Indonesian Journal of Chemistry
Vol 22, No 6 (2022)

Synthesis of N-phenethyl-p-methoxycinnamamide and N-morpholinyl-p-methoxycinnamamide, In Vitro and In Silico Study as α-Glucosidase Inhibitor

Herlina Rasyid (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Hasanuddin University, Jl. Perintis Kemerdekaan km 10, Makassar 90245, South Sulawesi, Indonesia)
Firdaus Firdaus (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Hasanuddin University, Jl. Perintis Kemerdekaan km 10, Makassar 90245, South Sulawesi, Indonesia)
Syadza Firdausiah (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Hasanuddin University, Jl. Perintis Kemerdekaan km 10, Makassar 90245, South Sulawesi, Indonesia)
Nunuk Hariani Soekamto (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Hasanuddin University, Jl. Perintis Kemerdekaan km 10, Makassar 90245, South Sulawesi, Indonesia)
Seniwati Seniwati (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Hasanuddin University, Jl. Perintis Kemerdekaan km 10, Makassar 90245, South Sulawesi, Indonesia)
Riska Mardiyanti (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Hasanuddin University, Jl. Perintis Kemerdekaan km 10, Makassar 90245, South Sulawesi, Indonesia)
Reynaldi Reynaldi (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Hasanuddin University, Jl. Perintis Kemerdekaan km 10, Makassar 90245, South Sulawesi, Indonesia)
Andi Eka Sri Rahayu (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Hasanuddin University, Jl. Perintis Kemerdekaan km 10, Makassar 90245, South Sulawesi, Indonesia)
Wahyu Dita Saputri (Research Center for Quantum Physics, National Research and Innovation Agency (BRIN), Habibie Science and Technology Complex (Puspiptek), Serpong 15314, South Tangerang, Indonesia)



Article Info

Publish Date
03 Nov 2022

Abstract

Aromatic ginger (Kaempferia galanga L.) is one of the natural sources containing ethyl-p-methoxycinnamate, which is known to have beneficial activity, especially as an α-glucosidase inhibitor. This study aims to convert ethyl-p-methoxycinnamate into amide form as N-phenethyl-p-methoxycinnamamide (4a) and N-morpholinyl-p-methoxycinnamamide (4b) through some synthetic ways then tested their activity as an α-glucosidase inhibitor. The FTIR spectra of 4a present a short single peak at 3269.34 cm−1 that belongs to the N-H group, while spectra of 4b show no absorption band between 3200–3400 cm−1 due to its tertiary amide structure. Spectroscopy analysis through 1H- and 13C-NMR exhibits the successful synthesis of both compounds. Bioactivity test results show that compound 4b has better activity than 4a. In molecular dynamics simulation, the binding energy of compounds 4a and 4b reveal that both compounds have a similar binding energy of about -98980.8 and -97696.7 kJ mol−1, respectively.

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Journal Info

Abbrev

ijc

Publisher

Subject

Chemical Engineering, Chemistry & Bioengineering Chemistry

Description

Indonesian Journal of Chemistry is an International, peer-reviewed, open access journal that publishes original research articles, review articles, as well as short communication in all areas of chemistry including applied chemistry. The journal is accredited by The Ministry of Research, Technology ...