2-benzamido-3-(6-hydroxynaphthalen-2-yl)propanoic acid | 1334953-02-4

• 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: 2-benzamido-3-(6-hydroxynaphthalen-2-yl)propanoic acid
• CAS: 1334953-02-4
• 化学式: C₂₀H₁₇NO₄
• 分子量: 335.359
• InChiKey: SPOXXRUAHCDYBX-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：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzamido-3-(6-hydroxynaphthalen-2-yl)propanoic acid 、 4-氯氯苄 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以73%的产率得到(+/-)-3-(2-(4-chlorobenzyloxy)naphthalen-6-yl)-2-(benzamido)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：

  2-benzamido-3-(6-(benzoyloxy)naphthalen-2-yl)propanoic acid 在 lithium hydroxide monohydrate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 8.0h， 以75%的产率得到2-benzamido-3-(6-hydroxynaphthalen-2-yl)propanoic acid
  参考文献：
  名称：

  设计，合成和评估新型2-氨基-3-（萘-2-基）丙酸衍生物作为血小板聚集的有效抑制剂

  摘要：

  基于先前确定的抗血小板凝集剂LX2421，设计，合成和评估了一系列新型的2-氨基-3-（萘-2-基）丙酸衍生物。其中，化合物LX14和LX25被鉴定为有前途的抗血小板凝集剂。的体外生物研究表明，LX14可以阻止血小板聚集在与比较抑制GPIIb / IIIa受体诱导四个不同的诱导剂，并显示可比较的效力替罗非班。此外，LX14的出血风险比替罗非班低得多，并且在体内显示出显着的抗血栓形成活性。综上所述，结果表明LX14是一种有前途的针对血小板凝集的GPIIb / IIIa受体拮抗剂，值得进一步评估。

  DOI：

  10.1016/j.ejmech.2016.09.032

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.
• Design, synthesis and evaluation of novel 2-amino-3-(naphth-2-yl)propanoic acid derivatives as potent inhibitors of platelet aggregation
  作者：Zhouling Xie、Benimana Oscar、Lulu Zhao、Xue Ding、Chen Cao、Sen Feng、Han Li、Chen Pan、Ziyi Bian、Yang Li、Weijun Wang、Yi Kong、Zhiyu Li

  DOI：10.1016/j.ejmech.2016.09.032

  日期：2017.1

  antiplatelet aggregation agent, a series of novel 2-amino-3-(naphth-2-yl)propanoic acid derivatives were designed, synthesized and evaluated. Among them, compounds LX14 and LX25 were identified as promising antiplatelet aggregation agents. The in vitro biologic study demonstrated that LX14 can block platelet aggregation induced by four different inducers and displays comparable potency in inhibiting GPIIb/IIIa

  基于先前确定的抗血小板凝集剂LX2421，设计，合成和评估了一系列新型的2-氨基-3-（萘-2-基）丙酸衍生物。其中，化合物LX14和LX25被鉴定为有前途的抗血小板凝集剂。的体外生物研究表明，LX14可以阻止血小板聚集在与比较抑制GPIIb / IIIa受体诱导四个不同的诱导剂，并显示可比较的效力替罗非班。此外，LX14的出血风险比替罗非班低得多，并且在体内显示出显着的抗血栓形成活性。综上所述，结果表明LX14是一种有前途的针对血小板凝集的GPIIb / IIIa受体拮抗剂，值得进一步评估。