2-((4-fluorobenzyl)thio)-1H-benzo[d]imidazole

• 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-((4-fluorobenzyl)thio)-1H-benzo[d]imidazole
• 英文别名: 2-[(4-fluorophenyl)methylsulfanyl]-1H-benzimidazole
• 化学式: C₁₄H₁₁FN₂S
• 分子量: 258.319
• InChiKey: OMXRCMRPDVPIDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-N,N-二丙基乙酰胺 、 2-((4-fluorobenzyl)thio)-1H-benzo[d]imidazole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以80%的产率得到2-(2-((4-fluorobenzyl)thio)-1H-benzo[d]imidazol-1-yl)-N,N-dipropylacetamide
  参考文献：
  名称：

  Discovery of benzimidazole derivatives as modulators of mitochondrial function: A potential treatment for Alzheimer's disease

  摘要：

  In this study, we designed a library of compounds based on the structures of well-known ligands of the 18 kDa translocator protein (TSPO), one of the putative components of the mPTP. We performed diverse mitochondrial functional assays to assess their ability to restore cells from A beta-induced toxicity in vitro and in vivo. Among tested compounds, compound 25 effectively improved cognitive function in animal models of AD. Given the excellent in vitro and in vivo activity and a favorable pharmacokinetic profile of compound 25, we believe that it can serve as a promising lead compound for a potential treatment option for AD. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.11.017
• 作为产物：
  描述：

  1H-苯并咪唑-2-硫醇 、 4-氟溴苄 在 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 以88%的产率得到2-((4-fluorobenzyl)thio)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Discovery of benzimidazole derivatives as modulators of mitochondrial function: A potential treatment for Alzheimer's disease

  摘要：

  In this study, we designed a library of compounds based on the structures of well-known ligands of the 18 kDa translocator protein (TSPO), one of the putative components of the mPTP. We performed diverse mitochondrial functional assays to assess their ability to restore cells from A beta-induced toxicity in vitro and in vivo. Among tested compounds, compound 25 effectively improved cognitive function in animal models of AD. Given the excellent in vitro and in vivo activity and a favorable pharmacokinetic profile of compound 25, we believe that it can serve as a promising lead compound for a potential treatment option for AD. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.11.017

文献信息

• Three‐Component Synthesis of 2‐Substituted Thiobenzoazoles Using Tetramethyl Thiuram Monosulfide (TMTM) as Thiocarbonyl Surrogate
  作者：Xi Wang、Chun‐Yan Wu、Yue‐Sheng Li、Zhi‐Bing Dong

  DOI：10.1002/ejoc.202001214

  日期：2020.11.22

  A metal‐free synthesis of 2‐benzyl/allyl‐substituted thiobenzoazoles was developed starting from tetramethyl thiuram monosulfide (TMTM) which served as thiocarbonyl surrogate. By using 2‐aminophenols (or 2‐aminothiophenols, or 1,2‐phenylenediamines) and TMTM as starting materials, 2‐mercaptobenzoazoles could be synthesized efficiently, and the subsequent C–S bond formation with allyl/benzyl halides

  从用作硫代羰基替代物的四甲基秋兰姆单硫化物（TMTM）出发，开发了2-苄基/烯丙基取代的硫代苯并恶唑的无金属合成方法。通过使用2-氨基苯酚（或2-氨基硫酚或1,2-苯二胺）和TMTM作为起始原料，可以高效合成2-巯基苯并恶唑，随后与烯丙基/苄基卤化物的CS键形成最终产物（ 2-烯丙基/苄基取代的硫代苯并唑），具有良好或优异的收率。
• 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
• CN114989096
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery of benzimidazole derivatives as modulators of mitochondrial function: A potential treatment for Alzheimer's disease
  作者：TaeHun Kim、Ha Yun Yang、Beoung Gun Park、Seo Yun Jung、Jong-Hyun Park、Ki Duk Park、Sun-Joon Min、Jinsung Tae、Hyejin Yang、Suengmok Cho、Sung Jin Cho、Hyundong Song、Inhee Mook-Jung、Jiyoun Lee、Ae Nim Pae

  DOI：10.1016/j.ejmech.2016.11.017

  日期：2017.1

  In this study, we designed a library of compounds based on the structures of well-known ligands of the 18 kDa translocator protein (TSPO), one of the putative components of the mPTP. We performed diverse mitochondrial functional assays to assess their ability to restore cells from A beta-induced toxicity in vitro and in vivo. Among tested compounds, compound 25 effectively improved cognitive function in animal models of AD. Given the excellent in vitro and in vivo activity and a favorable pharmacokinetic profile of compound 25, we believe that it can serve as a promising lead compound for a potential treatment option for AD. (C) 2016 Elsevier Masson SAS. All rights reserved.