6-hydroxy-1,3-dimethyl-5-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 6-hydroxy-1,3-dimethyl-5-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
• 英文别名: 6-hydroxy-1,3-dimethyl-5-(2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one；6-hydroxy-1,3-dimethyl-2-sulfanylidene-5-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)pyrimidin-4-one
• 化学式: C₁₇H₁₈N₄O₂S
• 分子量: 342.422
• InChiKey: YLYASIIZEVKKDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,9-二氢-3H-吡啶并(3,4-B)吲哚 、 1,3-二甲基-2-硫代巴比妥酸 以 various solvent(s) 为溶剂， 反应 1.0h， 以94%的产率得到6-hydroxy-1,3-dimethyl-5-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
  参考文献：
  名称：

  摘要：

  Addition of N-substituted barbituric and 2-thiobarbituric acids to 3,4-dihydro-beta-carboline results in formation of N-alkyl-6-hydroxy-5-(2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)-1H-pyrimidine-2,4-diones and their 2-thioanalogs, which are structural analogs of alkaloids from annomontin group. Acylation of 1,3-dimethyl-substituted adduct is accompanied by opening of the tetrahydropyridine ring furnishing N-{2-[2-(1,3-dimethyl-2,4,6-trioxotetrahydropyrimidin-5-ylidenomethyl)-1H-indol-3-yl] ethyl} acetamide. The structure of compounds synthesized was studied by means of H-1 NMR spectroscopy.

  DOI：

  10.1023/a:1026028405999

文献信息

• ——
  作者：K. A. Krasnov、V. G. Kartsev、M. N. Yurova

  DOI：10.1023/a:1026028405999

  日期：——

  Addition of N-substituted barbituric and 2-thiobarbituric acids to 3,4-dihydro-beta-carboline results in formation of N-alkyl-6-hydroxy-5-(2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)-1H-pyrimidine-2,4-diones and their 2-thioanalogs, which are structural analogs of alkaloids from annomontin group. Acylation of 1,3-dimethyl-substituted adduct is accompanied by opening of the tetrahydropyridine ring furnishing N-2-[2-(1,3-dimethyl-2,4,6-trioxotetrahydropyrimidin-5-ylidenomethyl)-1H-indol-3-yl] ethyl} acetamide. The structure of compounds synthesized was studied by means of H-1 NMR spectroscopy.