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Coumarin[4,3-b] pyrrole derivative as well as synthesis method and application thereof

A synthetic method and coumarin technology, applied in the direction of drug combination, medical preparations containing active ingredients, pharmaceutical formulas, etc., can solve the problems of complex processing, long reaction time, unfriendly environment, etc., and achieve mild reaction conditions and after-treatment Easy handling and environmentally friendly effects

Inactive Publication Date: 2021-11-26
LINYI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the synthesis method reported above, there are the following problems: need to use expensive noble metal catalysts, such as palladium, silver, etc., and need to use protonic acid as the reaction solvent; the reaction raw materials are not easy to obtain, and multi-step synthesis is required; the applicability of the reaction substrate is limited , the reaction yield is not high; the reaction needs to be carried out at high temperature; the reaction time is too long, it takes up to 72 hours; the post-reaction treatment is relatively complicated and unfriendly to the environment
More importantly, these methods are difficult to directly introduce 3,3-disubstituent-2-propanonyl at the 2-position of coumarino[4,3-b]pyrrole

Method used

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  • Coumarin[4,3-b] pyrrole derivative as well as synthesis method and application thereof
  • Coumarin[4,3-b] pyrrole derivative as well as synthesis method and application thereof
  • Coumarin[4,3-b] pyrrole derivative as well as synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of 1-phenyl-2-(3,3-diphenyl-2-acetonyl)coumarino[4,3-b]pyrrole(IA)

[0030]

[0031] Under air, 0.3 mmol of 4-anilinocoumarin, 0.36 mmol of furyl alcohol, 3 mL of 1,2-dichloroethane, and 0.09 mmol of aluminum trichloride were added to a sealed 10 mL tube. React at 80°C for 2 hours, then cool to room temperature to obtain the target product formula (IA), an orange solid, with an isolated yield of 85%. MP 176-178°C.

[0032] Product NMR data: 1H NMR (CDCl 3 ,400MHz): δ3.74(s,1H),5.00(s,1H),6.43(dd,J 1 =8.0Hz,J 2 =1.2Hz,1H),6.78(s,1H),6.54(t,J=7.6Hz,1H),7.03-7.05(m,4H),7.23-7.28(m,9H),7.36(dd,J 1 =8.4Hz,J 2 =0.8Hz, 1H), 7.51(t, J=8.0Hz, 2H), 7.62(t, J=7.6Hz, 1H); 13C NMR (CDCl 3 ,100MHz): δ40.34,63.21,108.08,109.90,113.95,117.74,120.56,123.41,127.35,128.22,128.75,130.12,130.18,132.80,135.65,1357.02,1152.60,9.9

[0033] High resolution mass spectrometry data: HRMS(ESI,m / z)calcd.for C 32 h 24 NO 3 [M+H] +calc.: 470.1751; found: 470.1736.

Embodiment 2

[0035] Synthesis of 1-phenyl-2-(3,3-diphenyl-2-propanonyl)-8-methylcoumarino[4,3-b]pyrrole (IB)

[0036]

[0037] Under air, 0.3 mmol of 6-methyl-4-anilinocoumarin, 0.45 mmol of furyl alcohol, 3 mL of 1,2-dichloroethane, and 0.09 mmol of aluminum trichloride were added to a sealed 10 ml tube under air. React at 80°C for 2 hours, then cool to room temperature to obtain the target product formula (IB), a yellow solid, with an isolated yield of 80%. MP 170-172°C.

[0038] Product NMR data: 1H NMR (CDCl 3 ,400MHz):δ2.02(s,3H),3.74(s,2H),5.02(s,1H),6.14(s,1H),6.77(s,1H),7.03-7.07(m,5H), 7.23-7.28 (m, 9H), 7.50-7.53 (m, 2H), 7.61-7.64 (m, 1H); 13C NMR (CDCl 3 ,100MHz):δ21.00,40.37,63.20,108.06,109.89,113.57,117.41,120.74,127.36,128.76,128.80,128.84,129.13,130.00,130.08,132.58,132.78,135.78,137.13,137.64,150.24,159.23, 203.42.

[0039] High resolution mass spectrometry data: HRMS(ESI,m / z)calcd.for C 33 h 26 NO 3 [M+H]+calc.: 484.1907; found: 484.1895.

Embodiment 3

[0041] Synthesis of 1-phenyl-2-(3,3-diphenyl-2-acetonyl)-7-methoxycoumarino[4,3-b]pyrrole (IC)

[0042]

[0043] Under air, 0.3 mmol of 7-methoxy-4-anilinocoumarin, 0.45 mmol of furyl alcohol, 3 mL of 1,2-dichloroethane, and 0.09 mmol of aluminum trichloride were added to a sealed 10 ml tube under air. React at 80°C for 2 hours, then cool to room temperature to obtain the target product formula (IC), a yellow solid, with an isolated yield of 75%. MP 189-192°C.

[0044] Product NMR data: 1H NMR (CDCl 3 ,400MHz):δ3.71(s,2H),3.76(s,3H),5.00(s,1H),6.31(d,J=7.2Hz,1H),6.44(dd,J 1 =7.2Hz,J 2 =2.4Hz,1H),6.74(s,1H),6.87(d,J=2.4Hz,1H),7.03-7.05(m,4H),7.23-7.27(m,8H),7.48-7.51(m, 2H), 7.58-7.62 (m, 1H); 13CNMR (CDCl 3 ,100MHz):δ40.35,55.44,63.11,101.94,107.31,107.79,107.91,111.21,121.47,127.31,128.72,128.77,128.80,130.08,131.85,136.45,137.03,137.65,153.67,159.20,159.77,203.50。

[0045] High resolution mass spectrometry data: HRMS(ESI,m / z)calcd.for C 33 h 26 NO 4 [M+H]+calc.: ...

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Abstract

The invention discloses a coumarin[4,3-b] pyrrole derivative and a synthesis method thereof. According to the method, a 4-amino coumarin compound and a furanol compound are adopted as raw materials, an organic solvent and a catalyst are added for catalytic synthesis to obtain the coumarin[4,3-b] pyrrole derivative as shown in a formula (I). The preparation method does not need precious metal catalysis and is environment-friendly. The invention further discloses application of the coumarin[4,3-b] pyrrole derivative shown in the formula (I) in preparation of antibacterial, anti-tumor, anti-oxidation, anti-HIV or anticoagulant drugs.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and specifically relates to a coumarino[4,3-b]pyrrole derivative and its synthesis method and application Background technique [0002] Coumarino[4,3-b]pyrrole derivatives are an important class of organic compounds. They are the core skeleton of many natural products and drug molecules. They have antifungal, antiviral, anti-inflammatory, anti-tumor, anti-HIV, Wide range of pharmacological effects such as anticoagulation and antioxidation, these pharmacological effects are partly attributed to the planar structure modification of coumarinopyrrole. In addition, coumarino[4,3-b]pyrrole derivatives can also be used in the field of functional materials such as fluorescent probes, and the pyrrole ring can be used as an intermediate in organic synthesis to facilitate further derivatization. Therefore, the development of synthetic methods for such compounds has important practical significance...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052A61K31/407A61P7/02A61P35/00A61P31/18A61P39/06A61P31/00
CPCC07D491/052A61P7/02A61P35/00A61P31/18A61P39/06A61P31/00
Inventor 王程宇管鹏程韩玉孔令凯
Owner LINYI UNIVERSITY