(E)-2-(2-methoxy-5-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl)phenoxy)-N-(6-chlorobenzo[d]thiazol-2-yl)acetamide | 1379509-94-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2-(2-methoxy-5-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl)phenoxy)-N-(6-chlorobenzo[d]thiazol-2-yl)acetamide
• 英文别名: N1-(6-chloro-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)-1-propenyl]phenoxy}acetamide；N-(6-chloro-1,3-benzothiazol-2-yl)-2-[2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]phenoxy]acetamide
• CAS: 1379509-94-0
• 化学式: C₂₈H₂₅ClN₂O₇S
• 分子量: 569.035
• InChiKey: FDJQUCZAGMUUGO-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (E)-3-(3-hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 lithium hydroxide monohydrate 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (E)-2-(2-methoxy-5-(3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl)phenoxy)-N-(6-chlorobenzo[d]thiazol-2-yl)acetamide
  参考文献：
  名称：

  Synthesis of chalcone-amidobenzothiazole conjugates as antimitotic and apoptotic inducing agents

  摘要：

  A series of chalcone-amidobenzothiazole conjugates (9a-k and 10a,b) have been synthesized and evaluated for their anticancer activity. All these compounds exhibited potent activity and the IC50 of two potential compounds (9a and 9f) against different cancer cell lines are in the range of 0.85-3.3 mu M. Flow cytometric analysis revealed that these compounds induced cell cycle arrest at G2/M phase in A549 cell line leading to caspase-3 dependent apoptotic cell death. The tubulin polymerization assay (IC50 of 9a is 3.5 mu M and 9f is 5.2 mu M) and immuofluorescence analysis showed that these compounds effectively inhibit microtubule assembly at both molecular and cellular levels in A549 cells. Further, Annexin staining also suggested that these compounds induced cell death by apoptosis. Moreover, docking experiments have shown that they interact and bind efficiently with tubulin protein. Overall, the current study demonstrates that the synthesis of chalcone-amidobenzothiazole conjugates as promising anticancer agents with potent G2/M arrest and apoptotic-inducing activities via targeting tubulin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.010

文献信息

• AMIDOBENZOTHIAZOLES AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Council of Scientific and Industrial Research

  公开号：EP2670740B1

  公开（公告）日：2015-12-30
• US9102638B2
  申请人：——

  公开号：US9102638B2

  公开（公告）日：2015-08-11
• Synthesis of chalcone-amidobenzothiazole conjugates as antimitotic and apoptotic inducing agents
  作者：Ahmed Kamal、Adla Mallareddy、Paidakula Suresh、Thokhir B. Shaik、V. Lakshma Nayak、Chandan Kishor、Rajesh V.C.R.N.C. Shetti、N. Sankara Rao、Jaki R. Tamboli、S. Ramakrishna、Anthony Addlagatta

  DOI：10.1016/j.bmc.2012.04.010

  日期：2012.6

  A series of chalcone-amidobenzothiazole conjugates (9a-k and 10a,b) have been synthesized and evaluated for their anticancer activity. All these compounds exhibited potent activity and the IC50 of two potential compounds (9a and 9f) against different cancer cell lines are in the range of 0.85-3.3 mu M. Flow cytometric analysis revealed that these compounds induced cell cycle arrest at G2/M phase in A549 cell line leading to caspase-3 dependent apoptotic cell death. The tubulin polymerization assay (IC50 of 9a is 3.5 mu M and 9f is 5.2 mu M) and immuofluorescence analysis showed that these compounds effectively inhibit microtubule assembly at both molecular and cellular levels in A549 cells. Further, Annexin staining also suggested that these compounds induced cell death by apoptosis. Moreover, docking experiments have shown that they interact and bind efficiently with tubulin protein. Overall, the current study demonstrates that the synthesis of chalcone-amidobenzothiazole conjugates as promising anticancer agents with potent G2/M arrest and apoptotic-inducing activities via targeting tubulin. (C) 2012 Elsevier Ltd. All rights reserved.