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Synthesis of a Cinnamic Acid Derivative and Bioactivity as an Anticancer Based on Result Quantitative Structure Activity Relationship (QSAR) Analysis

Jurnal Akta Kimia Indonesia (Indonesia Chimica Acta) · Vol. ume No. 1 (2020) · pp. 23–29

DOI
10.70561/ica.v13i1.9565
ISSN
2655-6049, 2085-014X
Published
2020-06-24
Publisher
Hasanuddin University
Language
en

Abstract

Synthesis of compound (E)-4-(3-oxo-3-(phenethylamino)prop-1-en-1-il)-1,2-phenylene diacetate (3) analogue (E)-3-(3,4-dihydroxyphenyl)-N-phenethylacrylamide as a recommendation from the QSAR analysis was carried out. The synthesis of these compounds uses the starting material of caffeic acid through the stages of the reaction of acetylation, chlorination, and amidation. Acetylation was carried out using acetic anhydride in pyridine at room temperature for 4 hours. Chlorination was carried out using thionyl chloride reagent in dimethylphromamide solvent under reflux conditions at 80ºC for 4 hours, followed by amidation using phenethylamine in dichloromethane solvent at room temperature for 1 hour. The structure of each phase of the reaction product is identified using FT-IR spectroscopy. Acetylation produces white crystalline solids with melting point 182-184oC, and amidation produces compound 3 in the form of white crystals with melting point 170-173oC. The results of activity tests on murine leukaemia P-388 cells showed that the activity of compound 3 was classified as very strong (IC50 = 0,5 µg /mL) so that it was potentially used as an anticancer drug.

Keywords

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Syahrul AnwarAffiliation unknown1

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Metadata source: OAI-PMH (metadata jurnal) https://journal.unhas.ac.id/index.php/ica/oai, first harvested 5 Nov 2026, last seen 8 Nov 2026.
Original metadata (oai_dc) 
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	<dc:title xml:lang="en">Synthesis of a Cinnamic Acid Derivative and Bioactivity as an Anticancer Based on Result Quantitative Structure Activity Relationship (QSAR) Analysis</dc:title>
	<dc:creator xml:lang="en">Fattah, Abdul</dc:creator>
	<dc:subject xml:lang="en">QSAR</dc:subject>
	<dc:subject xml:lang="en">caffeic acid</dc:subject>
	<dc:subject xml:lang="en">phenethylamino</dc:subject>
	<dc:description xml:lang="en">Synthesis of compound (E)-4-(3-oxo-3-(phenethylamino)prop-1-en-1-il)-1,2-phenylene diacetate (3) analogue (E)-3-(3,4-dihydroxyphenyl)-N-phenethylacrylamide as a recommendation from the QSAR analysis was carried out. The synthesis of these compounds uses the starting material of caffeic acid through the stages of the reaction of acetylation, chlorination, and amidation. Acetylation was carried out using acetic anhydride in pyridine at room temperature for 4 hours. Chlorination was carried out using thionyl chloride reagent in dimethylphromamide solvent under reflux conditions at 80ºC for 4 hours, followed by amidation using phenethylamine in dichloromethane solvent at room temperature for 1 hour. The structure of each phase of the reaction product is identified using FT-IR spectroscopy. Acetylation produces white crystalline solids with melting point 182-184oC, and amidation produces compound 3 in the form of white crystals with melting point 170-173oC. The results of activity tests on murine leukaemia P-388  cells showed that the activity of compound 3 was classified as very strong (IC50 = 0,5 µg /mL) so that it was potentially used as an anticancer drug.</dc:description>
	<dc:publisher xml:lang="en">Hasanuddin University</dc:publisher>
	<dc:date>2020-06-24</dc:date>
	<dc:type>info:eu-repo/semantics/article</dc:type>
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	<dc:type xml:lang="en">Peer-reviewed Article</dc:type>
	<dc:format>application/pdf</dc:format>
	<dc:identifier>https://journal.unhas.ac.id/index.php/ica/article/view/9565</dc:identifier>
	<dc:identifier>10.70561/ica.v13i1.9565</dc:identifier>
	<dc:source xml:lang="en">Jurnal Akta Kimia Indonesia (Indonesia Chimica Acta); Volume 13, No 1: June 2020; 23-29</dc:source>
	<dc:source>2655-6049</dc:source>
	<dc:source>2085-014X</dc:source>
	<dc:language>en</dc:language>
	<dc:relation>https://journal.unhas.ac.id/index.php/ica/article/view/9565/5560</dc:relation>
	<dc:rights xml:lang="en">Copyright (c) 2020 Jurnal Akta Kimia Indonesia (Indonesia Chimica Acta)</dc:rights>
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