3-[4-amino-5-(1-hydroxycyclopropyl)pyrimidin-2-yl]-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: 3-[4-amino-5-(1-hydroxycyclopropyl)pyrimidin-2-yl]-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine
• 英文别名: 1-[4-Amino-2-[1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl]cyclopropan-1-ol
• 化学式: C₂₀H₁₇FN₆O
• 分子量: 376.393
• InChiKey: BMEPMICLQYVFDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(2-氟苄基)-1H-吡唑并[3,4-b]吡啶-3-甲腈 在 三氢化钐 、 氯化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 16.17h， 生成 3-[4-amino-5-(1-hydroxycyclopropyl)pyrimidin-2-yl]-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine
  参考文献：
  名称：

  Metabolites of Orally Active NO-Independent Pyrazolopyridine Stimulators of Soluble Guanylate Cyclase

  摘要：

  The pyrazolopyridine stimulators of soluble guanylate cyclase BAY 41-2272 and 41-8543 were oxidised in rats and dogs at their 5-pyrimidinyl-cyclopropyl and -morpholino residue. These metabolites activate the soluble guanylate cyclase, induce vaso-elaxation and thereby may contribute to the in vivo activity of BAY 41-2272 and BAY 41-8543. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00034-2

文献信息

• A New and Productive Route to 1-Heteroarylcyclopropanols
  作者：Vladimir N. Belov、Andrei I. Savchenko、Viktor V. Sokolov、Alexander Straub、Armin de Meijere

  DOI：10.1002/ejoc.200390093

  日期：2003.2

  hoxyacrylonitrile (4-All) was designed and prepared in five steps (58% overall yield) from ethyl cyclopropylidenacetate as a valuable precursor to various 1-heteroarylcyclopropanols. Its condensation with amidines, guanidine, hydrazine, and methyl thioglycolate and subsequent removal of the allyl protecting group yields 1-heteroarylcyclopropanols such as 1-OH (36% over 2 steps), a very potent NO-independent

  (E/Z)-2-(1-烯丙氧基环丙基)-3-甲氧基丙烯腈 (4-All) 被设计并以五步（58% 总产率）从环丙基乙酸乙酯作为各种 1-杂芳基环丙醇的有价值前体制备。它与脒、胍、肼和巯基乙酸甲酯缩合，随后去除烯丙基保护基，产生 1-杂芳基环丙醇，如 1-OH（2 步 36%），这是一种非常有效的非 NO 依赖性可溶性鸟苷酸环化酶刺激剂。烯丙基醚保护基团的直接裂解 [通过钯催化在 AcOH 中用对甲苯亚磺酸锂取代或用 c-HexMgBr/Ti(OiPr)4 处理] 得到高度官能化的、空间拥挤的 1-杂芳基环丙醇 29、30 和 34完整的氨基和酯基团。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Metabolites of Orally Active NO-Independent Pyrazolopyridine Stimulators of Soluble Guanylate Cyclase
  作者：A Straub

  DOI：10.1016/s0968-0896(02)00034-2

  日期：2002.6

  The pyrazolopyridine stimulators of soluble guanylate cyclase BAY 41-2272 and 41-8543 were oxidised in rats and dogs at their 5-pyrimidinyl-cyclopropyl and -morpholino residue. These metabolites activate the soluble guanylate cyclase, induce vaso-elaxation and thereby may contribute to the in vivo activity of BAY 41-2272 and BAY 41-8543. (C) 2002 Elsevier Science Ltd. All rights reserved.