(+/-)-N-tert-butoxycarbonyl-3-(2-(2-fluorobenzyloxy)naphthalen-6-yl)alanine | 1334953-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-N-tert-butoxycarbonyl-3-(2-(2-fluorobenzyloxy)naphthalen-6-yl)alanine
• 英文别名: 3-[6-[(2-Fluorophenyl)methoxy]naphthalen-2-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 1334953-08-0
• 化学式: C₂₅H₂₆FNO₅
• 分子量: 439.484
• InChiKey: KTPGBFFPUBAEBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-N-tert-butoxycarbonyl-3-(2-(2-fluorobenzyloxy)naphthalen-6-yl)alanine 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 (+/-)-3-(2-(2-fluorobenzyloxy)naphthalen-6-yl)-2-((E)-cinnamamido)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
• 作为产物：
  描述：

  Methyl 2-amino-3-(6-hydroxynaphthalen-2-yl)propanoate;hydrochloride 在 potassium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 、 乙腈 为溶剂， 反应 9.0h， 生成 (+/-)-N-tert-butoxycarbonyl-3-(2-(2-fluorobenzyloxy)naphthalen-6-yl)alanine
  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