2-((1H-benzo[d]imidazol-2-yl)thio)-1-(4-methoxyphenyl)ethan-1-one | 22794-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((1H-benzo[d]imidazol-2-yl)thio)-1-(4-methoxyphenyl)ethan-1-one
• 英文别名: 2-(1H-benzimidazol-2-ylsulfanyl)-1-(4-methoxyphenyl)ethanone
• CAS: 22794-86-1
• 化学式: C₁₆H₁₄N₂O₂S
• 分子量: 298.365
• InChiKey: FPGBMTGFXJAICB-UHFFFAOYSA-N

物化性质

• 沸点：
  544.7±56.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((1H-benzo[d]imidazol-2-yl)thio)-1-(4-methoxyphenyl)ethan-1-one 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-methoxyphenyl)-2-oxoethyl)thio)-1H-benzo[d]imidazol-3-ium sulfate salt 以 水 为溶剂， 反应 2.0h， 生成 2-((1H-benzo[d]imidazol-2-yl)thio)-1-(4-methoxyphenyl)ethan-1-one
  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

• 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, Crystal Study, and Anti-Proliferative Activity of Some 2-Benzimidazolylthioacetophenones towards Triple-Negative Breast Cancer MDA-MB-468 Cells as Apoptosis-Inducing Agents
  作者：Hatem Abdel-Aziz、Wagdy Eldehna、Hazem Ghabbour、Ghada Al-Ansary、Areej Assaf、Abdullah Al-Dhfyan

  DOI：10.3390/ijms17081221

  日期：——

  On account of its poor prognosis and deficiency of therapeutic stratifications, triple negative breast cancer continues to form the causative platform of an incommensurate number of breast cancer deaths. Aiming at the development of potent anticancer agents as a continuum of our previous efforts, a novel series of 2-((benzimidazol-2-yl)thio)-1-arylethan-1-ones 5a–w was synthesized and evaluated for its anti-proliferative activity towards triple negative breast cancer (TNBC) MDA-MB-468 cells. Compound 5k was the most active analog against MDA-MB-468 (IC50 = 19.90 ± 1.37 µM), with 2.1-fold increased activity compared to 5-fluorouracil (IC50 = 41.26 ± 3.77 µM). Compound 5k was able to induce apoptosis in MDA-MB-468, as evidenced by the marked boosting in the percentage of florecsein isothiocyanate annexin V (Annexin V–FITC)-positive apoptotic cells (upper right (UR) + lower right (LR)) by 2.8-fold in comparison to control accompanied by significant increase in the proportion of cells at pre-G1 (the first gap phase) by 8.13-fold in the cell-cycle analysis. Moreover, a quantitative structure activity relationship (QSAR) model was established to investigate the structural requirements orchestrating the anti-proliferative activity. Finally, we established a theoretical kinetic study.

  由于其预后不良和治疗分层的不足，三阴性乳腺癌继续成为导致乳腺癌死亡人数不相称的原因平台。作为我们之前努力的连续体，旨在开发有效的抗癌药物，合成了一系列新型 2-((benzimidazol-2-yl)thio)-1-aryllethan-1-ones 5a–w 并评估了其抗癌效果。 -对三阴性乳腺癌（TNBC）MDA-MB-468细胞的增殖活性。化合物 5k 是 MDA-MB-468 活性最强的类似物 (IC50 = 19.90 ± 1.37 µM)，与 5-氟尿嘧啶相比，活性增加了 2.1 倍 (IC50 = 41.26 ± 3.77 µM)。化合物 5k 能够诱导 MDA-MB-468 细胞凋亡，异硫氰酸荧光素膜联蛋白 V (Annexin V–FITC) 阳性凋亡细胞的百分比显着增加（右上 (UR) + 右下 (LR)） ）与对照相比增加了 2.8 倍，同时在细胞周期分析中，G1 前（第一个间隙期）的细胞比例显着增加了 8.13 倍。此外，还建立了定量结构活性关系（QSAR）模型来研究协调抗增殖活性的结构要求。最后，我们建立了理论动力学研究。
• A convenient one-pot synthesis of 2-benzimidazolyl-thioacetophenones and thiazolo[3,2-a]benzimidazoles
  作者：Abd El-Wareth A.O. Sarhan、Hasan A.H. El-Sherief、Abdalla M. Mahmoud

