N1-(4-methyl-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide | 1392442-21-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N1-(4-methyl-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide
• 英文别名: N-(4-methyl-1,3-benzothiazol-2-yl)-2-(2-methoxy-5-((Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl)phenoxy)acetamide；2-[2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenoxy]-N-(4-methyl-1,3-benzothiazol-2-yl)acetamide
• CAS: 1392442-21-5
• 化学式: C₂₈H₂₈N₂O₆S
• 分子量: 520.606
• InChiKey: CXWVVDRSJSMGON-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (Z)-3,4,5,4',-四甲氧基-3'-羟基二苯乙烯 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 60.0h， 生成 N1-(4-methyl-1,3-benzothiazol-2-yl)-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of combretastatin-amidobenzothiazole conjugates as potential anticancer agents

  摘要：

  A series of combretastatin-amidobenzothiazole conjugates have been synthesized and evaluated for their anticancer activity. All these compounds exhibited significant anticancer activity and the most potent compound (11a) showed GI(50) values ranging 0.019-11 mu M. Biological studies such as cell cycle distribution, effect on tubulin polymerization and effect on ERK signalling pathway have been examined in MCF-7 cell line. FACS analysis revealed that these compounds induced cell cycle arrest at G2/M phase. Compound ha showed significant effect on tubulin polymerization and affected the ERK signalling pathway that result in the decreased levels of ERK1/2, p-ERR and c-Jun proteins. Docking experiments have shown that the active molecules interact and bind well in the ATP binding pocket of ERR protein. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.021

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 and biological evaluation of combretastatin-amidobenzothiazole conjugates as potential anticancer agents
  作者：Ahmed Kamal、Adla Mallareddy、M. Janaki Ramaiah、S.N.C.V.L. Pushpavalli、Paidakula Suresh、Chandan Kishor、J.N.S.R.C. Murty、N. Sankara Rao、Sowjanya Ghosh、Anthony Addlagatta、Manika Pal-Bhadra

  DOI：10.1016/j.ejmech.2012.08.021

  日期：2012.10

  A series of combretastatin-amidobenzothiazole conjugates have been synthesized and evaluated for their anticancer activity. All these compounds exhibited significant anticancer activity and the most potent compound (11a) showed GI(50) values ranging 0.019-11 mu M. Biological studies such as cell cycle distribution, effect on tubulin polymerization and effect on ERK signalling pathway have been examined in MCF-7 cell line. FACS analysis revealed that these compounds induced cell cycle arrest at G2/M phase. Compound ha showed significant effect on tubulin polymerization and affected the ERK signalling pathway that result in the decreased levels of ERK1/2, p-ERR and c-Jun proteins. Docking experiments have shown that the active molecules interact and bind well in the ATP binding pocket of ERR protein. (C) 2012 Elsevier Masson SAS. All rights reserved.