1-(3-ethyl-7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-8-yl)-3-(4-chlorophenyl)urea | 1592003-42-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 1-(3-ethyl-7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-8-yl)-3-(4-chlorophenyl)urea
• CAS: 1592003-42-3
• 化学式: C₁₉H₁₇ClN₂O₄
• 分子量: 372.808
• InChiKey: JTCWIAKRGLNVHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  91.57
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  草酰氯 、 1-(3-ethyl-7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-8-yl)-3-(4-chlorophenyl)urea 以 苯 为溶剂， 以89%的产率得到3-(4-chlorophenyl)-1-(3-ethyl-7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-8-yl)imidazolidin-2,4,5-trione
  参考文献：
  名称：

  Synthesis, docking and in vitro anticancer evaluation of some new benzopyrone derivatives

  摘要：

  The synthesis of some new 3-alkyl-7-hydroxy-4-methyl-8-substituted-1H-benzopyran-2-ones, 6-alkyl-7-methyl-2-substituted amino-5H-pyrano[6,5-e] benzoxazol-5-ones, 7-alkyl-8-methyl-3-substituted-2,6-dihydropyrano[6,5-f]-1,4-benzoxazin-6-ones, 7,8-disubstituted-3-ethyl-4-methyl-1H-benzopyran-2-ones and 3-alkyl-4-methyl-7-substituted-1H-benzopyran-2-ones were described. Fourteen compounds were selected by National Cancer Institute (NCI), Bethesda, and evaluated for their in vitro anticancer activity in the full NCI 60 cell lines panel assay by a single dose test. Compounds 4a, 18a, 18b and 23a were found to be broad-spectrum antitumors showing effectiveness toward numerous cell lines that belong to different tumor subpanels. Furthermore, docking studies were undertaken to gain insight into the possible binding mode of these compounds with the binding site of the casein kinase II (CK2) enzyme which is involved in cell survival and proliferation through a number of downstream effectors. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.02.003
• 作为产物：
  描述：

  3-乙基-7-羟基-4-甲基-2H-色烯-2-酮 在 ammonium hydroxide 、 sodium dithionite 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 7.25h， 生成 1-(3-ethyl-7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-8-yl)-3-(4-chlorophenyl)urea
  参考文献：
  名称：

  Synthesis, docking and in vitro anticancer evaluation of some new benzopyrone derivatives

  摘要：

  The synthesis of some new 3-alkyl-7-hydroxy-4-methyl-8-substituted-1H-benzopyran-2-ones, 6-alkyl-7-methyl-2-substituted amino-5H-pyrano[6,5-e] benzoxazol-5-ones, 7-alkyl-8-methyl-3-substituted-2,6-dihydropyrano[6,5-f]-1,4-benzoxazin-6-ones, 7,8-disubstituted-3-ethyl-4-methyl-1H-benzopyran-2-ones and 3-alkyl-4-methyl-7-substituted-1H-benzopyran-2-ones were described. Fourteen compounds were selected by National Cancer Institute (NCI), Bethesda, and evaluated for their in vitro anticancer activity in the full NCI 60 cell lines panel assay by a single dose test. Compounds 4a, 18a, 18b and 23a were found to be broad-spectrum antitumors showing effectiveness toward numerous cell lines that belong to different tumor subpanels. Furthermore, docking studies were undertaken to gain insight into the possible binding mode of these compounds with the binding site of the casein kinase II (CK2) enzyme which is involved in cell survival and proliferation through a number of downstream effectors. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.02.003