1,4-Dimethylbenzimidazole-2-carbaldehyde | 1357162-22-1

• 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: 1,4-Dimethylbenzimidazole-2-carbaldehyde
• 英文别名: 1,4-dimethylbenzimidazole-2-carbaldehyde
• CAS: 1357162-22-1
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: VIVUWIFBQMHMNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-羟基-3-甲氧苯基)-3-丁烯-2-酮 、 1,4-Dimethylbenzimidazole-2-carbaldehyde 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以90%的产率得到
  参考文献：
  名称：

  Cytotoxicity of Substituted Benzimidazolyl Curcumin Mimics Against Multi-Drug Resistance Cancer Cell

  摘要：

  DOI：

  10.5012/bkcs.2013.34.4.1272
• 作为产物：
  描述：

  2,3-二氨基甲苯 在 盐酸 、 四丁基溴化铵 、 戴斯-马丁氧化剂 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 1,4-Dimethylbenzimidazole-2-carbaldehyde
  参考文献：
  名称：

  Synthesis of substituted benzimidazolyl curcumin mimics and their anticancer activity

  摘要：

  A novel curcumin mimic library (14a-14h and 15a-15h) possessing variously substituted benzimidazole groups was synthesized through the aldol reaction of (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (7) or (E)-4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one (13) with diversely substituted benzimidazolyl-2-carbaldehyde (12a-12h). The MTT assay of the cancer cells MCF-7, SH-SY5Y, HEP-G2, and H460 showed that compound 14c with IC50 of 1.0 and 1.9 mu M has a strong inhibitory effect on the growth of SH-SY5Y and Hep-G2 cells, respectively, and that compound 15h with IC50 of 1.9 mu M has a strong inhibitory effect on the growth of MCF-7 cancer cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.074

文献信息

• Synthesis of substituted benzimidazolyl curcumin mimics and their anticancer activity
  作者：Ho Bum Woo、Young Woo Eom、Kyu-Sang Park、Jungyeob Ham、Chan Mug Ahn、Seokjoon Lee

  DOI：10.1016/j.bmcl.2011.12.074

  日期：2012.1

  A novel curcumin mimic library (14a-14h and 15a-15h) possessing variously substituted benzimidazole groups was synthesized through the aldol reaction of (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (7) or (E)-4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one (13) with diversely substituted benzimidazolyl-2-carbaldehyde (12a-12h). The MTT assay of the cancer cells MCF-7, SH-SY5Y, HEP-G2, and H460 showed that compound 14c with IC50 of 1.0 and 1.9 mu M has a strong inhibitory effect on the growth of SH-SY5Y and Hep-G2 cells, respectively, and that compound 15h with IC50 of 1.9 mu M has a strong inhibitory effect on the growth of MCF-7 cancer cells. (C) 2011 Elsevier Ltd. All rights reserved.
• Cytotoxicity of Substituted Benzimidazolyl Curcumin Mimics Against Multi-Drug Resistance Cancer Cell
  作者：Young Woo Eom、Sangtae Oh、Ho Bum Woo、Jungyeob Ham、Chan Mug Ahn、Seokjoon Lee

  DOI：10.5012/bkcs.2013.34.4.1272

  日期：2013.4.20