methyl 6-nitro-β-carboline-3-carboxylate | 110522-10-6

• 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-nitro-β-carboline-3-carboxylate
• 英文别名: 3-methoxycarbonyl-6-nitro-β-carboline；6-nitro-3-methoxycarbonyl-β-carboline；methyl 6-nitro-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 110522-10-6
• 化学式: C₁₃H₉N₃O₄
• 分子量: 271.232
• InChiKey: WYLNPPZVZSQNCH-UHFFFAOYSA-N

物化性质

• 熔点：
  314-315 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  551.1±45.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-nitro-β-carboline-3-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 6-amino-3-methoxycarbonyl-β-carboline
  参考文献：
  名称：

  Hagen, Timothy J.; Guzman, Filadelfo; Schultz, Christopher, Heterocycles, 1986, vol. 24, # 10, p. 2845 - 2855

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,9-四氢-1H-beta-咔啉-3-甲酸 在 盐酸 、 硝酸 、 sulfur 作用下， 以 xylene 为溶剂， 生成 methyl 6-nitro-β-carboline-3-carboxylate
  参考文献：
  名称：

  Hagen, Timothy J.; Guzman, Filadelfo; Schultz, Christopher, Heterocycles, 1986, vol. 24, # 10, p. 2845 - 2855

  摘要：

  DOI：

文献信息

• Triazine-fused β-carbolines: a facile three-step, one-pot synthesis of novel 2-alkyl(aryl)amino and 2-dialkylamino-7H-[1,3,5]triazino [1',2':1,6]pyrido[3,4-b]indol-4-ones
  作者：Nicolas Primas、Hussein El-Kashef、Jean-Charles Lancelot、Aurélien Lesnard、Robert H. Dodd、Sylvain Rault

  DOI：10.3998/ark.5550190.0011.b14

  日期：——

  A straightforward approach to novel fused β-carbolines namely (1,3,5)triazino (1',2':1,6)pyrido(3,4-b)indol-4-ones is presented. The construction of these compounds was achieved by one-pot synthesis involving condensation of 3-amino-β-carbolines with ethoxycarbonyl isothiocyanate followed by amination of the resulting thioureas and finally thermal ring closure of the resulting guanidines which allowed

  提出了一种新的融合 β-咔啉即 (1,3,5)triazino (1',2':1,6)pyrido(3,4-b)indol-4-ones 的直接方法。这些化合物的构建是通过一锅合成实现的，包括 3-氨基-β-咔啉与乙氧基羰基异硫氰酸酯缩合，然后将所得硫脲胺化，最后使所得胍热闭环，从而获得未报道的标题杂环。
• β-Carbolines as agonistic or antagonistic benzodiazepine receptor ligands.<b>1</b>. Synthesis of some 5-, 6- and 7-amino derivatives of 3-methoxycarbonyl-β-carboline (β-CCM) and of 3-ethoxycarbonyl-β-carboline (β-CCE)
  作者：Guido Settimj、Maria Rosaria Del Giudice、Rosella Ferretti、Franco Gatta

  DOI：10.1002/jhet.5570250524

  日期：1988.9

  Condensation of diethyl formylamino- or diethyl acetylaminomalonate with 4-, 5- or 6-nitrogramine 1 afforded the diethyl formylamino- or the diethyl acetylamino[(nitroindol)-3-ylmethyl]malonates 2; reduction of the nitro group followed by N-formylation or acetylation of the resulting amino compounds 3, led to the 4-, 5-and 6-acylamino derivatives 4.

  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。
• 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.
• SETTIMJ, GUIDO;GIUDICE, MARIA ROSARIA DEL;FERRETTI, ROSELLA;GATTA, FRANCO, J. HETEROCYCL. CHEM., 25,(1988) N, C. 1391-1397
  作者：SETTIMJ, GUIDO、GIUDICE, MARIA ROSARIA DEL、FERRETTI, ROSELLA、GATTA, FRANCO

  DOI：——

  日期：——