8,9,10,11-四氢-7H-吡啶并[2,3-a]咔唑 | 64837-03-2

• 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
• 中文名称: 8,9,10,11-四氢-7H-吡啶并[2,3-a]咔唑
• 英文名称: 7,8,9,10-tetrahydro-11H-pyrido[2,3-a]carbazole
• 英文别名: 7,8,9,10-tetrahydropyrido[2,3-a]carbazole；Tetrahydropyrido[2,3-a]carbazole；8,9,10,11-tetrahydro-7H-pyrido[2,3-a]carbazole；8,9,10,11-Tetrahydro-7H-pyrido[2,3-a]carbazol；8,9,10,11-Tetrahydro-7H-pyrido[2,3-a]carbazole
• CAS: 64837-03-2
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: NXHJOIGVGCZYSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8,9,10,11-四氢-7H-吡啶并[2,3-a]咔唑 在 四氯苯醌 、 xylene 作用下， 生成 11H-pyrido[2,3-a]carbazole
  参考文献：
  名称：

  吡啶并咔唑的合成

  摘要：

  7H-吡啶并(2,3-c)- (IX, R=H) 和 7H-吡啶并(3,2-c)咔唑 (V, R=H) 已通过明确的路线合成，并显示与由 Fischer-吲哚闭环产生的产物，然后分别将环己酮的 6-和 7-喹啉腙脱氢。环己酮的 N-取代-1,2,3,4-四氢-6-和-7-喹啉腙环化，然后水解和脱氢产生线性多环系统，6H-吡啶并（3,2-b）-（ VIII) 和 10H-吡啶并(2,3-b)咔唑 (IV)。现在已经制备了12种可能的吡啶并咔唑。1-苯基-5-氨基-1-苯并-三唑(X)的Skraup反应产物的结构已经确定。

  DOI：

  10.1139/v52-084
• 作为产物：
  描述：

  N-(cyclohexylideneamino)quinolin-8-amine 在 PPA 作用下， 反应 1.0h， 以64%的产率得到8,9,10,11-四氢-7H-吡啶并[2,3-a]咔唑
  参考文献：
  名称：

  Preparation and Study of Tautomers Derived from 2-(2‘-Pyridyl)indole and Related Compounds

  摘要：

  Methylation of 2-(2'-pyridyl)indole provides the corresponding N-methylated salt that undergoes deprotonation with mild base to provide the tautomeric (E)-1-methyl-2-(2'-indolenylidene)-1,2-dihydropyridine, whose geometry is established through a NOE experiment. Bridging at the 3,3'-positions leads to tautomers having the opposite stereochemistry. A benzo-fused analogue exhibits similar behavior as does 2-(2'-quinolinyl)pyrrole. The importance of the connectivity to pyridine is examined by considering three possible regioisomers, only two of which show tautomeric behavior. The tautomers show strong solvatochromic dependence and good linear behavior. The indoles absorb at shorter wavelengths and are strongly emitting while the tautomers show a strong bathochromic shift and emit only weakly; the salts exhibit intermediate behavior. NMR properties are consistent with contributions from a dipolar and uncharged resonance form while MO calculations indicate that the indole is about 40 kcal/mol more stable than its tautomer.

  DOI：

  10.1021/jo980134j

文献信息

• Ferlin; Chiarelotto; Marzano, Il Farmaco, 1995, vol. 50, # 2, p. 91 - 98
  作者：Ferlin、Chiarelotto、Marzano、Mobilio、Carlassare、Baccichetti

  DOI：——

  日期：——
• Clemo; Felton, Journal of the Chemical Society, 1951, p. 672,673
  作者：Clemo、Felton

  DOI：——

  日期：——
• 167. Attempts to find new antimalarials. Part XXI
  作者：M. J. S. Dewar

  DOI：10.1039/jr9440000615

  日期：——
• Synthesis and biological properties of a new series of N-pyrido substituted tetrahydrocarbazoles
  作者：M.G. Ferlin、G. Chiarelotto、C. Marzano、E. Severin、F. Baccichetti、F. Carlassare、M. Simonato、F. Bordin

  DOI：10.1016/s0014-827x(98)00048-2

  日期：1998.6

  A series of methyl and ethyl quaternary pyridiniumtetrahydrocarbazoles was synthesized and studied in comparison with ellipticine, chosen as a reference. In general, their antiproliferative activity, tested in different biological substrates, appeared to be higher than that of the corresponding non-quaternarized compounds. This fact could be attributed to the introduction of a positive charge in the molecule, which can stabilize the molecular complex they form with DNA. In a prokaryotic system, the T2 bacteriophage, both quaternarized and non-quaternarized compounds inhibited its infectivity moderately, in a similar way to ellipticine. This effect seemed to be connected to a direct activity on the virions rather than on the indicator bacteria. In mammalian cells, the pyridiniumtetrahydrocarbazoles were more effective. In particular, they appeared to be very active in inhibiting DNA synthesis in Ehrlich ascites cells; some of them were as effective as ellipticine. However, pyridiniumtetrahydrocarbazoles were less active in comparison with ellipticine when their capacity for inhibiting the clonal growth in Chinese hamster ovary (CHO) cells was tested. A similar picture was obtained studying the formation of chromosome aberrations and of sister chromatid exchanges in the same cells. These different responses can be explained considering that the data on DNA synthesis reflect effects only on DNA replication within a short time, without considering any later consequences; on the contrary, in the long-term tests, other events, which lead to cell killing or genotoxicity, can take place. Pyridiniumtetrahydrocarbazoles damage DNA, inducing double-strand breaks efficiently. These observations, together with the data already obtained on unsubstituted derivatives, suggest the pyridiniumtetrahydrocarbazoles induce antiproliferative and genotoxic effects, very probably by inhibiting topoisomerase II. (C) 1998 Elsevier Science S.A. All rights reserved.
• Preparation and Study of Tautomers Derived from 2-(2‘-Pyridyl)indole and Related Compounds
  作者：Feiyue Wu、Jon Hardesty、Randolph P. Thummel

  DOI：10.1021/jo980134j

  日期：1998.6.1

  Methylation of 2-(2'-pyridyl)indole provides the corresponding N-methylated salt that undergoes deprotonation with mild base to provide the tautomeric (E)-1-methyl-2-(2'-indolenylidene)-1,2-dihydropyridine, whose geometry is established through a NOE experiment. Bridging at the 3,3'-positions leads to tautomers having the opposite stereochemistry. A benzo-fused analogue exhibits similar behavior as does 2-(2'-quinolinyl)pyrrole. The importance of the connectivity to pyridine is examined by considering three possible regioisomers, only two of which show tautomeric behavior. The tautomers show strong solvatochromic dependence and good linear behavior. The indoles absorb at shorter wavelengths and are strongly emitting while the tautomers show a strong bathochromic shift and emit only weakly; the salts exhibit intermediate behavior. NMR properties are consistent with contributions from a dipolar and uncharged resonance form while MO calculations indicate that the indole is about 40 kcal/mol more stable than its tautomer.