N-(4-benzyloxypyridin-2-yl)-3-phenylpropionamide | 1415834-60-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-benzyloxypyridin-2-yl)-3-phenylpropionamide
• 英文别名: 3-phenyl-N-(4-phenylmethoxypyridin-2-yl)propanamide
• CAS: 1415834-60-4
• 化学式: C₂₁H₂₀N₂O₂
• 分子量: 332.402
• InChiKey: IUKPKVOEVBFMAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-硝基吡啶-N-氧化物 在 4-二甲氨基吡啶 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 对甲苯磺酰氯 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 89.17h， 生成 N-(4-benzyloxypyridin-2-yl)-3-phenylpropionamide
  参考文献：
  名称：

  Rational design and synthesis of 4-substituted 2-pyridin-2-ylamides with inhibitory effects on SH2 domain-containing inositol 5′-phosphatase 2 (SHIP2)

  摘要：

  Novel 4-substituted 2-pyridin-2-ylamides were developed using in-silico ligand-based drug design (LBDD) in an attempt to identify inhibitors of SH2-containing 5'-inositol phosphatase 2 (SHIP2), which is implicated in insulin-resistant type 2 diabetes. Among the compounds synthesized, N-[4-(4-chlorobenzyloxy) pyridin-2-yl]-2-(2,6-difluorophenyl)- acetamide (CPDA, 4a) was identified as a potent SHIP2 inhibitor. CPDA was found to enhance in vitro insulin signaling through the Akt pathway more efficiently than the previously reported SHIP2 inhibitor AS1949490, and ameliorated abnormal glucose metabolism in diabetic (db/db) mice. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.014

文献信息

• [EN] NOVEL N-(PYRIDIN-2-YL)ALKANAMIDE DERIVATIVE AND SHIP2 INHIBITOR CONTAINING SAME AS AN ACTIVE INGREDIENT<br/>[FR] NOUVEAU DÉRIVÉ DE N-(PYRIDIN-2-YL)ALCANAMIDE ET INHIBITEUR DE SHIP2 CONTENANT CELUI-CI EN TANT QUE SUBSTANCE ACTIVE
  申请人：NAT UNIV CORP UNIV TOYAMA

  公开号：WO2012169571A1

  公开（公告）日：2012-12-13

  【課題】新規なＮ－（ピリジン－２－イル）アルカンアミド誘導体およびそれらを有効成分とする新規なインスリン抵抗性改善薬を提供する。 【解決手段】 上記一般式［１ａ］において、Ｒ１およびＲ２ａが水素原子またはハロゲン原子、Ａがアルキレン基または結合で表される新規なＮ－（ピリジン－２－イル）フェニルアルカンアミド誘導体またはその塩は、ＳＨＩＰ２の阻害作用を有し、インスリン感受性を増加させることから、インスリン抵抗性改善薬として有用である。
• Rational design and synthesis of 4-substituted 2-pyridin-2-ylamides with inhibitory effects on SH2 domain-containing inositol 5′-phosphatase 2 (SHIP2)
  作者：Yoshinori Ichihara、Ryohei Fujimura、Hiroshi Tsuneki、Tsutomu Wada、Kentaro Okamoto、Hiroaki Gouda、Shuichi Hirono、Kenji Sugimoto、Yuji Matsuya、Toshiyasu Sasaoka、Naoki Toyooka

  DOI：10.1016/j.ejmech.2013.01.014

  日期：2013.4

  Novel 4-substituted 2-pyridin-2-ylamides were developed using in-silico ligand-based drug design (LBDD) in an attempt to identify inhibitors of SH2-containing 5'-inositol phosphatase 2 (SHIP2), which is implicated in insulin-resistant type 2 diabetes. Among the compounds synthesized, N-[4-(4-chlorobenzyloxy) pyridin-2-yl]-2-(2,6-difluorophenyl)- acetamide (CPDA, 4a) was identified as a potent SHIP2 inhibitor. CPDA was found to enhance in vitro insulin signaling through the Akt pathway more efficiently than the previously reported SHIP2 inhibitor AS1949490, and ameliorated abnormal glucose metabolism in diabetic (db/db) mice. (C) 2013 Elsevier Masson SAS. All rights reserved.