Synthesis and Anti-Inflammatory Activity of 1-(2,5-Dihydroxyphenyl)-3-Pyridine-2-Yl-Propenone (AEW-1) Compound

Chalcone compounds and some n-hydroxychalcone compounds exhibit anti-inflammatory activity. Chalcone derivatives 1-(2,5-dihydroxyphenyl)-(3-pyridine-2-il)-propenone showed a stronger bond to the COX-2 enzyme than 1-(2,4-dihydroxyphenyl)-3-pyridine-2-il-prophenone, 2′,5′-dihydroxychalcone, 4-chloro-2...

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Autores principales:	Andy Eko Wibowo, Ratna Asmah, Ika Puspitasari
Formato:	article
Lenguaje:	EN
Publicado:	Universitas Gadjah Mada 2021
Materias:	chalcone, n-hydroxychalcone, microwave, k2co3, anti-inflammatory Pharmacy and materia medica RS1-441
Acceso en línea:	https://doaj.org/article/eb774569fa3f42f29570aa558711b039
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spelling	oai:doaj.org-article:eb774569fa3f42f29570aa558711b0392021-11-15T06:08:46ZSynthesis and Anti-Inflammatory Activity of 1-(2,5-Dihydroxyphenyl)-3-Pyridine-2-Yl-Propenone (AEW-1) Compound2338-94272338-948610.22146/ijp.1263https://doaj.org/article/eb774569fa3f42f29570aa558711b0392021-06-01T00:00:00Zhttps://jurnal.ugm.ac.id/v3/IJP/article/view/1263https://doaj.org/toc/2338-9427https://doaj.org/toc/2338-9486Chalcone compounds and some n-hydroxychalcone compounds exhibit anti-inflammatory activity. Chalcone derivatives 1-(2,5-dihydroxyphenyl)-(3-pyridine-2-il)-propenone showed a stronger bond to the COX-2 enzyme than 1-(2,4-dihydroxyphenyl)-3-pyridine-2-il-prophenone, 2′,5′-dihydroxychalcone, 4-chloro-2′, 4′-dihydroxichalcone, and several NSAIDs when they were tested for molecular docking computing using MOE software. It shows that compounds 1-(2,5-dihydroxyphenyl)-(3-pyridine-2-il)-prophenone. Computationally have better anti-inflammatory activity. Synthesis of compounds was by reacting 2,5-dihydroxyacetophenone and pyridincarbaldehyde (without solvent, K2CO3 catalyst) under microwave radiation (radiation strength of P6 / equivalent to 41oC) within 4 minutes. The purification used ethanol washing: aquadest (10:90) and ethanol recrystallization. The structure of the synthesized compound was determined by mass spectroscopy, ultraviolet and visible (UV-Vis), infrared (IR), 1H-NMR, 13C-NMR, DEPT, and 2-dimensional NMR spectroscopy (HMQC, COSY, and HMBC). Anti-inflammatory activity test used rat foot edema method, which was induced by carrageenan. The structural elucidation showed that the compound synthesized was 1-(2,5-dihydroxyphenyl)-(3-pyridine-2-il)-propenone. The compound has a red color, a melting point of 190oC, and a purity of 94% by liquid chromatography. The compound had % DAI (Percentage of Anti-Inflammatory Power) of 50.05 ± 16,244 which was not significantly different from % DAI of ibuprofen (57.22 ± 20.134) (p> 0.05).Andy Eko WibowoRatna AsmahIka PuspitasariUniversitas Gadjah Madaarticlechalcone, n-hydroxychalcone, microwave, k2co3, anti-inflammatoryPharmacy and materia medicaRS1-441ENIndonesian Journal of Pharmacy, Pp 209-220 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	chalcone, n-hydroxychalcone, microwave, k2co3, anti-inflammatory Pharmacy and materia medica RS1-441
