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A kind of substituted pyrrole derivative and its preparation method and application

A technology of pyrrole derivatives and drugs, applied in organic chemistry, antibacterial drugs, etc., can solve the problems of high requirements, heavy metal residues in drugs, high reaction temperature, etc., and achieve the effect of lowering the temperature and avoiding metal residues

Active Publication Date: 2016-06-29
日照新睿招商发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the alkylation reaction of pyrrole often requires heavy metal catalysts, which will cause heavy metal residues in subsequent drugs; the reaction temperature is high and the requirements are high

Method used

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  • A kind of substituted pyrrole derivative and its preparation method and application
  • A kind of substituted pyrrole derivative and its preparation method and application
  • A kind of substituted pyrrole derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Three-component photochemical reaction of tetracyanobenzene (TCNB), 4-tert-butylstyrene and 1-tert-butoxycarbonyl-pyrrole

[0029] Add 0.530g (3mmol) of tetracyanobenzene, 1.923g (12mmol) of 4-tert-butylstyrene, and 4.013g (24mmol) of 1-Boc-pyrrole into a glass test tube, then add 60ml of acetonitrile to the test tube, and conduct ultrasonic testing. dissolve. Argon was blown for 15 minutes to remove oxygen in the system. Then, it was illuminated for 15 hours under a 500W high-pressure mercury lamp. After the reaction was completed, the reaction mixture was concentrated and the product was separated by silica gel column chromatography, using petroleum ether (b.p.60-90°C)-ethyl acetate as eluent for gradient elution. Compound 1 shown in Formula 3 was obtained with a yield of 45%.

[0030] Compound detection results:

[0031] Melting point: mp200℃; 1 HNMR (CDCl 3 ) δ1H NMR (CDCl3, 400MHz) δ1.31 (s, 9H), 1.56 (s, 9H), 3.43 (dd, 1H, J=15.2, 9.2Hz), 3.72 (dd, 1H, J=14....

Embodiment 2

[0033] Embodiment 2: three-component photochemical reaction of tetracyanobenzene (TCNB), 4-fluorostyrene and N-methylpyrrole

[0034] Add 0.530 g (3 mmol) of tetracyanobenzene, 1.446 g (12 mmol) of 4-fluorostyrene, and 1.497 g (24 mmol) of N-methylpyrrole into a glass test tube, then add 60 ml of acetonitrile into the test tube, and dissolve using ultrasound. Argon was blown for 15 minutes to remove oxygen in the system. Then, it was illuminated for 15 hours under a 500W high-pressure mercury lamp. After the reaction was completed, the reaction mixture was concentrated and the product was separated by silica gel column chromatography, using petroleum ether (b.p.60-90°C)-ethyl acetate as eluent for gradient elution. Compound 2 represented by formula IV was obtained with a yield of 51%.

[0035] Compound detection results:

[0036] Melting point: mp182℃; 1 HNMR (CDCl 3 , 400MHz) δ3.28(dd, 1H, J=16.4, 10.0Hz), 3.40(dd, 1H, J=15.2, 5.6Hz), 3.56(s, 3H), 4.76(dd, 1H, J=9.2, 6....

Embodiment 3

[0038] Embodiment 3: Three-component photochemical reaction of tetracyanobenzene (TCNB), 2,5-dimethylstyrene and N-phenylpyrrole

[0039] Add 0.530g (3mmol) of tetracyanobenzene, 1.586g (12mmol) of 2,5-dimethylstyrene and 1.718g (24mmol) of N-phenylpyrrole into a glass test tube, then add 60ml of acetonitrile to the test tube, and use ultrasonic to dissolve. Argon was blown for 15 minutes to remove oxygen in the system. Then, it was illuminated for 15 hours under a 500W high-pressure mercury lamp. After the reaction was completed, the reaction mixture was concentrated and the product was separated by silica gel column chromatography, using petroleum ether (b.p.60-90°C)-ethyl acetate as eluent for gradient elution. Compound 3 represented by formula V was obtained with a yield of 80%.

[0040] The detection results of compound 3:

[0041] Melting point: mp176-177℃; 1 HNMR (CDCl 3 , 400MHz) δ2.00(s, 3H), 2.31(s, 3H), 3.22(dd, 1H, J=15.2, 10.8Hz), 3.42(dd, 1H, J=15.2, 4.8Hz)...

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PUM

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Abstract

The invention provides a substituted pyrrole derivative and pharmaceutically acceptable salts thereof, also provides a preparation method of the above mentioned compound and application thereof to preparation of antibacterial drugs. The invention does not use expensive metal catalyst, thereby avoiding the problem of trace metal residue in drug synthesis; light reaction can be carried out under the condition of room temperature, so as to lower reaction temperature; and through the introduction of other active groups in the pyrrole ring, novel pyrrole derivative with antibacterial activity is obtained.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a substituted pyrrole derivative, in particular to a preparation method for synthesizing a substituted pyrrole derivative through a light-induced three-component reaction. Background technique [0002] Many natural products contain structural units of substituted pyrrole rings, and these compounds generally have strong physiological activities such as antibacterial, antitumor and anti-HIV. For example, patent CN1882568A discloses a series of pyrrole derivatives with antibacterial activity. [0003] Due to the high electron-richness of pyrrole and its sensitivity to acid and oxygen, the alkylation reaction of pyrrole and other electron-rich nitrogen-containing heterocycles is still a relatively difficult subject. Conventional Friedel-Crafts alkylation reactions are not suitable for pyrroles because the Or Lewis strong acidic conditions will cause non-regioselective polyalkylatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/337A61P31/04
CPCC07D207/337
Inventor 沈永淼唐剑肖慧泉邵颖尚小东陶菲菲
Owner 日照新睿招商发展有限公司