3-(2-hydroxyethoxy)-4-methoxy-N-(5-(3-(trifluoromethyl)benzoyl)thiazol-2-yl)benzamide | 1081314-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-hydroxyethoxy)-4-methoxy-N-(5-(3-(trifluoromethyl)benzoyl)thiazol-2-yl)benzamide
• 英文别名: 3-(2-hydroxyethoxy)-4-methoxy-N-[5-[3-(trifluoromethyl)benzoyl]-1,3-thiazol-2-yl]benzamide
• CAS: 1081314-11-5
• 化学式: C₂₁H₁₇F₃N₂O₅S
• 分子量: 466.438
• InChiKey: VKQREXCKIKMRDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxyethoxy)-4-methoxy-N-(5-(3-(trifluoromethyl)benzoyl)thiazol-2-yl)benzamide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以48%的产率得到N-(5-(hydroxy(3-(trifluoromethyl)phenyl)methyl)thiazol-2-yl)-3-(2-hydroxyethoxy)-4-methoxybenzamide
  参考文献：
  名称：

  Novel and potent inhibitors of stearoyl-CoA desaturase-1. Part II: Identification of 4-ethylamino-3-(2-hydroxyethoxy)-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide and its biological evaluation

  摘要：

  The continuing investigation of SAR studies of 3-(2-hydroxyethoxy)-N-(5-benzylthiazol-2-yl)-benzamides as stearoyl-CoA desaturase-1 (SCD-1) inhibitors is reported. Our prior hit-to-lead effort resulted in the identification of 1a as a potent and orally efficacious SCD-1 inhibitor. Further optimization of the structural motif resulted in the identification of 4-ethylamino-3-(2-hydroxyethoxy)-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide (37c) with sub nano molar IC(50) in both murine and human SCD-1 inhibitory assays. This compound demonstrated a dose-dependent decrease in the plasma desaturation index in C57BL/6J mice on a non-fat diet after 7 days of oral administration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.123
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 生成 3-(2-hydroxyethoxy)-4-methoxy-N-(5-(3-(trifluoromethyl)benzoyl)thiazol-2-yl)benzamide
  参考文献：
  名称：

  Novel and potent inhibitors of stearoyl-CoA desaturase-1. Part II: Identification of 4-ethylamino-3-(2-hydroxyethoxy)-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide and its biological evaluation

  摘要：

  The continuing investigation of SAR studies of 3-(2-hydroxyethoxy)-N-(5-benzylthiazol-2-yl)-benzamides as stearoyl-CoA desaturase-1 (SCD-1) inhibitors is reported. Our prior hit-to-lead effort resulted in the identification of 1a as a potent and orally efficacious SCD-1 inhibitor. Further optimization of the structural motif resulted in the identification of 4-ethylamino-3-(2-hydroxyethoxy)-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide (37c) with sub nano molar IC(50) in both murine and human SCD-1 inhibitory assays. This compound demonstrated a dose-dependent decrease in the plasma desaturation index in C57BL/6J mice on a non-fat diet after 7 days of oral administration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.123

文献信息

• Novel and potent inhibitors of stearoyl-CoA desaturase-1. Part II: Identification of 4-ethylamino-3-(2-hydroxyethoxy)-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide and its biological evaluation
  作者：Yoshikazu Uto、Tsuneaki Ogata、Yohei Kiyotsuka、Yuriko Miyazawa、Yuko Ueno、Hitoshi Kurata、Tsuneo Deguchi、Makiko Yamada、Nobuaki Watanabe、Toshiyuki Takagi、Satoko Wakimoto、Ryo Okuyama、Masahiro Konishi、Nobuya Kurikawa、Keita Kono、Jun Osumi

  DOI：10.1016/j.bmcl.2009.05.123

  日期：2009.8

  The continuing investigation of SAR studies of 3-(2-hydroxyethoxy)-N-(5-benzylthiazol-2-yl)-benzamides as stearoyl-CoA desaturase-1 (SCD-1) inhibitors is reported. Our prior hit-to-lead effort resulted in the identification of 1a as a potent and orally efficacious SCD-1 inhibitor. Further optimization of the structural motif resulted in the identification of 4-ethylamino-3-(2-hydroxyethoxy)-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide (37c) with sub nano molar IC(50) in both murine and human SCD-1 inhibitory assays. This compound demonstrated a dose-dependent decrease in the plasma desaturation index in C57BL/6J mice on a non-fat diet after 7 days of oral administration. (C) 2009 Elsevier Ltd. All rights reserved.