1-(1H-benzoimidazol-2-yl)-3-(2-hydroxy-phenyl)-propenone | 62306-36-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(1H-benzoimidazol-2-yl)-3-(2-hydroxy-phenyl)-propenone
• 英文别名: 1-(1H-Benzimidazol-2-yl)-3-(2-hydroxyphenyl)prop-2-en-1-one；1-(1H-benzimidazol-2-yl)-3-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 62306-36-9
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: AWMBALQXJFUUMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1H-benzoimidazol-2-yl)-3-(2-hydroxy-phenyl)-propenone 在 ammonium acetate 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 16.0h， 生成 6-(1H-benzo[d]imidazol-2-yl)-2-(benzylideneamino)-4-(2-hydroxyphenyl)nicotinonitrile
  参考文献：
  名称：

  Synthesis, antimicrobial and cytotoxic activity of 2-azetidinone derivatives of pyridyl benzimidazoles

  摘要：

  In the present study, a series of novel 6-(1H-benzo[d]imidazol-2-yl)-2-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-4-(aryl)nicotinonitriles 6a-o were efficiently synthesized and evaluated for their in vitro antibacterial activity against Gram-positive (Staphylococcus aureus and Streptococcus pyogenes), Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria and fungal (Candida albicans, Aspergillus niger and Aspergillus clavatus) strains. The results of antimicrobial study revealed that compounds 6b, 6c, 6d, 6h and 6i exhibited substantial antibacterial activity while compounds 6c and 6h emerged as the most potent antifungal agents compared to the standard drugs chloramphenicol and ketoconazole, respectively. From the standpoint of SAR studies, it was observed that the presence of electron-withdrawing groups remarkably enhances the antibacterial activity of newly synthesized compounds. Further, the results of preliminary MTT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 6b, 6c, 6d, 6h and 6i is accompanied by low level of cytotoxic concentrations. All the newly synthesized analogues were characterized by IR, H-1 NMR, C-13 NMR and mass spectral data.

  DOI：

  10.1007/s00044-013-0775-1
• 作为产物：
  描述：

  2-(1-羟乙基)苯并咪唑 在 potassium dichromate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 1-(1H-benzoimidazol-2-yl)-3-(2-hydroxy-phenyl)-propenone
  参考文献：
  名称：

  Design and structure-activity relationships anticandidosic of diazaheteroaryl functionalized by Michaël acceptors

  摘要：

  念珠菌病的管理，曾经有效，但随着各种念珠菌对经典 antifungals 抗药性的增加，变得越来越困难。在这种背景下，我们在之前的研究中报告了新的二氮杂杂环芳烃衍生物的药物化学开发，这些衍生物与 Michael 受体（如芳基丙烯酮、芳基丙烯腈和芳基氰丙烯酮）功能化。这些具有苯并咪唑基-芳基丙烯酮、苯并咪唑基-芳基丙烯腈或苯并咪唑基-芳基氰丙烯酮及咪唑并吡啶基-芳基丙烯酮结构的二氮杂杂环芳烃衍生物通过化学合成获得，然后通过常规的光谱方法（NMR 和 MS）进行表征。这些衍生物的抗念珠菌活性以最小抑制浓度（MIQ）在体外检测，使用了生物自走技术，针对临床株的白色念珠菌进行测试。结果显示，经 Michael 受体功能化的二氮杂杂环芳烃具有显著的活性，IMQ 范围为 10 到 0.16 微克。此外，不同衍生物的抗念珠菌性能与 Michael 受体的性质及在苯环上的结构变化相关。本论文是我们团队十年研究的总结，将涉及药物化学设计、化学合成及整体系列结构-抗念珠菌活性研究，以提出能够发展为抗念珠菌药物候选物的化合物。

  DOI：

  10.21608/ejchem.2021.87021.4207

文献信息

• Synthesis and antimicrobial activity of some heterocyclic compounds bearing benzimidazole and pyrazoline motifs
  作者：N. C. Desai、Darshan Pandya、Darshita Vaja

  DOI：10.1007/s00044-017-2040-5

  日期：2018.1

  antimicrobial activity against gram positive (S. aureus and S. pyogenes), gram negative bacteria (E. coli and P. aeruginosa), and strains of fungi (C. albicans, A. niger, and A. clavatus). Compounds were characterized by spectroscopic techniques such as 1H NMR, 13C NMR, IR, and mass spectroscopy. The newly synthesized compounds 5b, 5i and 5j, 5k showed significant antimicrobial activity against tested

  摘要一系列1-（3-（1 H-苯并咪唑-2-基）-5-芳基-4-5二氢-1 H-吡唑-1-基）-2-（萘-1-基氧基）乙酮（5a –升）被合成并评价了它们的抗微生物活性对革兰氏阳性（金黄色葡萄球菌和化脓性链球菌），革兰氏阴性细菌（大肠杆菌和绿脓杆菌），和真菌的菌株（白色念珠菌，黑曲霉，和甲。clavatus）。通过光谱技术，例如1 H NMR，13 C NMR，IR和质谱对化合物进行表征。新合成的化合物5b，5i和5j，5k显示出对测试微生物的显着抗微生物活性。 图形概要
• Synthesis and characterization of novel benzimidazole bearing pyrazoline derivatives as potential antimicrobial agents
  作者：N. C. Desai、D. D. Pandya、G. M. Kotadiya、Priyanka Desai

  DOI：10.1007/s00044-013-0756-4

  日期：2014.3

  A new series of compounds N-(4-(2-(3-(1H-benzo[d]imidazol-2-yl)-5-(aryl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethoxy)phenyl)acetamides (5a–u) were synthesized and structures of these compounds were elucidated by spectral (IR, 1H NMR, 13C NMR, and mass spectra) analysis. Antimicrobial activity was measured against Escherichia coli (MTCC 443), Pseudomonas aeruginosa (MTCC 1688), Staphylococcus aureus (MTCC

