2,3-dihydroxypropyl-6-nitro-β-carboline-3-carboxylate | 1026525-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,3-dihydroxypropyl-6-nitro-β-carboline-3-carboxylate
• 英文别名: 2,3-dihydroxypropyl 6-nitro-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1026525-71-2
• 化学式: C₁₅H₁₃N₃O₆
• 分子量: 331.285
• InChiKey: DSCVGJUUSMHLKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-dihydroxypropyl-6-nitro-β-carboline-3-carboxylate 在 盐酸 、 甲酸 、 铁粉 作用下， 反应 0.17h， 以88.5%的产率得到2,3-dihydroxypropyl-6-amino-β-carboline-3-carboxylate dihydrochloride
  参考文献：
  名称：

  β-Carbolines as inverse agonistic benzodiazepine receptor ligands. 2. Synthesis and in vitro and in vivo binding of some new 6-amino- and 6-fluoro-β-carboline-3-carboxylates

  摘要：

  Six new 6-fluoro-beta-carboline-3-carboxylates (3a-f) with their related 6-amino analogues (2a-f) are described and their in vitro and in vivo capabilities to bind to rat cerebral cortex 'benzodiazepine receptors' checked by radioreceptor assay (RRA). For some of the derivatives, the tests were also accomplished in the absence and presence of 10 mu M GABA, whereby an inverse agonistic activity resulted. Their IC50 for [H-3]flunitrazepam displacement were in the 10(-9)-10(-12) molar range. The same compounds, with the exception of the hydroxylated compounds 2e, 2f, 3e and 3f, crossed the blood-brain barrier in the rat, generally giving rise to higher concentrations in the brain (ng/g) than in the plasma(ng/ml). The synthetic pathway preferred here allows a rapid fluorine incorporation in this moiety and an easy isolation of the fluorinated compounds.

  DOI：

  10.1016/0223-5234(96)88232-8
• 作为产物：
  描述：

  methyl 6-nitro-β-carboline-3-carboxylate 在 sodium hydroxide 、 硫酸 作用下， 反应 51.5h， 生成 2,3-dihydroxypropyl-6-nitro-β-carboline-3-carboxylate
  参考文献：
  名称：

  β-Carbolines as inverse agonistic benzodiazepine receptor ligands. 2. Synthesis and in vitro and in vivo binding of some new 6-amino- and 6-fluoro-β-carboline-3-carboxylates

  摘要：

  Six new 6-fluoro-beta-carboline-3-carboxylates (3a-f) with their related 6-amino analogues (2a-f) are described and their in vitro and in vivo capabilities to bind to rat cerebral cortex 'benzodiazepine receptors' checked by radioreceptor assay (RRA). For some of the derivatives, the tests were also accomplished in the absence and presence of 10 mu M GABA, whereby an inverse agonistic activity resulted. Their IC50 for [H-3]flunitrazepam displacement were in the 10(-9)-10(-12) molar range. The same compounds, with the exception of the hydroxylated compounds 2e, 2f, 3e and 3f, crossed the blood-brain barrier in the rat, generally giving rise to higher concentrations in the brain (ng/g) than in the plasma(ng/ml). The synthetic pathway preferred here allows a rapid fluorine incorporation in this moiety and an easy isolation of the fluorinated compounds.

  DOI：

  10.1016/0223-5234(96)88232-8

文献信息

• β-Carbolines as inverse agonistic benzodiazepine receptor ligands. 2. Synthesis and in vitro and in vivo binding of some new 6-amino- and 6-fluoro-β-carboline-3-carboxylates
  作者：G Settimj、MR Del Giudice、R Ferretti、V Cotichini、G Bruni、MR Romeo

  DOI：10.1016/0223-5234(96)88232-8

  日期：1995.1

  Six new 6-fluoro-beta-carboline-3-carboxylates (3a-f) with their related 6-amino analogues (2a-f) are described and their in vitro and in vivo capabilities to bind to rat cerebral cortex 'benzodiazepine receptors' checked by radioreceptor assay (RRA). For some of the derivatives, the tests were also accomplished in the absence and presence of 10 mu M GABA, whereby an inverse agonistic activity resulted. Their IC50 for [H-3]flunitrazepam displacement were in the 10(-9)-10(-12) molar range. The same compounds, with the exception of the hydroxylated compounds 2e, 2f, 3e and 3f, crossed the blood-brain barrier in the rat, generally giving rise to higher concentrations in the brain (ng/g) than in the plasma(ng/ml). The synthetic pathway preferred here allows a rapid fluorine incorporation in this moiety and an easy isolation of the fluorinated compounds.