2-(4-(3-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)propyl)piperazin-1-yl)benzo[d]oxazole | 1423160-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-(4-(3-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)propyl)piperazin-1-yl)benzo[d]oxazole
• 英文别名: 2-[4-[3-[[5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]propyl]piperazin-1-yl]-1,3-benzoxazole；2-[4-[3-[[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]propyl]piperazin-1-yl]-1,3-benzoxazole
• CAS: 1423160-45-5
• 化学式: C₂₂H₂₂ClN₅O₂S
• 分子量: 455.968
• InChiKey: YSVJFPZOHSKGRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  96.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-氯苯并恶唑 在 potassium fluoride on basic alumina 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.83h， 生成 2-(4-(3-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)propyl)piperazin-1-yl)benzo[d]oxazole
  参考文献：
  名称：

  Synthesis of piperazinyl benzothiazole/benzoxazole derivatives coupled with 1,3,4-oxadiazole-2-thiol: novel hybrid heterocycles as anticancer agents

  摘要：

  The synthesis of a series of substituted 2-(piperazin-1-yl)benzothiazole/benzoxazole coupled with 1,3,4-oxadiazole-2-thiol pharmacophore (8a-t) is described using a three carbon spacer (Jones and Helm, Drugs 69:1903-1910, 2009). The structures of the compounds were confirmed by NMR and mass spectral data. All the synthesized compounds have been evaluated for their cytotoxicity towards five human cancer cell lines of different origins, viz. MCF-7 (Breast), HeLa (Cervical), HepG(2) (Liver), A431 (Skin) and A549 (Lung), and IC50 values were determined. Among the compounds tested, 8j and 8t displayed maximum cytotoxic activity. A431 was the most sensitive cell line against the compounds studied, followed by MCF7, A549, HepG(2) and HeLa.

  DOI：

  10.1007/s00044-013-0510-y

文献信息

• Synthesis of piperazinyl benzothiazole/benzoxazole derivatives coupled with 1,3,4-oxadiazole-2-thiol: novel hybrid heterocycles as anticancer agents
  作者：M. S. R. Murty、B. Ramalingeswara Rao、Mohana Rao Katiki、Lekshmi R. Nath、Ruby John Anto

  DOI：10.1007/s00044-013-0510-y

  日期：2013.10

  The synthesis of a series of substituted 2-(piperazin-1-yl)benzothiazole/benzoxazole coupled with 1,3,4-oxadiazole-2-thiol pharmacophore (8a-t) is described using a three carbon spacer (Jones and Helm, Drugs 69:1903-1910, 2009). The structures of the compounds were confirmed by NMR and mass spectral data. All the synthesized compounds have been evaluated for their cytotoxicity towards five human cancer cell lines of different origins, viz. MCF-7 (Breast), HeLa (Cervical), HepG(2) (Liver), A431 (Skin) and A549 (Lung), and IC50 values were determined. Among the compounds tested, 8j and 8t displayed maximum cytotoxic activity. A431 was the most sensitive cell line against the compounds studied, followed by MCF7, A549, HepG(2) and HeLa.