1-(1H-benzimidazol-2-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one | 145126-45-0

• 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-benzimidazol-2-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
• CAS: 145126-45-0
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: PJMQJMAPCQJAGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  22.0
• 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：
  75.21
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(1H-benzimidazol-2-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-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 28.0h， 生成 6-(1H-benzo[d]imidazol-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-2-(2-(3-nitrophenyl)-4-oxothiazolidin-3-yl)nicotinonitrile
  参考文献：
  名称：

  Synthesis, antimicrobial, and cytotoxic activities of novel benzimidazole derivatives bearing cyanopyridine and 4-thiazolidinone motifs

  摘要：

  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.

  DOI：

  10.1007/s00044-014-0971-7
• 作为产物：
  描述：

  香草醛 、 2-乙酰苯并咪唑 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 1-(1H-benzimidazol-2-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, antimicrobial, and cytotoxic activities of novel benzimidazole derivatives bearing cyanopyridine and 4-thiazolidinone motifs

  摘要：

  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.

  DOI：

  10.1007/s00044-014-0971-7

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, 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.