(+/-)-2-((E)-3-(3-chlorophenyl)acrylamido)-3-(2-(2-fluorobenzyloxy)naphthalen-6-yl)propanoic acid | 1334953-21-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-2-((E)-3-(3-chlorophenyl)acrylamido)-3-(2-(2-fluorobenzyloxy)naphthalen-6-yl)propanoic acid
• 英文别名: 2-[[(E)-3-(3-chlorophenyl)prop-2-enoyl]amino]-3-[6-[(2-fluorophenyl)methoxy]naphthalen-2-yl]propanoic acid
• CAS: 1334953-21-7
• 化学式: C₂₉H₂₃ClFNO₄
• 分子量: 503.957
• InChiKey: ZEYATNRWXGLTLA-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Methyl 2-amino-3-(6-hydroxynaphthalen-2-yl)propanoate;hydrochloride 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 sodium hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 16.0h， 生成 (+/-)-2-((E)-3-(3-chlorophenyl)acrylamido)-3-(2-(2-fluorobenzyloxy)naphthalen-6-yl)propanoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of (±)-3-(2-(2-fluorobenzyloxy) naphthalen-6-yl)-2-aminopropanoic acid derivatives as novel PTP1B inhibitors

  摘要：

  A series of novel nonphosphonate-based pTyr mimetics comprised (+/-)-3-(2-(2-fluorobenzyloxy)naphthalen-6-yl)-2-aminopropanoic acid derivatives were identified as reversible and competitive PTP1B inhibitors via a structure-based design approach. Among the compounds studied, 12h was found to have the best in vitro inhibition activity against PTP1B (IC(50) = 1.25 +/- 0.24 mu M) and the best selectivity (3-fold) between PTP1B and TCPTP. These results should provide suitable druglike lead compounds for the design of inhibitors of PTP1B as well as other PTPs. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.027

文献信息

• Synthesis and biological evaluation of (±)-3-(2-(2-fluorobenzyloxy) naphthalen-6-yl)-2-aminopropanoic acid derivatives as novel PTP1B inhibitors
  作者：Liang-Peng Sun、Qiang Shen、Hong-Hua Piao、Wei-Ping Ma、Li-Xin Gao、Wei Zhang、Fa-Jun Nan、Jia Li、Hu-Ri Piao

  DOI：10.1016/j.ejmech.2011.05.027

  日期：2011.9

  A series of novel nonphosphonate-based pTyr mimetics comprised (+/-)-3-(2-(2-fluorobenzyloxy)naphthalen-6-yl)-2-aminopropanoic acid derivatives were identified as reversible and competitive PTP1B inhibitors via a structure-based design approach. Among the compounds studied, 12h was found to have the best in vitro inhibition activity against PTP1B (IC(50) = 1.25 +/- 0.24 mu M) and the best selectivity (3-fold) between PTP1B and TCPTP. These results should provide suitable druglike lead compounds for the design of inhibitors of PTP1B as well as other PTPs. (C) 2011 Elsevier Masson SAS. All rights reserved.