  一系列新的化合物N-（4-（2-（3-（1 H-苯并[ d ]咪唑-2-基] -5-（芳基）-4,5-二氢-1 H-吡唑-1-合成了yl）-2-氧代乙氧基）苯基）乙酰胺（5a - u），并通过光谱分析（IR，1 H NMR，13 C NMR和质谱）阐明了这些化合物的结构。测量了对大肠杆菌（MTCC 443），铜绿假单胞菌（MTCC 1688），金黄色葡萄球菌（MTCC 96），化脓性链球菌（MTCC 442），白色念珠菌（MTCC 227），黑曲霉（Aspergillus niger）的抗菌活性（MTCC 282）和曲霉曲霉（MTCC 1323）的连续肉汤稀释法。抗菌活性的评估表明，与标准药物相比，化合物5f，5i，5q和5t是最有效的抗菌剂，而化合物5e，5g，5h，5j，5p，5r和5u是最有效的抗菌剂，因此有望成为新的铅分子。
• Activation of p53 signaling and regression of breast and prostate carcinoma cells by spirooxindole-benzimidazole small molecules
  作者：Assem Barakat、Saeed Alshahrani、Abdullah Mohammed Al-Majid、Abdullah Saleh Alamary、Matti Haukka、Marwa M. Abu-Serie、Alexander Dömling、Luis R. Domingo、Yaseen A. M. M. Elshaier

  DOI：10.3389/fphar.2024.1358089

  日期：——

  quantified using IC50 values. This study highlights activation of the p53 pathway by compounds 6a and 6d, leading to upregulation of p53 expression and downregulation of cyclin D and NF-κB in treated cells. Additionally, we explored the binding affinity of spirooxindole analogs, particularly compound 6d, to MDM2, a protein involved in regulation of p53. The binding mode and position of compound 6d were

  本研究讨论了新的螺吲哚-苯并咪唑化合物库的合成和用途，作为信号转导器的抑制剂和 p53 的激活剂，p53 是一种参与调节细胞生长和癌症预防的蛋白质。该文本包括分子电子密度理论框架内偶氮甲碱叶立德 7a 和乙烯 3a 之间的 [3 + 2] 环加成 (32CA) 反应的科学细节。 32CA反应的机理是通过两阶段一步过程，重点是高度异步的过渡状态结构。评估了合成化合物，特别是6a和6d的抗癌特性。使用 IC 定量这些化合物对肿瘤细胞（MDA-MB 231 和 PC-3）生长的抑制作用50价值观。这项研究强调了化合物 6a 和 6d 激活 p53 通路，导致处理细胞中 p53 表达上调以及细胞周期蛋白 D 和 NF-κB 下调。此外，我们还探讨了螺吲哚类似物（特别是化合物 6d）与 MDM2（一种参与 p53 调节的蛋白质）的结合亲和力。将化合物 6d 的结合模式和位置​​与共结晶标准配体的结合
• Synthesis, antimicrobial, and cytotoxic activities of novel benzimidazole derivatives bearing cyanopyridine and 4-thiazolidinone motifs
  作者：N. C. Desai、D. D. Pandya、K. A. Bhatt、G. M. Kotadiya、Priyanka Desai

  DOI：10.1007/s00044-014-0971-7

  日期：2014.8

  A series of 6-(1H-benzo[d]imidazol-2-yl)-2-(2-(3-nitrophenyl)-4-oxothiazolidin-yl)-4-(aryl)nicotinonitriles 5a-l were synthesized and characterized by IR, H-1 NMR, C-13 NMR, and mass spectrometry techniques. These novel compounds 5a-l were screened for their in vitro antimicrobial activity against different bacterial and fungal strains and in vitro cytotoxicity study (HeLa cell line) using MTT colorimetric assay. The results demonstrated that compounds 5c, 5e, and 5i-k exhibited excellent antibacterial activity, while compounds 5d, 5i, and 5k were found to be the most potent antifungal agents. From the standpoint of SAR studies, it was observed that the presence of electron donating groups remarkably enhanced the antimicrobial activity of newly synthesized compounds. Further, the results of preliminary MTT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 5c-e and 5i-k was accompanied by low cytotoxicity.
• Synthesis, antimicrobial and cytotoxic activity of 2-azetidinone derivatives of pyridyl benzimidazoles
  作者：N. C. Desai、D. D. Pandya、G. M. Kotadiya、Priyanka Desai

  DOI：10.1007/s00044-013-0775-1

  日期：2014.4

  In the present study, a series of novel 6-(1H-benzo[d]imidazol-2-yl)-2-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-4-(aryl)nicotinonitriles 6a-o were efficiently synthesized and evaluated for their in vitro antibacterial activity against Gram-positive (Staphylococcus aureus and Streptococcus pyogenes), Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria and fungal (Candida albicans, Aspergillus niger and Aspergillus clavatus) strains. The results of antimicrobial study revealed that compounds 6b, 6c, 6d, 6h and 6i exhibited substantial antibacterial activity while compounds 6c and 6h emerged as the most potent antifungal agents compared to the standard drugs chloramphenicol and ketoconazole, respectively. From the standpoint of SAR studies, it was observed that the presence of electron-withdrawing groups remarkably enhances the antibacterial activity of newly synthesized compounds. Further, the results of preliminary MTT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 6b, 6c, 6d, 6h and 6i is accompanied by low level of cytotoxic concentrations. All the newly synthesized analogues were characterized by IR, H-1 NMR, C-13 NMR and mass spectral data.