1-(1H-benzo[d]imidazol-2-yl)-3-(5-mercapto-1,3,4-oxadiazol-2-yl) propan-1-one | 1396319-05-3

• 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-mercapto-1,3,4-oxadiazol-2-yl) propan-1-one
• 英文别名: 1-(1H-benzimidazol-2-yl)-3-(2-sulfanylidene-3H-1,3,4-oxadiazol-5-yl)propan-1-one
• CAS: 1396319-05-3
• 化学式: C₁₂H₁₀N₄O₂S
• 分子量: 274.303
• InChiKey: UIBHAWHRGPMQPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(1H-benzo[d]imidazol-2-yl)-3-(5-mercapto-1,3,4-oxadiazol-2-yl) propan-1-one 在 一水合肼 、 三氯氧磷 作用下， 以 正丁醇 为溶剂， 反应 5.0h， 生成 1-(1H-benzo[d]imidazol-2-yl)-3-(6-styryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-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
• 作为产物：
  描述：

  alpha-酮戊二酸 在 盐酸 、 硫酸 、 一水合肼 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 30.0h， 生成 1-(1H-benzo[d]imidazol-2-yl)-3-(5-mercapto-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 clubbed with triazolo-thiadiazoles and triazolo-thiadiazines: New anticancer agents
  作者：Asif Husain、Mohd Rashid、M. Shaharyar、Anees A. Siddiqui、Ravinesh Mishra

  DOI：10.1016/j.ejmech.2012.07.011

  日期：2013.4

  Two series of Benzimidazole clubbed with triazolo-thiadiazoles (5a-q, 5r, 5s and 5x-a(1)) and triazolo-thiadiazines (5t-w) were synthesized with an aim to produce promising anticancer agents. In vitro anticancer activities of synthesized compounds were investigated at the National Cancer Institute (NCI) against NCI 60 cell line panel; results showed good to remarkable broad-spectrum anticancer activity. Among them, the compound 5h (NCS: 760452, 1-(1H-benzo [d] imidazol-2-yl)-3-(6-(2,4-dichlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl) propan-l-one) exhibited significant growth inhibition with GI(50) values ranging from 0.20 to 2.58 mu M and found superior selectivity for the leukemia cell lines and further screened at 10-fold dilutions of five different concentrations (0.01, 0.1, 1, 10 and 100 mu M). The 5h may possibly be used as lead compound for developing new anticancer agents. (C) 2012 Elsevier Masson SAS. All rights reserved.
• 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.