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Polycyclic quinoline derivatives and their preparation and application

A polycyclic quinoline and derivative technology, applied in the field of polycyclic quinoline derivatives and their preparation and application, can solve the problems of step economy and atom economy inefficiency, and achieve high yield and cheap and easy-to-obtain raw materials , simple and mild effect

Active Publication Date: 2022-07-19
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 derivatives and their preparation and application
  • Polycyclic quinoline derivatives and their preparation and application
  • Polycyclic quinoline derivatives and their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Synthesis of compound represented by (III-1)

[0045] Weigh 0.225mmol tryptamine isocyanide (compound corresponding to No. (1), 0.0383g), 0.15mmol C,N iminoisoquinoline dipole (compound corresponding to No. (12), 0.0450g) in a 20mL test tube In the reaction tube, add 3 mL of methanol as a solvent, and stir the reaction at 25°C for 24 hours; after the reaction, the reaction solution is subjected to vacuum evaporation and column chromatography separation (column chromatography separation conditions: the stationary phase is 200-300 mesh silica gel powder, flowing The phases were ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A:B) was 1:6) to obtain 0.0382 g of the reaction product.

[0046] The above reaction products were characterized, and the results were:

[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....

Embodiment 2

[0049] Example 2: Synthesis of compound represented by (III-2)

[0050] Weigh 0.225mmol of 5-methyltryptamine isonitrile (compound corresponding to No. (2), 0.0414g), 0.15mmol C,N iminoisoquinoline dipole (compound corresponding to No. (12), 0.0450g) In a 20mL test tube reaction tube, add 3mL methanol as a solvent, and stir the reaction at 25°C for 24 hours; after the reaction, the reaction solution is subjected to vacuum evaporation and column chromatography separation (column chromatography separation conditions: the stationary phase is 200-300 mesh Silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A:B) is 1:6) to obtain 0.0344 g of reaction product.

[0051] The above reaction products were characterized, and the results were:

[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 (...

Embodiment 3

[0054] Example 3: Synthesis of compound represented by (III-3)

[0055] Weigh 0.225mmol of 6-methyltryptamine isonitrile (compound corresponding to No. (3), 0.0414g), 0.15mmol C,N iminoisoquinoline dipole (compound corresponding to No. (12), 0.0450g) In a 20mL test tube reaction tube, add 3mL methanol as a solvent, and stir the reaction at 25°C for 24 hours; after the reaction, the reaction solution is subjected to vacuum evaporation and column chromatography separation (column chromatography separation conditions: the stationary phase is 200-300 mesh Silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A:B) is 1:6) to obtain 0.0305g of reaction product.

[0056] The above reaction products were characterized, and the results were:

[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....

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Abstract

The present invention relates to a polycyclic quinoline derivative and its preparation and application. The structure of the polycyclic quinoline derivative is shown in formula (III): wherein, R 1 selected from hydrogen, C 1 ‑C 5 Alkyl, halogen, C 6 ‑C 10 Aryl, C 1 ‑C 5 alkoxy; R 2 selected from hydrogen, C 1 ‑C 5 Alkyl, C 1 ‑C 5 Alkoxycarbonyl; R 3 selected from hydrogen, C 1 ‑C 5 Alkyl; base is selected from phenyl, substituted phenyl, naphthyl, pyrrolyl or thienyl, and the substituent on substituted phenyl is selected from C 1 ‑C 5 Alkyl, phenyl or halogen. The polycyclic quinoline derivative of the present invention is constructed in one step using simple raw materials, has mild reaction conditions, is environmentally friendly, and is simple to operate, and the polycyclic quinoline derivative has tumor suppressing 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 are widely found in natural products and biologically active molecules. For example, suadimins A is a Chinese herbal medicine extract with antibacterial effects; communesins A is isolated from Penicillium spp. Obtained, has certain cytotoxicity; (-)-communesins F has insecticidal and anti-malignant cell proliferation efficacy (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 efficien...

Claims

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Application Information

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Patent Type & Authority Patents(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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