1-(1H-benzimidazol-2-yl)-3-(3-methoxyphenyl)-2-propen-1-one | 145126-34-7

• 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: 1-(1H-benzimidazol-2-yl)-3-(3-methoxyphenyl)-2-propen-1-one
• 英文别名: (E)-1-(2-Benzimidazolyl)-3-(3-methoxyphenyl)-2-propen-1-one；1-(1H-benzimidazol-2-yl)-3-(3-methoxyphenyl)prop-2-en-1-one
• CAS: 145126-34-7
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: LYIXYIZJQVGZQG-UHFFFAOYSA-N

物化性质

• 沸点：
  521.3±53.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.98
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(1H-benzimidazol-2-yl)-3-(3-methoxyphenyl)-2-propen-1-one 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-(3-methoxyphenyl)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-benzimidazol-2-yl)-3-(3-methoxyphenyl)-2-propen-1-one
  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 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。
• Synthesis, characterization, and antimicrobial activity of benzimidazole-derived chalcones containing 1,3,4-oxadiazole moiety
  作者：Gangadhar A. Meshram、Vipul A. Vala

  DOI：10.1007/s10593-015-1653-1

  日期：2015.1

  A series of novel benzimidazole-derived chalcones containing the 1,3,4-oxadiazole moiety were synthesized and characterized by IR, H-1, C-13 NMR, and mass spectra and elemental analysis. The synthesized compounds were evaluated for their efficiency as antibacterial agents against two Gram-positive and Gram-negative strains of bacteria along with antifungal activity against three fungal species. Antibacterial activity revealed that tested compounds exhibited potent activity whereas some compounds exhibited moderate antifungal activity as compared to the standards.
• 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.
• Design and structure-activity relationships anticandidosic of diazaheteroaryl functionalized by Michaël acceptors
  作者：Songuigama Coulibaly、Jean-Paul NGuessan Deto、Aboudramane Koné、Doumadé Zon、Mamidou Witabouna Koné、Drissa Sissouma、Mahama Ouattara

  DOI：10.21608/ejchem.2021.87021.4207

  日期：2021.9.20

  The management of candidiasis, once effective, is becoming more and more difficult with the increase of resistance of various Candida species to classical antifungals. It is in this context that we reported in our previous works the pharmacochemical development of new diazaheteroaryls derivatives functionalized with a Michaël acceptor such as arylpropenone, arylacrylonitrile and arylcyanopropenone. These diazaheteroaryls derivatives with benzimidazolyl-arylpropenone or benzimidazolyl-arylacrylonitriles or benzimidazolyl-arylcyanopropenone and imidazopyridinyl-arylpropenones structure were obtained by chemical synthesis and then characterized by the usual spectroscopic methods (NMR and MS). The anticandidosic activities of these derivatives expressed as Minimum Inhibitory Quantity (MIQ) were determined in vitro on a clinical strain of Candida albicans, following the bioautography technique. The results show that diazaheteroaryls functionalized by a Michael acceptor have remarkable activities with IMQ ranging from 10 to 0.16 µg. Moreover, the anticandidosic performance of the different derivatives were related to the nature of the Michael acceptor and the structural variations undertaken on the benzene homocycle. This paper, which is the synthesis of a decade of research by our team, will address the pharmacochemical design, chemical synthesis and overall serial structure-anticandidosic activity studies of diaza-heteroaryls functionalized with a Michael acceptor in order to propose compounds that can be developed as anticandidosic drug candidates.

  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。