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Synthesis of cinnamamide derivatives and their α-glucosidase inhibitory activities

Chemically, methyl trans-cinnamate offers treatment at the three main reactive sites such as substitution at the phenyl ring, addition at the α,β-unsaturation, and substitution at the carboxylic methyl ester functionality. We focus our research to the amide and related derivatives of cinnamates beca...

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Main Authors: Teni Ernawati,, Abdul Mun'im,, Muhamad Hanafi,, Yanuar, Arry
Format: Article
Language:English
Published: Penerbit Universiti Kebangsaan Malaysia 2020
Online Access:http://journalarticle.ukm.my/14763/1/ARTIKEL%209.pdf
http://journalarticle.ukm.my/14763/
http://www.ukm.my/jsm/malay_journals/jilid49bil2_2020/KandunganJilid49Bil2_2020.html
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spelling my-ukm.journal.147632020-06-22T08:11:09Z http://journalarticle.ukm.my/14763/ Synthesis of cinnamamide derivatives and their α-glucosidase inhibitory activities Teni Ernawati, Abdul Mun'im, Muhamad Hanafi, Yanuar, Arry Chemically, methyl trans-cinnamate offers treatment at the three main reactive sites such as substitution at the phenyl ring, addition at the α,β-unsaturation, and substitution at the carboxylic methyl ester functionality. We focus our research to the amide and related derivatives of cinnamates because of their lesser known attributes towards antidiabetic activities. In this research, we modify methyl trans-cinnamate by amidating the carboxylic methyl ester functionality using several amines introduced in functional groups of methyl trans-cinnamate. A series of cinnamamide derivatives was synthesized and evaluated for α-glucosidase inhibitory effects. The structure of synthesized compounds was characterized by IR, melting point, UV, 1H NMR, 13C NMR, and mass spectral analysis. All 13 cinnamamide showed higher α-glucosidase activity than the starting compound. The substitution of cinnamic acid with an amide group altered the α-glucosidase inhibitory activity. Increased bulkiness and the chain length of the amine substituents decreased the inhibitory activity. Propylcinnamamide (3c) showed the most potent inhibitory activity among all the cinnamamide derivatives, all of which act through a competitive inhibitory mechanism. These compounds may be worth exploring further. Penerbit Universiti Kebangsaan Malaysia 2020-02 Article PeerReviewed application/pdf en http://journalarticle.ukm.my/14763/1/ARTIKEL%209.pdf Teni Ernawati, and Abdul Mun'im, and Muhamad Hanafi, and Yanuar, Arry (2020) Synthesis of cinnamamide derivatives and their α-glucosidase inhibitory activities. Sains Malaysiana, 49 (2). pp. 315-322. ISSN 0126-6039 http://www.ukm.my/jsm/malay_journals/jilid49bil2_2020/KandunganJilid49Bil2_2020.html
institution Universiti Kebangsaan Malaysia
building Tun Sri Lanang Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Kebangsaan Malaysia
content_source UKM Journal Article Repository
url_provider http://journalarticle.ukm.my/
language English
description Chemically, methyl trans-cinnamate offers treatment at the three main reactive sites such as substitution at the phenyl ring, addition at the α,β-unsaturation, and substitution at the carboxylic methyl ester functionality. We focus our research to the amide and related derivatives of cinnamates because of their lesser known attributes towards antidiabetic activities. In this research, we modify methyl trans-cinnamate by amidating the carboxylic methyl ester functionality using several amines introduced in functional groups of methyl trans-cinnamate. A series of cinnamamide derivatives was synthesized and evaluated for α-glucosidase inhibitory effects. The structure of synthesized compounds was characterized by IR, melting point, UV, 1H NMR, 13C NMR, and mass spectral analysis. All 13 cinnamamide showed higher α-glucosidase activity than the starting compound. The substitution of cinnamic acid with an amide group altered the α-glucosidase inhibitory activity. Increased bulkiness and the chain length of the amine substituents decreased the inhibitory activity. Propylcinnamamide (3c) showed the most potent inhibitory activity among all the cinnamamide derivatives, all of which act through a competitive inhibitory mechanism. These compounds may be worth exploring further.
format Article
author Teni Ernawati,
Abdul Mun'im,
Muhamad Hanafi,
Yanuar, Arry
spellingShingle Teni Ernawati,
Abdul Mun'im,
Muhamad Hanafi,
Yanuar, Arry
Synthesis of cinnamamide derivatives and their α-glucosidase inhibitory activities
author_facet Teni Ernawati,
Abdul Mun'im,
Muhamad Hanafi,
Yanuar, Arry
author_sort Teni Ernawati,
title Synthesis of cinnamamide derivatives and their α-glucosidase inhibitory activities
title_short Synthesis of cinnamamide derivatives and their α-glucosidase inhibitory activities
title_full Synthesis of cinnamamide derivatives and their α-glucosidase inhibitory activities
title_fullStr Synthesis of cinnamamide derivatives and their α-glucosidase inhibitory activities
title_full_unstemmed Synthesis of cinnamamide derivatives and their α-glucosidase inhibitory activities
title_sort synthesis of cinnamamide derivatives and their α-glucosidase inhibitory activities
publisher Penerbit Universiti Kebangsaan Malaysia
publishDate 2020
url http://journalarticle.ukm.my/14763/1/ARTIKEL%209.pdf
http://journalarticle.ukm.my/14763/
http://www.ukm.my/jsm/malay_journals/jilid49bil2_2020/KandunganJilid49Bil2_2020.html
_version_ 1671340601191170048
score 13.211869

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