı́、Milan Pour、Jiřı́ Stachel、Karel Waisser、Jarmila Kaustová

  DOI：10.1016/s0223-5234(02)01342-9

  日期：2002.5

  A series of 2-alkylsulphanylbenzimidazoles was synthesised and the compounds were evaluated for their in vitro antimicrobial activity. The structures of the compounds were confirmed by H-1-NMR and IR data, and their purity by elemental analysis. Antimycobacterial activities against Mycobacterium tuberculosis and non-tuberculous mycobacteria as well as antifungal activities against Candida albicans, Candida tropicalis, Candida krusei, Candida glabrata, Trichosporon beigelii, Trichophyton mentagrophytes and Aspergillus fumigatus were expressed as the corresponding MIC values. The substances exhibited appreciable antimycobacterial activity, in particular, against non-tuberculous mycobacteria. The activity of the most active compound in the set, 3,5-dinitro derivative 4t, exceeded that of the standard isoniazide against M. kansasii and M. avium. The antifungal activities of the compounds were relatively low. A weak antifungal effect was observed against the dermatophyte Trichophyton mentagrophytes. None of the compounds showed significant inhibitory activity against yeasts. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• DBU-Promoted Deaminative Thiolation of 1<i>H</i>-Benzo[<i>d</i>]imidazol-2-amines and Benzo[<i>d</i>]oxazol-2-amines
  作者：Lvyin Zheng、Weijie Mei、Xiaoying Zou、Yumei Zhong、Yingying Wu、Lei Deng、Yihan Wang、Beining Yang、Wei Guo

  DOI：10.1021/acs.joc.2c02297

  日期：2023.1.6

  deaminative thiolation reaction of 1H-benzo[d]imidazol-2-amines and benzo[d]oxazol-2-amines has been developed at room temperature conditions in a one-pot protocol. This practical three-component strategy represents a novel and environmentally friendly reaction pathway toward the straightforward synthesis of various 2-thio-1H-benzo[d]imidazoles and 2-thiobenzo[d]oxazoles using carbon disulfide as a
• REL INHIBITORS AND METHODS OF USE THEREOF
  申请人：Chen Youhai H.

  公开号：US20110118325A1

  公开（公告）日：2011-05-19

  This invention provides REL inhibitors which interfere with the DNA binding capacity of a REL protein. Additionally this invention provides methods of treating, abrogating, or preventing diseases which respond with a positive clinical score to a REL inhibitor. Methods of identifying REL inhibitor based on a REL protein three dimensional model are described.
• CN114989096
  申请人：——

  公开号：——

  公开（公告）日：——