1,5-二甲基-1H-苯并咪唑-2-甲醛 | 37735-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1,5-二甲基-1H-苯并咪唑-2-甲醛
• 英文名称: 1.5-Dimethyl-2-benz-imidazolcarboxaldehyd
• 英文别名: 1,5-Dimethyl-2-formylbenzimidazol；1,5-dimethyl-1H-benzoimidazole-2-carbaldehyde；1,5-dimethyl-2-formylbenzimidazole；1,5-Dimethyl-1H-benzo[d]imidazole-2-carbaldehyde；1,5-dimethylbenzimidazole-2-carbaldehyde
• CAS: 37735-10-7
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: VEXXAAIEBLPRLB-UHFFFAOYSA-N

物化性质

• 沸点：
  347.1±35.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

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 、 1,5-二甲基-1H-苯并咪唑-2-甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以58%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：

  (6-甲基-1H-苯并咪唑-2-基)甲醇 在 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 为溶剂， 反应 6.0h， 生成 1,5-二甲基-1H-苯并咪唑-2-甲醛
  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

• New ( E )-1-alkyl-1 H -benzo[ d ]imidazol-2-yl)methylene)indolin-2-ones: Synthesis, in vitro cytotoxicity evaluation and apoptosis inducing studies
  作者：Pankaj Sharma、Dinesh Thummuri、T. Srinivasa Reddy、Kishna Ram Senwar、V.G.M. Naidu、Gannoju Srinivasulu、Suresh K. Bharghava、Nagula Shankaraiah

  DOI：10.1016/j.ejmech.2016.07.019

  日期：2016.10

  A new series of (E)-benzo[d]imidazol-2-yl)methylene)indolin-2-one derivatives has been synthesized and evaluated for their in vitro cytotoxic activity against a panel of selected human cancer cell lines of prostate (PC-3 and DU-145) and breast (BT-549, MDA-MB-231, MCF-7, 4T1), non-small lung (A549) and gastric (HGC) cancer cells along with normal breast epithelial cells (MCF10A). Among the tested compounds, 81 showed significant cytotoxic activity against MDA-MB-231 and 4T1 cancer cells with IC50 values of 3.26 +/- 0.24 mu M and 5.96 +/- 0.67 mu M respectively. The compounds 8f, 8i, 8l and 8o were also screened on normal human breast epithelial cells (MCF10A) and found to be safer with lesser cytotoxicity. The treatment of MDA-MB-231 cells with 81 led to inhibition of cell migration ability through disruption of F-actin protein assembly. The flow-cytometry analysis reveals that the cells arrested in G0/G1 phase of the cell cycle. Further, the compound 81 induced apoptosis of MDA-MB-231 cells was characterized by different staining techniques such as Acridine Orange/Ethidium Bromide (AO/EB), DAPI, annexin V-FITC/PI, Rhodamine-123 and MitoSOX red assay. Western blot studies demonstrated that the compound 81 treatment led to activation of caspase-3, increased expression of cleaved PARP, increased expression of pro-apoptotic Bax and decreased expression of anti-apoptotic Bcl-2 in MDA-MB-231 cancer cells. (C) 2016 Elsevier Masson SAS. All rights reserved.
• US4826833A
  申请人：——

  公开号：US4826833A

  公开（公告）日：1989-05-02
• US5015473A
  申请人：——

  公开号：US5015473A

  公开（公告）日：1991-05-14
• 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