2-((1H-benzo[d]imidazol-2-yl)thio)-1-(4-fluorophenyl)ethan-1-one | 63529-32-8

• 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-fluorophenyl)ethan-1-one
• 英文别名: 2-[(1H-benzo[d]imidazol-2-yl)thio]-1-(4-fluorophenyl)ethan-1-one；2-(1H-benzo[d]imidazol-2-ylthio)-1-(4-fluorophenyl)ethanone；2-(1H-Benzimidazol-2-ylsulfanyl)-1-(4-fluorophenyl)ethanone
• CAS: 63529-32-8
• 化学式: C₁₅H₁₁FN₂OS
• 分子量: 286.33
• InChiKey: RUYDNBJGEQMPJK-UHFFFAOYSA-N

物化性质

• 沸点：
  504.9±56.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  4

反应信息

• 作为反应物：
  描述：

  2-((1H-benzo[d]imidazol-2-yl)thio)-1-(4-fluorophenyl)ethan-1-one 在 Oxone 、 sodium tetrahydroborate 、 氢溴酸 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 叔丁醇 为溶剂， 生成 2-[(E)-2-(4-fluorophenyl)ethenyl]sulfonyl-1H-benzimidazole
  参考文献：
  名称：

  New styryl sulfones as anticancer agents

  摘要：

  New styryl sulfone compounds have been synthesized and evaluated for their anti-proliferative activity. Among the compounds synthesized, one compound (7k) has shown 51% tumor growth inhibition in mice implanted with HT-29 human carcinoma at 400 mg kg(-1) orally. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00144-2
• 作为产物：
  描述：

  2-((2-(4-fluorophenyl)-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-fluorophenyl)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

• 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。
• 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。
• 2-((Benzimidazol-2-yl)thio)-1-arylethan-1-ones: Synthesis, crystal study and cancer stem cells CD133 targeting potential
  作者：Hatem A. Abdel-Aziz、Hazem A. Ghabbour、Wagdy M. Eldehna、Sara T.A. Al-Rashood、Khalid A. Al-Rashood、Hoong-Kun Fun、Mays Al-Tahhan、Abdullah Al-Dhfyan

  DOI：10.1016/j.ejmech.2015.09.023

  日期：2015.11

  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.
• New styryl sulfones as anticancer agents
  作者：Manohar Sharma Vedula、Aravind Babu Pulipaka、Chandrasekhar Venna、Vamsee Krishna Chintakunta、Sreenu Jennepalli、Venkata Adiseshu Kattuboina、Ravi Krishna Vallakati、Vishnu Basetti、Venkateswarlu Akella、Sriram Rajgopal、Ajaya Kumar Reka、Sravan Kumar Teepireddy、Prem Kumar Mamnoor、Ramanujam Rajagopalan、Gopalakrishnan Bulusu、Akash Khandelwal、Vijay V Upreti、Srinivas Rao Mamidi

  DOI：10.1016/s0223-5234(03)00144-2

  日期：2003.9

  New styryl sulfone compounds have been synthesized and evaluated for their anti-proliferative activity. Among the compounds synthesized, one compound (7k) has shown 51% tumor growth inhibition in mice implanted with HT-29 human carcinoma at 400 mg kg(-1) orally. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.