N-benzyl-2-(2-(4-(2-morpholinoethoxy)phenyl)thiazol-4-yl)acetamide | 1339961-98-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-benzyl-2-(2-(4-(2-morpholinoethoxy)phenyl)thiazol-4-yl)acetamide
• 英文别名: N-benzyl-2-[2-[4-(2-morpholin-4-ylethoxy)phenyl]-1,3-thiazol-4-yl]acetamide
• CAS: 1339961-98-6
• 化学式: C₂₄H₂₇N₃O₃S
• 分子量: 437.563
• InChiKey: WOOXRNLCCADTBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(2-氯乙基)吗啉盐酸盐 在 吡啶 、 ammonium sulfide 、 水 、 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 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 100.5h， 生成 N-benzyl-2-(2-(4-(2-morpholinoethoxy)phenyl)thiazol-4-yl)acetamide
  参考文献：
  名称：

  Thiazolyl N-benzyl-substituted acetamide derivatives: Synthesis, Src kinase inhibitory and anticancer activities

  摘要：

  KX2-391 (KX-01/Kinex Pharmaceuticals), N-benzyl-2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl) acetamide, is a highly selective Src substrate binding site inhibitor. To understand better the role of pyridine ring and N-benzylsubstitution in KX2-391 and establish the structure activity relationship, a number of N-benzyl substituted (((2-morpholinoethoxy)phenyl)thiazol-4-yl)acetamide derivatives containing thiazole instead of pyridine were synthesized and evaluated for Src kinase inhibitory activities. The unsubstituted N-benzyl derivative (8a) showed the inhibition of c-Src kinase with GI(50) values of 1.34 mu M and 2.30 mu M in NIH3T3/c-Src527F and SYF/c-Src527F cells, respectively. All the synthesized compounds were evaluated for inhibition of cell proliferation of human colon carcinoma (HT-29), breast carcinoma (BT-20), and leukemia (CCRF-CEM) cells. 4-Fluorobenzylthiazolyl derivative 8b exhibited 64 -71% inhibition in the cell proliferation of BT-20 and CCRF cells at concentration of 50 mu M. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.050

文献信息

• Thiazolyl N-benzyl-substituted acetamide derivatives: Synthesis, Src kinase inhibitory and anticancer activities
  作者：Asal Fallah-Tafti、Alireza Foroumadi、Rakesh Tiwari、Amir Nasrolahi Shirazi、David G. Hangauer、Yahao Bu、Tahmineh Akbarzadeh、Keykavous Parang、Abbas Shafiee

  DOI：10.1016/j.ejmech.2011.07.050

  日期：2011.10

  KX2-391 (KX-01/Kinex Pharmaceuticals), N-benzyl-2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl) acetamide, is a highly selective Src substrate binding site inhibitor. To understand better the role of pyridine ring and N-benzylsubstitution in KX2-391 and establish the structure activity relationship, a number of N-benzyl substituted (((2-morpholinoethoxy)phenyl)thiazol-4-yl)acetamide derivatives containing thiazole instead of pyridine were synthesized and evaluated for Src kinase inhibitory activities. The unsubstituted N-benzyl derivative (8a) showed the inhibition of c-Src kinase with GI(50) values of 1.34 mu M and 2.30 mu M in NIH3T3/c-Src527F and SYF/c-Src527F cells, respectively. All the synthesized compounds were evaluated for inhibition of cell proliferation of human colon carcinoma (HT-29), breast carcinoma (BT-20), and leukemia (CCRF-CEM) cells. 4-Fluorobenzylthiazolyl derivative 8b exhibited 64 -71% inhibition in the cell proliferation of BT-20 and CCRF cells at concentration of 50 mu M. (C) 2011 Elsevier Masson SAS. All rights reserved.