methyl 6-amino-β-carboline-3-carboxylate dihydrochloride | 107081-74-3

• 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: methyl 6-amino-β-carboline-3-carboxylate dihydrochloride
• 英文别名: 6-amino-3-(methoxycarbonyl)-β-carboline dihydrochloride
• CAS: 107081-74-3
• 化学式: C₁₃H₁₁N₃O₂*2ClH
• 分子量: 314.171
• InChiKey: LNKXQPBZERONDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  81.0
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 6-amino-β-carboline-3-carboxylate dihydrochloride 在 盐酸 、 lithium tetrafluoroborate 、 silica gel 、 sodium nitrite 作用下， 生成 methyl-6-fluoro-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
• 作为产物：
  描述：

  methyl 6-nitro-β-carboline-3-carboxylate 在 palladium on activated charcoal sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以60%的产率得到methyl 6-amino-β-carboline-3-carboxylate dihydrochloride
  参考文献：
  名称：

  β-卡宾灵作为激动剂或拮抗苯并二氮杂receptor受体配体。1。3-甲氧基羰基-β-咔啉（β-CCM）和3-乙氧基羰基-β-咔啉（β-CCE）的一些5、6-和7-氨基衍生物的合成

  摘要：

  将二乙基甲酰基氨基-或二乙基乙酰氨基丙二酸酯与4-，5-或6-硝基葡糖胺1缩合，得到二乙基甲酰基氨基-或二乙基乙酰氨基[（硝基吲哚）-3-基甲基]丙二酸酯2。还原硝基基团，然后将所得氨基化合物3进行N-甲酰化或乙酰化，从而生成4-，5-和6-酰基氨基衍生物4。

  DOI：

  10.1002/jhet.5570250524

文献信息

• Synthesis of 6-substituted .beta.-carbolines that behave as benzodiazepine receptor antagonists or inverse agonists
  作者：Timothy J. Hagen、Phil Skolnick、James M. Cook

  DOI：10.1021/jm00387a033

  日期：1987.4

  The synthesis of the first beta-carboline, 6-(benzylamino)-beta-carboline (1c), to be devoid of a substituent at the 3-position and that still binds to benzodiazepine receptors with potent affinity is described. Furthermore, 1c proved to be a partial inverse agonist when tested in mice. Addition of the benzylamino group at the 6-position of the beta-carboline nucleus is primarily responsible for the activity of beta-carbolines 1b and 1c. The importance of the Nb-nitrogen atom for binding affinity was also demonstrated since 3-(benzylamino)carbazole (6) exhibited little or no affinity for benzodiazepine receptors in vitro, in contrast to the activity of 1c.