2-(4-Brom-phenacyl-mercapto)-benzimidazol | 21547-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-Brom-phenacyl-mercapto)-benzimidazol
• 英文别名: 2-(1H-Benzimidazol-2-ylsulfanyl)-1-(4-bromophenyl)ethanone
• CAS: 21547-82-0
• 化学式: C₁₅H₁₁BrN₂OS
• mdl: MFCD00429016
• 分子量: 347.235
• InChiKey: MZWHCEWSSISORO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Brom-phenacyl-mercapto)-benzimidazol 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, in vitro alpha-glucosidase inhibitory potential of benzimidazole bearing bis-Schiff bases and their molecular docking study

  摘要：

  Voglibose and acarbose are distinguished alpha-glucosidase inhibitors used for controlling of diabetes mellitus. Unfortunately, these distinguished and clinically used inhibitors have also numerous side effects. Subsequently, there is still needed to develop safer therapy. Despite of a broad spectrum of biological importance of benzimidazole, it is occasionally evaluated for alpha-glucosidase activity. Current study deals with the synthesis and biological screening of benzimidazole bearing bis-Schiff bases (1-19) for their alpha-glucosidase inhibitory activity. All analogues exhibited excellent to good inhibitory potential (IC50 = 2.20 +/- 0.1to 88.60 +/- 1.70 mu M) when compared with standard drug acarbose (IC50 = 38.45 +/- 0.80 mu M). A structure activity relationship has been established on the basis of electronic effects and position of different substituents present on phenyl ring. In order to rationalize the binding interactions of most active analogues with the active site of alpha-glucosidase enzyme, molecular docking study was conducted.

  DOI：

  10.1016/j.bioorg.2019.103394
• 作为产物：
  描述：

  2-((2-(4-bromophenyl)-2-oxoethyl)thio)-1H-benzo[d]imidazol-3-ium sulfate salt 以 水 为溶剂， 反应 2.0h， 生成 2-(4-Brom-phenacyl-mercapto)-benzimidazol
  参考文献：
  名称：

  2-((Benzimidazol-2-yl)thio)-1-arylethan-1-ones: Synthesis, crystal study and cancer stem cells CD133 targeting potential

  摘要：

  In order to develop a potent anti-tumor agent that can target both cancer stem cells and the bulk of tumor cells, a series of 2-((benzimidazol-2-yl)thio)-1-arylethan-1-ones 5a-o was synthesized. All compounds were evaluated for their anti-proliferative activity towards colon HT-29 cancer cell line. In addition, their inhibitory effect against cell surface expression of CD133, a potent cancer stem cells (CSCs) marker, in the same cells was evaluated by flow cytometry at 10 mu M. Compound 51 emerged as the most active anti-proliferative analog against HT-29 (IC50 = 18.83 +/- 1.37 mu M), that almost equipotent as 5-fluorouracil (IC50 = 15.83 +/- 1.63 mu M) with 50.11 +/- 4.05% inhibition effect on CD133 expression, suggested dual targeted effect. Also, compounds 5h, 5j, 5k and 5m-o inhibited the expression of CD133 with more than 50%. The SAR study pointed out the significance of substitution of the pendent phenyl group with lipophilic electron-donating groups or replacing it by 2-thienyl or 2-furyl groups. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.023

文献信息

• Zinc Oxide Catalyzed Solvent-Free Mechanochemical Route for C-S Bond Construction: A Sustainable Process
  作者：P. Md. Khaja Mohinuddin、N. C. Gangi Reddy

  DOI：10.1002/ejoc.201601425

  日期：2017.2.24

  Zinc oxide-catalyzed solvent-free mechanochemical route has been developed for the rapid construction of C-S bond using a variety of thiols and phenacyl/benzyl/alkyl bromides via a nucleophilic substitution (SN2 mechanism). Notable advantages of this method include broad substrate scope, cleaner reaction profile, safe, scalable, high yields at ambient conditions and reuse of catalyst. Further, the

  已经开发了氧化锌催化的无溶剂机械化学路线，通过亲核取代（SN2 机制）使用各种硫醇和苯甲酰/苄基/烷基溴化物快速构建 CS 键。这种方法的显着优点包括广泛的底物范围、更清洁的反应曲线、安全、可扩展、环境条件下的高产率和催化剂的重复使用。此外，制备的合成前体是各种生物活性分子合成中的重要组成部分。
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2004011410A1

