4-ethylamino-3-(2-hydroxyethoxy)-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide | 1081313-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-ethylamino-3-(2-hydroxyethoxy)-N-[5-(3-trifluoromethylbenzyl)thiazol-2-yl]benzamide
• 英文别名: 4-(ethylamino)-3-(2-hydroxyethoxy)-N-(5-(3-(trifluoromethyl)benzyl)thiazol-2-yl)benzamide；4-(ethylamino)-3-(2-hydroxyethoxy)-N-[5-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-2-yl]benzamide
• CAS: 1081313-90-7
• 化学式: C₂₂H₂₂F₃N₃O₃S
• 分子量: 465.496
• InChiKey: HYWPCURCNVJWBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以61%的产率得到4-ethylamino-3-(2-hydroxyethoxy)-N-[5-(3-trifluoromethylbenzyl)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

• [EN] IMPROVED PEPTIDE PHARMACEUTICALS FOR TREATMENT OF NASH AND OTHER DISORDERS<br/>[FR] COMPOSÉS PHARMACEUTIQUES PEPTIDIQUES AMÉLIORÉS UTILISÉS POUR LE TRAITEMENT D'UNE STÉATOHÉPATITE NON ALCOOLIQUE ET D'AUTRES TROUBLES
  申请人：SPITFIRE PHARMA INC

  公开号：WO2019136158A1

  公开（公告）日：2019-07-11

  The disclosure provides peptide products comprising a peptide covalently attached to a surfactant moiety which have improved properties, including increased duration of action and bioavailability. The peptide products are useful for treating insulin resistance, diabetes, obesity, metabolic syndrome and cardiovascular diseases, and conditions associated therewith, such as NASH and PCOS.

  该披露提供了包括肽共价连接到表面活性剂基团的肽产品，具有改善的特性，包括增加作用持续时间和生物利用度。这些肽产品可用于治疗胰岛素抵抗、糖尿病、肥胖、代谢综合征和心血管疾病，以及相关的疾病，如NASH和PCOS。
• IMPROVED PEPTIDE PHARMACEUTICALS FOR TREATMENT OF NASH AND OTHER DISORDERS
  申请人：Mederis Diabetes, LLC

  公开号：EP3735295A1

  公开（公告）日：2020-11-11
• GLP-1R and GCGR Agonists, Formulations, and Methods of Use
  申请人：Spitfire Pharma LLC

  公开号：US20210290732A1

  公开（公告）日：2021-09-23

  This disclosure relates to the field of GLP-1R and GCGR agonists, formulations, and methods of using the same, including but not limited to dual agonist peptides of any of SEQ ID NOS. 1-10 or 12-27 conjugated to a non-ionic glycolipid surfactant.
• 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.