ethyl 3-[ethoxycarbonyl-[2-[(2R)-oxolan-2-yl]ethyl]amino]-5-(1-methylpyrazol-4-yl)furo[2,3-b]pyridine-2-carboxylate | 1431433-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 3-[ethoxycarbonyl-[2-[(2R)-oxolan-2-yl]ethyl]amino]-5-(1-methylpyrazol-4-yl)furo[2,3-b]pyridine-2-carboxylate
• CAS: 1431433-88-3
• 化学式: C₂₃H₂₈N₄O₆
• 分子量: 456.499
• InChiKey: RHZPHBCAMRFLFX-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-氟-5-溴吡啶 、 ethyl 3-[ethoxycarbonyl-[2-[(2R)-oxolan-2-yl]ethyl]amino]-5-(1-methylpyrazol-4-yl)furo[2,3-b]pyridine-2-carboxylate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到ethyl N-[2-(6-fluoropyridine-3-carbonyl)-5-(1-methylpyrazol-4-yl)furo[2,3-b]pyridin-3-yl]-N-[2-[(2R)-oxolan-2-yl]ethyl]carbamate
  参考文献：
  名称：

  Nucleotide competing reverse transcriptase inhibitors: Discovery of a series of non-basic benzofurano[3,2-d]pyrimidin-2-one derived inhibitors

  摘要：

  A HTS screen led to the identification of a benzofurano[3,2-d]pyrimidin-2-one core structure which upon further optimization resulted in 1 as a potent HIV-1 nucleotide competing reverse transcriptase inhibitor (NcRTI). Investigation of the SAR at N-1 allowed significant improvements in potency and when combined with the incorporation of heterocycles at C-8 resulted in potent analogues not requiring a basic amine to achieve antiviral activity. Additional modifications at N-1 resulted in 33 which demonstrated excellent antiviral potency and improved physicochemical properties. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.02.021
• 作为产物：
  描述：

  (R)-四氢呋喃甲酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 水 、 silver benzoate 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 ethyl 3-[ethoxycarbonyl-[2-[(2R)-oxolan-2-yl]ethyl]amino]-5-(1-methylpyrazol-4-yl)furo[2,3-b]pyridine-2-carboxylate
  参考文献：
  名称：

  Nucleotide competing reverse transcriptase inhibitors: Discovery of a series of non-basic benzofurano[3,2-d]pyrimidin-2-one derived inhibitors

  摘要：

  A HTS screen led to the identification of a benzofurano[3,2-d]pyrimidin-2-one core structure which upon further optimization resulted in 1 as a potent HIV-1 nucleotide competing reverse transcriptase inhibitor (NcRTI). Investigation of the SAR at N-1 allowed significant improvements in potency and when combined with the incorporation of heterocycles at C-8 resulted in potent analogues not requiring a basic amine to achieve antiviral activity. Additional modifications at N-1 resulted in 33 which demonstrated excellent antiviral potency and improved physicochemical properties. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.02.021

文献信息

• Nucleotide competing reverse transcriptase inhibitors: Discovery of a series of non-basic benzofurano[3,2-d]pyrimidin-2-one derived inhibitors
  作者：Clint A. James、Patrick DeRoy、Martin Duplessis、Paul J. Edwards、Teddy Halmos、Joannie Minville、Louis Morency、Sébastien Morin、Bruno Simoneau、Martin Tremblay、Richard Bethell、Michael Cordingley、Jianmin Duan、Louie Lamorte、Alex Pelletier、Daniel Rajotte、Patrick Salois、Sonia Tremblay、Claudio F. Sturino

  DOI：10.1016/j.bmcl.2013.02.021

  日期：2013.5

  A HTS screen led to the identification of a benzofurano[3,2-d]pyrimidin-2-one core structure which upon further optimization resulted in 1 as a potent HIV-1 nucleotide competing reverse transcriptase inhibitor (NcRTI). Investigation of the SAR at N-1 allowed significant improvements in potency and when combined with the incorporation of heterocycles at C-8 resulted in potent analogues not requiring a basic amine to achieve antiviral activity. Additional modifications at N-1 resulted in 33 which demonstrated excellent antiviral potency and improved physicochemical properties. (C) 2013 Published by Elsevier Ltd.