Ethyl 3-[2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]ethyl]-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate | 257635-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: Ethyl 3-[2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]ethyl]-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate
• CAS: 257635-54-4
• 化学式: C₂₁H₃₀N₄O₄
• 分子量: 402.494
• InChiKey: PUOWCSSFFIXENT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 3-[2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]ethyl]-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate 在 lithium hydroxide 、 sodium hydroxide 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  1,2,4-Triazolo[3,4-a]pyridine as a novel, constrained template for fibrinogen receptor (GPIIb/IIIa) antagonists

  摘要：

  Conformationally constrained analogues of the GPIIb/IIIa antagonist elarofiban (RWJ-53308) have been synthesized and biologically evaluated. The 1,2,4-triazolo[3,4-a]pyridine scaffold provided potent antagonists with favorable pharmacodynamic and pharmacokinetic attributes in dogs. Compounds 12a and 13a exhibited enhancements in oral bioavailability, t(1/2), and ex vivo duration of action (inhibition of ADP-induced platelet aggregation) relative to elarofiban. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00529-7
• 作为产物：
  描述：

  2-氯烟酸乙酯 在 N-甲基吗啉 、 4 A molecular sieve 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 肼 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 41.0h， 生成 Ethyl 3-[2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]ethyl]-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate
  参考文献：
  名称：

  Synthesis of triazolopyridines as conformationally constrained tertiary amides

  摘要：

  Amide derivatives of cyclic amines are common templates for biologically active chemical entities. To constrain the tertiary amide moiety of N-acylpiperidine-based GPIIb/IIIa antagonists for further structure-activity study, we have prepared new 1,2,4-triazolo[4,3-a]pyridines. The syntheses of two classes of triazolopyridines are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00632-8

文献信息

• 1,2,4-Triazolo[3,4-a]pyridine as a novel, constrained template for fibrinogen receptor (GPIIb/IIIa) antagonists
  作者：Edward C Lawson、William J Hoekstra、Michael F Addo、Patricia Andrade-Gordon、Bruce P Damiano、Jack A Kauffman、John A Mitchell、Bruce E Maryanoff

  DOI：10.1016/s0960-894x(01)00529-7

  日期：2001.10

  Conformationally constrained analogues of the GPIIb/IIIa antagonist elarofiban (RWJ-53308) have been synthesized and biologically evaluated. The 1,2,4-triazolo[3,4-a]pyridine scaffold provided potent antagonists with favorable pharmacodynamic and pharmacokinetic attributes in dogs. Compounds 12a and 13a exhibited enhancements in oral bioavailability, t(1/2), and ex vivo duration of action (inhibition of ADP-induced platelet aggregation) relative to elarofiban. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of triazolopyridines as conformationally constrained tertiary amides
  作者：Edward C. Lawson、Bruce E. Maryanoff、William J. Hoekstra

  DOI：10.1016/s0040-4039(00)00632-8

  日期：2000.6

  Amide derivatives of cyclic amines are common templates for biologically active chemical entities. To constrain the tertiary amide moiety of N-acylpiperidine-based GPIIb/IIIa antagonists for further structure-activity study, we have prepared new 1,2,4-triazolo[4,3-a]pyridines. The syntheses of two classes of triazolopyridines are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.