spellingShingle	chalcone, n-hydroxychalcone, microwave, k2co3, anti-inflammatory Pharmacy and materia medica RS1-441 Andy Eko Wibowo Ratna Asmah Ika Puspitasari Synthesis and Anti-Inflammatory Activity of 1-(2,5-Dihydroxyphenyl)-3-Pyridine-2-Yl-Propenone (AEW-1) Compound
description	Chalcone compounds and some n-hydroxychalcone compounds exhibit anti-inflammatory activity. Chalcone derivatives 1-(2,5-dihydroxyphenyl)-(3-pyridine-2-il)-propenone showed a stronger bond to the COX-2 enzyme than 1-(2,4-dihydroxyphenyl)-3-pyridine-2-il-prophenone, 2′,5′-dihydroxychalcone, 4-chloro-2′, 4′-dihydroxichalcone, and several NSAIDs when they were tested for molecular docking computing using MOE software. It shows that compounds 1-(2,5-dihydroxyphenyl)-(3-pyridine-2-il)-prophenone. Computationally have better anti-inflammatory activity. Synthesis of compounds was by reacting 2,5-dihydroxyacetophenone and pyridincarbaldehyde (without solvent, K2CO3 catalyst) under microwave radiation (radiation strength of P6 / equivalent to 41oC) within 4 minutes. The purification used ethanol washing: aquadest (10:90) and ethanol recrystallization. The structure of the synthesized compound was determined by mass spectroscopy, ultraviolet and visible (UV-Vis), infrared (IR), 1H-NMR, 13C-NMR, DEPT, and 2-dimensional NMR spectroscopy (HMQC, COSY, and HMBC). Anti-inflammatory activity test used rat foot edema method, which was induced by carrageenan. The structural elucidation showed that the compound synthesized was 1-(2,5-dihydroxyphenyl)-(3-pyridine-2-il)-propenone. The compound has a red color, a melting point of 190oC, and a purity of 94% by liquid chromatography. The compound had % DAI (Percentage of Anti-Inflammatory Power) of 50.05 ± 16,244 which was not significantly different from % DAI of ibuprofen (57.22 ± 20.134) (p> 0.05).
format	article
author	Andy Eko Wibowo Ratna Asmah Ika Puspitasari
author_facet	Andy Eko Wibowo Ratna Asmah Ika Puspitasari
author_sort	Andy Eko Wibowo
title	Synthesis and Anti-Inflammatory Activity of 1-(2,5-Dihydroxyphenyl)-3-Pyridine-2-Yl-Propenone (AEW-1) Compound
title_short	Synthesis and Anti-Inflammatory Activity of 1-(2,5-Dihydroxyphenyl)-3-Pyridine-2-Yl-Propenone (AEW-1) Compound
title_full	Synthesis and Anti-Inflammatory Activity of 1-(2,5-Dihydroxyphenyl)-3-Pyridine-2-Yl-Propenone (AEW-1) Compound
title_fullStr	Synthesis and Anti-Inflammatory Activity of 1-(2,5-Dihydroxyphenyl)-3-Pyridine-2-Yl-Propenone (AEW-1) Compound
title_full_unstemmed	Synthesis and Anti-Inflammatory Activity of 1-(2,5-Dihydroxyphenyl)-3-Pyridine-2-Yl-Propenone (AEW-1) Compound
title_sort	synthesis and anti-inflammatory activity of 1-(2,5-dihydroxyphenyl)-3-pyridine-2-yl-propenone (aew-1) compound
publisher	Universitas Gadjah Mada
publishDate	2021
url	https://doaj.org/article/eb774569fa3f42f29570aa558711b039
work_keys_str_mv	AT andyekowibowo synthesisandantiinflammatoryactivityof125dihydroxyphenyl3pyridine2ylpropenoneaew1compound AT ratnaasmah synthesisandantiinflammatoryactivityof125dihydroxyphenyl3pyridine2ylpropenoneaew1compound AT ikapuspitasari synthesisandantiinflammatoryactivityof125dihydroxyphenyl3pyridine2ylpropenoneaew1compound
_version_	1718428590606909440

Synthesis and Anti-Inflammatory Activity of 1-(2,5-Dihydroxyphenyl)-3-Pyridine-2-Yl-Propenone (AEW-1) Compound

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