  DOI：10.1016/0040-4020(96)00569-8

  日期：1996.7

  etophenones 3a-d. Which on cyclization yield thiazolo[3,2-a]-benzimidazoles 4a-d. Acetylation of 3a,d gave the N-acetyl derivatives 5a,d. Cyclization of 3a-d or 5d in acetic anhydride or acetic anhydride / pyridine mixture afforded 6a-d. While reaction of 1 with aliphatic or alicyclic ketones gave directly 2,3-disubstituted thiazolo[3,2-a]benzimidazoles 7a-f and 8a-d respectively.

  2-巯基苯并咪唑（1）与芳族酮2a-d在酸化的乙酸中反应，得到2-苯并咪唑基硫代乙酰基苯乙酮3a-d。在环化反应中产生噻唑并[3，2-a]-苯并咪唑4a-d。3a，d的乙酰化得到N-乙酰基衍生物5a，d。3a-d或5d在乙酸酐或乙酸酐/吡啶混合物中的环化得到6a-d。当1与脂族或脂环族酮反应时，分别直接直接得到2，3-二取代的噻唑并[3，2-a]苯并咪唑7a-f和8a-d。
• A facile one pot synthesis of thiazolo[3,2-<i>a</i>]benzimidazole and pyran fused polyheterocyclic scaffolds
  作者：Arumugam Mariappan、Kandasamy Rajaguru、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1039/c9ob00300b

  日期：——

  An efficient synthesis of dihydro-4H-benzo[4,5]imidazo[2,1-b]pyrano[2,3-d]thiazole by a multicomponent route starting from 2-((1H-benzo[d]imidazol-2-yl)thio)-1-phenylethan-1-one, an aromatic aldehyde and malononitrile is described. This protocol features a metal free approach with good substrate scope and decent yield. The heterocyclic skeleton obtained in this study may have interesting biological

  从2-（（1 H-苯并[ d ]咪唑）开始的多组分路线有效合成二氢-4 H-苯并[4,5]咪唑并[2,1- b ]吡喃并[2,3- d ]噻唑描述了-2-基）硫基）-1-苯基乙-1-酮，芳族醛和丙二腈。该协议采用无金属方法，具有良好的基板范围和良好的成品率。在这项研究中获得的杂环骨架可能具有有趣的生物学特性。
• Design, Synthesis, In Vitro Biological Evaluation and In Silico Molecular Docking Study of Benzimidazole-Based Oxazole Analogues: A Promising Acetylcholinesterase and Butyrylcholinesterase Inhibitors
  作者：Rafaqat Hussain、Fazal Rahim、Hayat Ullah、Shoaib Khan、Maliha Sarfraz、Rashid Iqbal、Faiza Suleman、Mohammad Khalid Al-Sadoon

  DOI：10.3390/molecules28207015

  日期：——

  out for the synthesis of benzimidazole-oxazole hybrid derivatives as efficient Alzheimer’s inhibitors and as a springboard for investigating novel anti-chemical Alzheimer’s prototypes. The inhibition profiles of each synthesised analogue against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes were assessed. All the synthesized benzimidazole-based oxazole analogues displayed a

  阿尔茨海默病（AD）是一种严重影响老年人的退行性神经系统疾病，临床上表现为认知和记忆力下降。由于多种因素，包括患者人数随着时间的推移而增加、患者生活质量显着下降以及治疗和护理费用高。目前的工作是合成苯并咪唑-恶唑杂化衍生物作为有效的阿尔茨海默病抑制剂，并作为研究新型抗化学阿尔茨海默病原型的跳板。评估了每种合成类似物对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）的抑制谱。与参考药物多奈哌齐相比，所有合成的基于苯并咪唑的恶唑类似物均显示出针对目标 AChE 和 BuChE 酶的多种抑制潜力（IC50 分别为 2.16 ± 0.12 M 和 4.50 ± 0.11 µM）。发现最活跃的 AChE 和 BuChE 类似物是类似物 9 和 14，IC50 值分别为 0.10 ± 0.050 和 0.20 ± 0.050 µM（针对 AChE）以及 0.20 ± 0.050 和 0.30 ± 0