Polycyclic quinoline derivative as well as preparation and application thereof

A technology for polycyclic quinolines and derivatives, applied in the fields of polycyclic quinoline derivatives and their preparation and application, capable of solving the problems of step economy and low efficiency of atom economy, achieving high yield and high atom economy , The effect of cheap and easy-to-obtain raw materials

Active Publication Date: 2021-12-28
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although there have been several reports on the effective synthesis of such compounds, these methods all require traditional total synthesis, which is very inefficient in terms of step economy and atom economy.

Method used

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  • Polycyclic quinoline derivative as well as preparation and application thereof
  • Polycyclic quinoline derivative as well as preparation and application thereof
  • Polycyclic quinoline derivative as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the compound shown in synthetic (III-1)

[0045] Weigh 0.225mmol tryptamine isocyanide (compound corresponding to number (1), 0.0383g), 0.15mmol C, N imine isoquinoline dipole (compound corresponding to number (12), 0.0450g) in a 20mL test tube In the reaction tube, add 3mL of methanol as a solvent, and stir and react at 25°C for 24 hours; The phases were ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B) was 1:6), and 0.0382 g of the reaction product was obtained.

[0046] The above-mentioned reaction product is characterized, and the result is:

[0047] 1 H NMR (400MHz, DMSO- d6 )δ=7.59–7.47(m,3H),7.42–7.24(m,5H),7.00(s,1H),3.82–3.74(m,1H),3.55–3.46(m,1H),3.10–2.95( m,2H),2.76–2.62(m,3H),1.73(td,J=11.6,6.6Hz,1H),one H was overlapped with solvent peak 2.54–2.44;

[0048] According to the characterization data, it can be seen that the obtained reaction product is a pure product (purity>95%); the product yield is calculated,...

Embodiment 2

[0049] Embodiment 2: the compound shown in synthetic (III-2)

[0050] Weigh 0.225mmol 5-methyltryptamine isonitrile (compound corresponding to number (2), 0.0414g), 0.15mmol C, N imine isoquinoline dipole (compound corresponding to number (12), 0.0450g) In a 20mL test tube reaction tube, add 3mL of methanol as a solvent, and stir at 25°C for 24 hours; Silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B) is 1:6), and 0.0344g of the reaction product is obtained.

[0051] The above-mentioned reaction product is characterized, and the result is:

[0052] 1 H NMR (400MHz, DMSO- d6 )δ=7.52(dd,J=7.4,1.2Hz,1H),7.41–7.33(m,3H),7.32–7.24(m,2H),7.14(dd,J=7.9,1.2Hz,1H),6.97 (s,1H),3.84–3.71(m,1H),3.55–3.42(m,1H),3.12–2.93(m,2H),2.78–2.68(m,1H),2.68–2.58(m,2H) ,2.36(s,3H),1.71(td,J=11.6,6.8Hz,1H),one H was overlapped with solvent peak 2.53–2.43;

[0053] According to the characterization data, it can be seen that the ...

Embodiment 3

[0054] Embodiment 3: the compound shown in synthetic (III-3)

[0055] Weigh 0.225mmol 6-methyltryptamine isonitrile (compound corresponding to number (3), 0.0414g), 0.15mmol C, N imine isoquinoline dipole (compound corresponding to number (12), 0.0450g) In a 20mL test tube reaction tube, add 3mL of methanol as a solvent, and stir at 25°C for 24 hours; Silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B) is 1:6), and 0.0305g of the reaction product is obtained.

[0056] The above-mentioned reaction product is characterized, and the result is:

[0057] 1 H NMR (400MHz, CDCl 3 )δ=7.65(dd,J=7.3,1.4Hz,1H),7.49(s,1H),7.38–7.29(m,2H),7.23–7.13(m,3H),6.78(s,1H),3.88 –3.80(m,1H),3.68–3.60(m,1H),3.29–3.18(m,1H),3.15–3.05(m,1H),2.88–2.74(m,2H),2.66–2.57(m, 1H), 2.38(s, 3H), 2.02–1.92(m, 1H), 1.74(s, 1H);

[0058] According to the characterization data, it can be seen that the obtained reaction product is a pure prod...

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Abstract

The invention relates to a polycyclic quinoline derivative as well as preparation and application thereof. The structure of the polycyclic quinoline derivative is shown as a formula (III), wherein R1 is selected from hydrogen, C1-C5 alkyl, halogen, C6-C10 aryl and C1-C5 alkoxy; R2 is selected from hydrogen, alkyl with 1 to 5 carbon atoms and alkoxycarbonyl with 1 to 5 carbon atoms; R3 is selected from hydrogen and C1-C5 alkyl; and the Ar, shown as the specification, is selected from phenyl, substituted phenyl, naphthyl, pyrrolyl or thienyl, and a substituent group on the substituted phenyl is selected from C1-C5 alkyl, phenyl or halogen. The polycyclic quinoline derivative disclosed by the invention is constructed by utilizing simple raw materials in one step, is mild in reaction condition, environment-friendly and simple to operate, and has tumor inhibition activity.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a polycyclic quinoline derivative and its preparation and application. Background technique [0002] Polycyclic quinoline derivatives are a class of nitrogen-containing heterocyclic compounds with important biological activities, which widely exist in natural products and bioactive molecules. For example, suadimins A is an extract of Chinese herbal medicine, which has antibacterial effects; communesins A is isolated from Penicillium (-)-communesins F has insecticidal and anti-malignant cell proliferation effects (Tetrahedron Lett.1993,34,2355; J.Org.Chem.2002,67,7124; Tetrahedron2008,64, 1397; Org. Lett. 2019, 21, 4554; Org. Lett. 2019, 21, 7065.). Therefore, the construction of quinoline alkaloids has attracted extensive research interest in recent years. [0003] [0004] Although there have been several reports on the effective synthesis of such compounds, these methods a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22C07D495/22A61K31/55A61P35/00
CPCC07D471/22C07D495/22A61P35/00
Inventor 纪顺俊曹文斌徐小平
Owner SUZHOU UNIV
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