Ethyl 2-cyano-3-(4-propan-2-yloxyphenyl)prop-2-enoate | 773089-54-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Ethyl 2-cyano-3-(4-propan-2-yloxyphenyl)prop-2-enoate
• CAS: 773089-54-6
• 化学式: C₁₅H₁₇NO₃
• mdl: MFCD06210302
• 分子量: 259.305
• InChiKey: ISISXFVYWJPXST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,3-二氟苄基)-异硫脲氢溴酸盐 、 Ethyl 2-cyano-3-(4-propan-2-yloxyphenyl)prop-2-enoate 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 生成 2-(2,3-difluorobenzylsulfanyl)-4-hydroxy-6-(4-isopropoxy-phenyl)-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  The discovery of potent, orally bioavailable pyrimidine-5-carbonitrile-6-alkyl CXCR2 receptor antagonists

  摘要：

  A hit-to-lead optimisation programme was carried out on the Novartis archive screening hit, pyrimidine 2-((2,6-dichlorobenzyl)thio)-5-isocyano-6-phenylpyrimidin-4-ol 4, resulting in the discovery of CXCR2 receptor antagonist 24(2,3-difluorobenzyl)thio)-6-(2-(hydroxymethyl)cyclopropyl)-5-isocyanopyrimidin-4-ol 24. The SAR was investigated by systematic variation of the aromatic group at c-6, the linker between c-2 and the halogenated ring, and the c-5 nitrile moiety. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.011
• 作为产物：
  描述：

  氰乙酸乙酯 、 4-异丙氧基苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 Ethyl 2-cyano-3-(4-propan-2-yloxyphenyl)prop-2-enoate
  参考文献：
  名称：

  The discovery of potent, orally bioavailable pyrimidine-5-carbonitrile-6-alkyl CXCR2 receptor antagonists

  摘要：

  A hit-to-lead optimisation programme was carried out on the Novartis archive screening hit, pyrimidine 2-((2,6-dichlorobenzyl)thio)-5-isocyano-6-phenylpyrimidin-4-ol 4, resulting in the discovery of CXCR2 receptor antagonist 24(2,3-difluorobenzyl)thio)-6-(2-(hydroxymethyl)cyclopropyl)-5-isocyanopyrimidin-4-ol 24. The SAR was investigated by systematic variation of the aromatic group at c-6, the linker between c-2 and the halogenated ring, and the c-5 nitrile moiety. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.011

文献信息

• The discovery of potent, orally bioavailable pyrimidine-5-carbonitrile-6-alkyl CXCR2 receptor antagonists
  作者：David W. Porter、Michelle Bradley、Zarin Brown、Steven J. Charlton、Brian Cox、Peter Hunt、Diana Janus、Sarah Lewis、Paul Oakley、Des O’Connor、John Reilly、Nichola Smith、Neil J. Press

  DOI：10.1016/j.bmcl.2014.06.011

  日期：2014.8

  A hit-to-lead optimisation programme was carried out on the Novartis archive screening hit, pyrimidine 2-((2,6-dichlorobenzyl)thio)-5-isocyano-6-phenylpyrimidin-4-ol 4, resulting in the discovery of CXCR2 receptor antagonist 24(2,3-difluorobenzyl)thio)-6-(2-(hydroxymethyl)cyclopropyl)-5-isocyanopyrimidin-4-ol 24. The SAR was investigated by systematic variation of the aromatic group at c-6, the linker between c-2 and the halogenated ring, and the c-5 nitrile moiety. (C) 2014 Elsevier Ltd. All rights reserved.