  公开（公告）日：2004-02-05

  Compounds of formula (I):wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  式(I)的化合物：其中变量基团如定义内；用于抑制11βHSD1。
• Synthesis of benzimidazole derivatives as potent inhibitors for α-amylase and their molecular docking study in management of type-II diabetes
  作者：Shafqat Hussain、Muhammad Taha、Fazal Rahim、Shawkat Hayat、Khalid Zaman、Naveed Iqbal、Manikandan Selvaraj、Muhammad Sajid、Masroor Ahmad Bangesh、Fahad Khan、Khalid Mohammed Khan、Nizam Uddin、Syed Adnan Ali Shah、Muhammad Ali

  DOI：10.1016/j.molstruc.2021.130029

  日期：2021.5

  standard drug acarbose. While others derivatives of the series showed good inhibitory potentials. All the synthesized compounds were characterized by HREI-MS, 1H and 13C-NMR spectroscopy. Structure activity relationship (SAR) has been established for all newly synthesized analogs. Binding interactions between ligands and active residues of the enzyme were confirmed through molecular docking study.

  在寻找有效的α-淀粉酶抑制剂的过程中，我们合成了十七种带有磺酰胺的2-巯基苯并咪唑衍生物（1-17），并评估了它们的α-淀粉酶抑制潜力。所有合成的化合物显示的可变程度α-淀粉酶活性的具有IC 50值0.90±0.30 11.20 0.05到±测距μ当与标准药物阿卡波糖具有IC相比中号50值1.70±0.10 μ M.化合物1，2，11 ，12和14的IC 50值为1.40±0.10、1.30±0.05、0.90±0.05、1.60±0.05和1.60±0.10 µM分别被发现比标准药物阿卡波糖好很多倍。而该系列的其他衍生物则显示出良好的抑制潜力。所有合成的化合物均通过HREI-MS，1 H和13 C-NMR光谱进行表征。已经为所有新合成的类似物建立了结构活性关系（SAR）。通过分子对接研究证实了配体与酶的活性残基之间的结合相互作用。
• Synthesis of difluorinated β-ketosulfones and novel gem-difluoromethylsulfone-containing heterocycles as fluorinated building blocks
  作者：Hossein Loghmani-Khouzani、Dariush Hajiheidari

  DOI：10.1016/j.jfluchem.2009.12.022

  日期：2010.5

  A series of new heterocyclic β-ketosulfides was prepared by the reaction of the corresponding heterocyclic thiols with α-bromoacetophenone and its derivatives. Oxidation of the products using m-CPBA gave the corresponding heterocyclic β-ketosulfones, which, on treatment with Selectfluor™ under anhydrous condition underwent electrophilic fluorination resulting in new heterocycles with difluoromethylene

  通过相应的杂环硫醇与α-溴苯乙酮及其衍生物的反应，制备了一系列新的杂环β-酮硫醚。使用产品的氧化米-CPBA得到相应的杂环β-酮砜，其中，无水条件下使用的Selectfluor™治疗经历导致与相邻的硫原子和羰基二氟亚甲基部分的新的杂环电氟化。以不同的杂环部分作为模型化合物，对五种类型的所得产物进行碱基诱导的裂解，得到与相应杂环连接的二氟甲基砜。它们可以被认为是用于进一步阐述的有趣的氟化构建基块。
• A New Aspect of the Pfitzinger Reaction: Microwave-assisted Synthesis of the New Heterocyclic Ring System 6-Arylbenzo[4,5]imidazolo[2,1-b]quino[4,3-e]-1,3-thiazin-14-one
  作者：Hatem A. Abdel-Aziz、Sobhi M. Gomha

  DOI：10.1515/znb-2009-0709

  日期：2009.7.1

  We report herein on the utility of the Pfitzinger reaction in a facile two-step synthesis of the new heterocyclic ring system 6-arylbenzo[4,5]imidazolo[2,1-b]quino[4,3-e]-1,3-thiazin-14-one using microwave irradiation (MWI) and/or conventional heating. Microwave irradiation was used for a rapid and efficient synthesis of quinoline-4-carboxylic acids 6a - d from the reaction of isatin with 2-(1Hbenzimidazol- 2-ylthio)-1-arylethanones 3a - d. Cyclization of cinchoninic acids 6a - d afforded the fused title compounds 7a - d.

  我们在此报告了Pfitzinger反应在新的杂环环系统6-芳基苯并[4,5]咪唑并[2,1-b]喹诺[4,3-e]-1,3-噻唑-14-酮的简便两步合成中的实用性，使用微波辐射（MWI）和/或常规加热。微波辐射用于通过异喹啉与2-(1H苯并咪唑-2-基硫基)-1-芳基乙酮酮的反应快速高效地合成喹啉-4-羧酸6a-d。6a-d的辛克酸环化形成了融合的标题化合物7a-d。