1-(1H-benzimidazol-2-yl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one | 36998-76-2

• 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-(3,4,5-trimethoxyphenyl)-2-propen-1-one
• 英文别名: 1-(1H-benzo[d]imidazol-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；1-(1H-Benzimidazol-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；1-(1H-benzimidazol-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 36998-76-2
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: UXOHHJOGSGNKCX-UHFFFAOYSA-N

物化性质

• 熔点：
  217 °C(Solv: ethanol (64-17-5))
• 沸点：
  569.7±60.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(1H-benzimidazol-2-yl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 2-(4,5-dihydro-5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Nofal, Zienab M.; Soliman, Elsyed A.; Abd El-Karim, Somaia S., Acta poloniae pharmaceutica, 2011, vol. 68, # 4, p. 519 - 534

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(1-羟乙基)苯并咪唑 在 potassium dichromate 、 硫酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 1-(1H-benzimidazol-2-yl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Synthesis, characterization, and antimicrobial activity of benzimidazole-derived chalcones containing 1,3,4-oxadiazole moiety

  摘要：

  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.

  DOI：

  10.1007/s10593-015-1653-1

文献信息

• 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
• Rajora, Jayanti; Yadav, Janardan; Kumar, Ravindra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 7, p. 989 - 993
  作者：Rajora, Jayanti、Yadav, Janardan、Kumar, Ravindra、Srivastava, Yogendra K.

  DOI：——

  日期：——
• Nofal, Zienab M.; Soliman, Elsyed A.; Abd El-Karim, Somaia S., Acta poloniae pharmaceutica, 2011, vol. 68, # 4, p. 519 - 534
  作者：Nofal, Zienab M.、Soliman, Elsyed A.、Abd El-Karim, Somaia S.、El-Zahar, Magdy I.、Srour, Aladdin M.、Sethumadhavan, Shalini、Maher, Timothy J.

  DOI：——

  日期：——
• 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.