2-(2-(4-(2-morpholinoethoxy)phenyl)thiazol-4-yl)acetic acid | 938364-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-(4-(2-morpholinoethoxy)phenyl)thiazol-4-yl)acetic acid
• 英文别名: 2-[2-[4-(2-morpholin-4-ium-4-ylethoxy)phenyl]-1,3-thiazol-4-yl]acetate
• CAS: 938364-87-5
• 化学式: C₁₇H₂₀N₂O₄S
• 分子量: 348.423
• InChiKey: QJJCTAMZJYXZQW-UHFFFAOYSA-N

物化性质

• 沸点：
  569.2±60.0 °C(predicted)
• 密度：
  1.290±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-(4-(2-morpholinoethoxy)phenyl)thiazol-4-yl)acetic acid 、 4-甲基苄胺 在 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 乙腈 为溶剂， 反应 24.5h， 以18%的产率得到N-(4-methylbenzyl)-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
• 作为产物：
  描述：

  N-(2-氯乙基)吗啉盐酸盐 在 吡啶 、 ammonium sulfide 、 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 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