An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity

Ethyl p-methoxycinnamate (EPMC) (1) is a major natural ester found in the rhizome of Kaempferia galanga and has been reported to have anti-inflammatory activity. Some of the structural modification of this compound has been carried out in order to study the structure-activity relationship on its ant...

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Autores principales:	Ismiarni Komala, Supandi Supandi, Ahmad Thantow, Andrianopsyah Mas Jaya Putra
Formato:	article
Lenguaje:	EN
Publicado:	Universitas Gadjah Mada 2020
Materias:	anti-inflammatory direct amidation n,n-dimethyl-p-methoxycinnamamide ethyl p-methoxycinnamate kaempferia galanga microwave-promoted synthesis Pharmacy and materia medica RS1-441
Acceso en línea:	https://doaj.org/article/541d0511f20a4b47abea1021c33e7599
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spelling	oai:doaj.org-article:541d0511f20a4b47abea1021c33e75992021-11-15T06:08:47ZAn Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity2338-94272338-948610.22146/ijp.812https://doaj.org/article/541d0511f20a4b47abea1021c33e75992020-09-01T00:00:00Zhttps://jurnal.ugm.ac.id/v3/IJP/article/view/812https://doaj.org/toc/2338-9427https://doaj.org/toc/2338-9486Ethyl p-methoxycinnamate (EPMC) (1) is a major natural ester found in the rhizome of Kaempferia galanga and has been reported to have anti-inflammatory activity. Some of the structural modification of this compound has been carried out in order to study the structure-activity relationship on its anti-inflammatory activity. In the present study, we report a new, simple and efficient procedure in the conversion of the ethyl p-methoxycinnamate into N,N-dimethyl-p-methoxycinnamamide (5) and then study the structure-activity relationship on its anti-inflammatory activity. The reaction was carried out through a microwave-assisted direct amidation between (EPMC) (1) with dimethylformamide (DMF) in the basic condition. The mixture was irradiated by using unmodified microwave-oven at 300 W for 1 minute to obtain compound (5) in 88.8% yields. The extensive analysis of the GCMS and NMR data supported that the product of synthesis is N,N-dimethyl-p-methoxycinnamamide (5). Evaluation of the anti-inflammatory activity of compound 5 by using anti-denaturation of heat bovine serum albumin (BSA) assay indicated that N,N-dimethyl-p-methoxycinnamamide (5) still have anti-denaturation activity. Compound 5 has an amide functional group which is more slowly hydrolyzed if compared to 1. Hence, the reaction has successfully produced a more stable compound which still has anti-inflammatory activityIsmiarni KomalaSupandi SupandiAhmad ThantowAndrianopsyah Mas Jaya PutraUniversitas Gadjah Madaarticleanti-inflammatorydirect amidationn,n-dimethyl-p-methoxycinnamamideethyl p-methoxycinnamatekaempferia galangamicrowave-promoted synthesisPharmacy and materia medicaRS1-441ENIndonesian Journal of Pharmacy, Pp 144-149 (2020)
institution	DOAJ
collection	DOAJ
language	EN
topic	anti-inflammatory direct amidation n,n-dimethyl-p-methoxycinnamamide ethyl p-methoxycinnamate kaempferia galanga microwave-promoted synthesis Pharmacy and materia medica RS1-441
spellingShingle	anti-inflammatory direct amidation n,n-dimethyl-p-methoxycinnamamide ethyl p-methoxycinnamate kaempferia galanga microwave-promoted synthesis Pharmacy and materia medica RS1-441 Ismiarni Komala Supandi Supandi Ahmad Thantow Andrianopsyah Mas Jaya Putra An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity
description	Ethyl p-methoxycinnamate (EPMC) (1) is a major natural ester found in the rhizome of Kaempferia galanga and has been reported to have anti-inflammatory activity. Some of the structural modification of this compound has been carried out in order to study the structure-activity relationship on its anti-inflammatory activity. In the present study, we report a new, simple and efficient procedure in the conversion of the ethyl p-methoxycinnamate into N,N-dimethyl-p-methoxycinnamamide (5) and then study the structure-activity relationship on its anti-inflammatory activity. The reaction was carried out through a microwave-assisted direct amidation between (EPMC) (1) with dimethylformamide (DMF) in the basic condition. The mixture was irradiated by using unmodified microwave-oven at 300 W for 1 minute to obtain compound (5) in 88.8% yields. The extensive analysis of the GCMS and NMR data supported that the product of synthesis is N,N-dimethyl-p-methoxycinnamamide (5). Evaluation of the anti-inflammatory activity of compound 5 by using anti-denaturation of heat bovine serum albumin (BSA) assay indicated that N,N-dimethyl-p-methoxycinnamamide (5) still have anti-denaturation activity. Compound 5 has an amide functional group which is more slowly hydrolyzed if compared to 1. Hence, the reaction has successfully produced a more stable compound which still has anti-inflammatory activity
format	article
author	Ismiarni Komala Supandi Supandi Ahmad Thantow Andrianopsyah Mas Jaya Putra
author_facet	Ismiarni Komala Supandi Supandi Ahmad Thantow Andrianopsyah Mas Jaya Putra
author_sort	Ismiarni Komala
title	An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity
title_short	An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity
title_full	An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity
title_fullStr	An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity
title_full_unstemmed	An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity
title_sort	efficient directly conversion of the ethyl p-methoxycinnamate into n,n-dimethyl-p-methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity
publisher	Universitas Gadjah Mada
publishDate	2020
url	https://doaj.org/article/541d0511f20a4b47abea1021c33e7599
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An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity

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