ethyl 2-(2-(4-(2-morpholinoethoxy)phenyl)thiazol-4-yl)acetate | 1339961-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 2-(2-(4-(2-morpholinoethoxy)phenyl)thiazol-4-yl)acetate
• 英文别名: Ethyl 2-[2-[4-(2-morpholin-4-ylethoxy)phenyl]-1,3-thiazol-4-yl]acetate
• CAS: 1339961-97-5
• 化学式: C₁₉H₂₄N₂O₄S
• 分子量: 376.477
• InChiKey: HJBGIROLRDLDTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-(4-(2-morpholinoethoxy)phenyl)thiazol-4-yl)acetate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以42%的产率得到2-(2-(4-(2-morpholinoethoxy)phenyl)thiazol-4-yl)acetic acid
  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
• 作为产物：
  描述：

  N-(2-氯乙基)吗啉盐酸盐 在 吡啶 、 ammonium sulfide 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 ethyl 2-(2-(4-(2-morpholinoethoxy)phenyl)thiazol-4-yl)acetate
  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.