1-(1H-benzo[d]imidazol-2-yl)-3-(5-(trichloromethyl)-1,3,4-oxadiazol-2-yl)propan-1-one | 1396319-11-1

• 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-(1H-benzo[d]imidazol-2-yl)-3-(5-(trichloromethyl)-1,3,4-oxadiazol-2-yl)propan-1-one
• 英文别名: 1-(1H-benzimidazol-2-yl)-3-[5-(trichloromethyl)-1,3,4-oxadiazol-2-yl]propan-1-one
• CAS: 1396319-11-1
• 化学式: C₁₃H₉Cl₃N₄O₂
• 分子量: 359.599
• InChiKey: ZQMODYZTISIQNS-UHFFFAOYSA-N

物化性质

• 沸点：
  517.2±60.0 °C(Predicted)
• 密度：
  1.602±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  alpha-酮戊二酸 在 盐酸 、 硫酸 、 一水合肼 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 1-(1H-benzo[d]imidazol-2-yl)-3-(5-(trichloromethyl)-1,3,4-oxadiazol-2-yl)propan-1-one
  参考文献：
  名称：

  Benzimidazole bearing oxadiazole and triazolo-thiadiazoles nucleus: Design and synthesis as anticancer agents

  摘要：

  Two new series of benzimidazole bearing oxadiazole[1-(1H-benzo[d]imidazol-2-yl)-3-(5-substituted-1,3,4-oxadiazol-2-yl)propan-1-ones (4a-l)] and triazolo-thiadiazoles[1-(1H-benzo[d]imidazol-2-yl)-3-(6-(substituted)-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazol-3-yl)propan-1-one (7a-e)] have been synthesized successfully from4-(1H-benzo[d]imidazol-2-yl)-4-oxobutanehydrazide (3) with an aim to produce promising anticancer agents. In vitro anticancer activities of synthesized compounds were screened at the National Cancer Institute (NCI), USA, according to their applied protocol against full NCI 60 human cell lines panel; results showed good to remarkable anticancer activity. Among them, compound (4j, NCS: 761980) exhibited significant growth inhibition and further screened at 10-fold dilutions of five different concentrations (0.01, 0.1, 1, 10 and 100 mu M) with GI(50) values ranging from 0.49 to 48.0 mu M and found superior for the non-small cell lung cancer cell lines like HOP-92 (GI(50) 0.49, TGI 19.9, LC50 > 100 and Log(10)GI(50) -6.30, Log(10)TGI -4.70, Log(10)LC(50) >-4.00). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.038

文献信息

• Benzimidazole bearing oxadiazole and triazolo-thiadiazoles nucleus: Design and synthesis as anticancer agents
  作者：Asif Husain、Mohd Rashid、Ravinesh Mishra、Shama Parveen、Dong-Soo Shin、Deepak Kumar

  DOI：10.1016/j.bmcl.2012.07.038

  日期：2012.9

  Two new series of benzimidazole bearing oxadiazole[1-(1H-benzo[d]imidazol-2-yl)-3-(5-substituted-1,3,4-oxadiazol-2-yl)propan-1-ones (4a-l)] and triazolo-thiadiazoles[1-(1H-benzo[d]imidazol-2-yl)-3-(6-(substituted)-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazol-3-yl)propan-1-one (7a-e)] have been synthesized successfully from4-(1H-benzo[d]imidazol-2-yl)-4-oxobutanehydrazide (3) with an aim to produce promising anticancer agents. In vitro anticancer activities of synthesized compounds were screened at the National Cancer Institute (NCI), USA, according to their applied protocol against full NCI 60 human cell lines panel; results showed good to remarkable anticancer activity. Among them, compound (4j, NCS: 761980) exhibited significant growth inhibition and further screened at 10-fold dilutions of five different concentrations (0.01, 0.1, 1, 10 and 100 mu M) with GI(50) values ranging from 0.49 to 48.0 mu M and found superior for the non-small cell lung cancer cell lines like HOP-92 (GI(50) 0.49, TGI 19.9, LC50 > 100 and Log(10)GI(50) -6.30, Log(10)TGI -4.70, Log(10)LC(50) >-4.00). (C) 2012 Elsevier Ltd. All rights reserved.