N-(6-acetylbenzo[d][1,3]dioxol-5-yl)selenophene-2-carboxamide | 1032315-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-(6-acetylbenzo[d][1,3]dioxol-5-yl)selenophene-2-carboxamide
• 英文别名: N-(5-acetylbenzo[d][1,3]dioxol-6-yl)selenophene-2-carboxamide；N-(6-acetyl-1,3-benzodioxol-5-yl)selenophene-2-carboxamide
• CAS: 1032315-83-5
• 化学式: C₁₄H₁₁NO₄Se
• 分子量: 336.206
• InChiKey: JAFSQOZJLSKULO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(6-acetylbenzo[d][1,3]dioxol-5-yl)selenophene-2-carboxamide 在 sodium hydroxide 、 氯化铵 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.5h， 以58.6%的产率得到6,7-methylenedioxy-2-(selenophen-2-yl)quinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs

  摘要：

  6,7-Methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-ones and their isosteric compounds were synthesized and evaluated for anticancer activity. Structure activity relationships (SAR) of these compounds were established. Among all tested compounds, 6,7-methylenedioxy-2-(5-methylselenophen-2-yl)quinolin-4-one (4d) was found to be the most promising anticancer agent. In screening against NCI's 60 human tumor cell line panel, 4d exhibited highly selective and potent inhibitory activity against MDA-MB-435 melanoma. Furthermore, the results of COMPARE analysis suggested that 4d is an antimitotic agent with a different mechanism of action from the conventional antimitotic agents, such as colchicine, vinca alkaloids and paclitaxel. Therefore, 4d was identified as a new lead compound that merits further optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.017
• 作为产物：
  描述：

  硒吩-2-羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 23.0h， 生成 N-(6-acetylbenzo[d][1,3]dioxol-5-yl)selenophene-2-carboxamide
  参考文献：
  名称：

  WO2008/70176

  摘要：

  公开号：

文献信息

• WO2008/70176
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs
  作者：Chien-Ting Chen、Mei-Hua Hsu、Yung-Yi Cheng、Chin-Yu Liu、Li-Chen Chou、Li-Jiau Huang、Tian-Shung Wu、Xiaoming Yang、Kuo-Hsiung Lee、Sheng-Chu Kuo

  DOI：10.1016/j.ejmech.2011.10.017

  日期：2011.12

  6,7-Methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-ones and their isosteric compounds were synthesized and evaluated for anticancer activity. Structure activity relationships (SAR) of these compounds were established. Among all tested compounds, 6,7-methylenedioxy-2-(5-methylselenophen-2-yl)quinolin-4-one (4d) was found to be the most promising anticancer agent. In screening against NCI's 60 human tumor cell line panel, 4d exhibited highly selective and potent inhibitory activity against MDA-MB-435 melanoma. Furthermore, the results of COMPARE analysis suggested that 4d is an antimitotic agent with a different mechanism of action from the conventional antimitotic agents, such as colchicine, vinca alkaloids and paclitaxel. Therefore, 4d was identified as a new lead compound that merits further optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.