(1Z,4E)-1-(4-methoxyphenylamino)-1-(methylthio)-5-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)penta-1, 4-dien-3-one | 1452120-07-8

• 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: (1Z,4E)-1-(4-methoxyphenylamino)-1-(methylthio)-5-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)penta-1, 4-dien-3-one
• CAS: 1452120-07-8
• 化学式: C₂₄H₂₇NO₄S
• 分子量: 425.549
• InChiKey: ROXWTVYYPBGCNU-ZLNJPMDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.79
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  盐酸胍 、 (1Z,4E)-1-(4-methoxyphenylamino)-1-(methylthio)-5-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)penta-1, 4-dien-3-one 以 异丙醇 为溶剂， 反应 24.0h， 以22%的产率得到(E)-N4-(4-methoxyphenyl)-6-(4-((tetrahydro-2H-pyran-2-yl)oxy)styryl)pyrimidine-2,4-diamine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of aryl pyrimidine derivatives as potential leishmanicidal agents

  摘要：

  A series of substituted aryl pyrimidine derivatives was synthesized and evaluated in vitro for their antileishmanial potential against intracellular amastigotes of Leishmania donovani using reporter gene luciferase assay. Among all, 8 compounds showed promising IC50 values ranging from 0.5 to 12.9 mu M. Selectivity indices (S.I.) of all these compounds are far better than reference drugs, sodium stibogluconate (SSG) and miltefosine. On the basis of good S.I., compounds were further screened for their in vivo antileishmanial activity against L. donovani/hamster model. Compounds 2d, 4a and 4b have shown significant inhibition of parasitic multiplication that is 88.4%, 78.1% and 78.2%, respectively at a daily dose of 50 mg/kg x 5 days, when administered intraperitoneally. Compound 2d is most promising one, which may provide a new lead that could be exploited as a new antileishmanial agent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.060
• 作为产物：
  描述：

  (E)-4-(methylthio)-6-(4-(tetrahydro-2H-pyran-2-yloxy)styryl)pyrimidin-2-amine 、 甲氧苯胺 以 乙醇 为溶剂， 反应 24.0h， 以19%的产率得到(1Z,4E)-1-(4-methoxyphenylamino)-1-(methylthio)-5-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)penta-1, 4-dien-3-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of aryl pyrimidine derivatives as potential leishmanicidal agents

  摘要：

  A series of substituted aryl pyrimidine derivatives was synthesized and evaluated in vitro for their antileishmanial potential against intracellular amastigotes of Leishmania donovani using reporter gene luciferase assay. Among all, 8 compounds showed promising IC50 values ranging from 0.5 to 12.9 mu M. Selectivity indices (S.I.) of all these compounds are far better than reference drugs, sodium stibogluconate (SSG) and miltefosine. On the basis of good S.I., compounds were further screened for their in vivo antileishmanial activity against L. donovani/hamster model. Compounds 2d, 4a and 4b have shown significant inhibition of parasitic multiplication that is 88.4%, 78.1% and 78.2%, respectively at a daily dose of 50 mg/kg x 5 days, when administered intraperitoneally. Compound 2d is most promising one, which may provide a new lead that could be exploited as a new antileishmanial agent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.060