3-methoxycarbonyl-1-methyl-6-nitro-β-carboline | 121335-61-3

• 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: 3-methoxycarbonyl-1-methyl-6-nitro-β-carboline
• 英文别名: methyl 1-methyl-6-nitro-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 121335-61-3
• 化学式: C₁₄H₁₁N₃O₄
• 分子量: 285.259
• InChiKey: SILCMMAWEVOWLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  3-methoxycarbonyl-1-methyl-6-nitro-β-carboline 在 sodium tetrahydroborate 、 palladium on activated charcoal 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 6-(3,5-bis(trifluoromethyl)benzamido)-1-methyl-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 1,3,6-trisubstituted β-carboline derivatives for cytotoxic and anti-leishmanial potential

  摘要：

  In the present study, 23 derivatives of 1,3,6-trisubstituted beta-carboline were synthesized and evaluated for cytotoxic potential against four human cancer cells, namely A-549, HeLa, Hep G2 and MCF-7 as well as anti-leishmanial activity against Leishmania donovani (MHOM/80/IN/Dd8) promastigotes. Among the studied compounds, compounds 13c and 13q showed potent cytotoxic activity better than the parent compound 10. For instance, compound 13c was found to be the most cytotoxic with IC50 of 4.72, 3.59, 3.65 and 4.17 mu M against A-549, HeLa, Hep G2 and MCF-7 respectively, while for compound 13q, IC50 were 15.47, 5.30, 6.15 and 13.39 mu M against the same cancer cells respectively. Further, these two compounds were found to be apoptotic in A-549 and MCF-7 cells when observed using Annexin V/propidium iodide staining under confocal microscope. All the compounds were also tested for anti-leishmanial potential. In which, compounds 13u and 13c were found to show moderate inhibition with IC50 of 23.5 +/- 9.0 and 68.0 +/- 0.0 mu M respectively, while compound 10 was the most active with IC50 of 9.0 +/- 2.8 mu M, suggesting the modification at C-6 detrimental for anti-leishmanial activity. Interestingly, amongst all, compound 13c was found to be the most active for cytotoxic and moderately active for anti-leishmanial activity which can be further developed as a lead for these disease areas. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.095
• 作为产物：
  描述：

  DL-色氨酸 在 potassium permanganate 、 氯化亚砜 、 硫酸 、 硝酸 作用下， 以 丙酮 为溶剂， 反应 42.0h， 生成 3-methoxycarbonyl-1-methyl-6-nitro-β-carboline
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 1,3,6-trisubstituted β-carboline derivatives for cytotoxic and anti-leishmanial potential

  摘要：

  In the present study, 23 derivatives of 1,3,6-trisubstituted beta-carboline were synthesized and evaluated for cytotoxic potential against four human cancer cells, namely A-549, HeLa, Hep G2 and MCF-7 as well as anti-leishmanial activity against Leishmania donovani (MHOM/80/IN/Dd8) promastigotes. Among the studied compounds, compounds 13c and 13q showed potent cytotoxic activity better than the parent compound 10. For instance, compound 13c was found to be the most cytotoxic with IC50 of 4.72, 3.59, 3.65 and 4.17 mu M against A-549, HeLa, Hep G2 and MCF-7 respectively, while for compound 13q, IC50 were 15.47, 5.30, 6.15 and 13.39 mu M against the same cancer cells respectively. Further, these two compounds were found to be apoptotic in A-549 and MCF-7 cells when observed using Annexin V/propidium iodide staining under confocal microscope. All the compounds were also tested for anti-leishmanial potential. In which, compounds 13u and 13c were found to show moderate inhibition with IC50 of 23.5 +/- 9.0 and 68.0 +/- 0.0 mu M respectively, while compound 10 was the most active with IC50 of 9.0 +/- 2.8 mu M, suggesting the modification at C-6 detrimental for anti-leishmanial activity. Interestingly, amongst all, compound 13c was found to be the most active for cytotoxic and moderately active for anti-leishmanial activity which can be further developed as a lead for these disease areas. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.095

文献信息

• 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。
• 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：——
• Design, synthesis and biological evaluation of 1,3,6-trisubstituted β-carboline derivatives for cytotoxic and anti-leishmanial potential
  作者：Nitin A. Lunagariya、Vikrantsinh M. Gohil、Varun Kushwah、Soumya Neelagiri、Sanyog Jain、Sushma Singh、Kamlesh K. Bhutani

  DOI：10.1016/j.bmcl.2015.12.095

  日期：2016.2

  In the present study, 23 derivatives of 1,3,6-trisubstituted beta-carboline were synthesized and evaluated for cytotoxic potential against four human cancer cells, namely A-549, HeLa, Hep G2 and MCF-7 as well as anti-leishmanial activity against Leishmania donovani (MHOM/80/IN/Dd8) promastigotes. Among the studied compounds, compounds 13c and 13q showed potent cytotoxic activity better than the parent compound 10. For instance, compound 13c was found to be the most cytotoxic with IC50 of 4.72, 3.59, 3.65 and 4.17 mu M against A-549, HeLa, Hep G2 and MCF-7 respectively, while for compound 13q, IC50 were 15.47, 5.30, 6.15 and 13.39 mu M against the same cancer cells respectively. Further, these two compounds were found to be apoptotic in A-549 and MCF-7 cells when observed using Annexin V/propidium iodide staining under confocal microscope. All the compounds were also tested for anti-leishmanial potential. In which, compounds 13u and 13c were found to show moderate inhibition with IC50 of 23.5 +/- 9.0 and 68.0 +/- 0.0 mu M respectively, while compound 10 was the most active with IC50 of 9.0 +/- 2.8 mu M, suggesting the modification at C-6 detrimental for anti-leishmanial activity. Interestingly, amongst all, compound 13c was found to be the most active for cytotoxic and moderately active for anti-leishmanial activity which can be further developed as a lead for these disease areas. (C) 2015 Elsevier Ltd. All rights reserved.