Synthesis, biological screening, and in silico physicochemical analysis of novel 1,2,3-triazolyl oleate esters
Herein, oleic acid was derivatized to 1,2,3-triazolyl oleate esters through propargylation followed by copper(I)-mediated azide-alkyne [3 + 2] cycloaddition, confirmed by IR, NMR and HRMS. All products exhibited similar antioxidant activity to oleic acid. The products demonstrated antibacterial acti...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-12-01
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| Series: | Case Studies in Chemical and Environmental Engineering |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666016424004080 |
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| author | Hilna Diana Sahaya Bayu Ardiansah Sumi Hudiyono Erwahyuni Endang Prabandari Titin Ariyani Tuti Wukirsari Hiroki Tanimoto Antonius Herry Cahyana |
| author_facet | Hilna Diana Sahaya Bayu Ardiansah Sumi Hudiyono Erwahyuni Endang Prabandari Titin Ariyani Tuti Wukirsari Hiroki Tanimoto Antonius Herry Cahyana |
| author_sort | Hilna Diana Sahaya |
| collection | DOAJ |
| description | Herein, oleic acid was derivatized to 1,2,3-triazolyl oleate esters through propargylation followed by copper(I)-mediated azide-alkyne [3 + 2] cycloaddition, confirmed by IR, NMR and HRMS. All products exhibited similar antioxidant activity to oleic acid. The products demonstrated antibacterial activity at 10 mg/mL. Compound 4d was identified as the most potent cytotoxic agent, showing 34.31 % inhibition at 200 μM against the MCF-7. Additionally, 4d displayed 15.85 % inhibition of shikimate kinase at 0.5 mg/mL. Thus, these modified compounds exhibit better activity compared to oleic acid, making this series a promising candidate for drug discovery and development. |
| format | Article |
| id | doaj-art-d358241c00fa4d77a9e7949966cdfba6 |
| institution | Kabale University |
| issn | 2666-0164 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Case Studies in Chemical and Environmental Engineering |
| spelling | doaj-art-d358241c00fa4d77a9e7949966cdfba62024-12-02T05:06:33ZengElsevierCase Studies in Chemical and Environmental Engineering2666-01642024-12-0110101014Synthesis, biological screening, and in silico physicochemical analysis of novel 1,2,3-triazolyl oleate estersHilna Diana Sahaya0Bayu Ardiansah1Sumi Hudiyono2Erwahyuni Endang Prabandari3Titin Ariyani4Tuti Wukirsari5Hiroki Tanimoto6Antonius Herry Cahyana7Department of Chemistry, Faculty of Mathematics and Natural Sciences (FMIPA), Universitas Indonesia, 16424, Depok, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences (FMIPA), Universitas Indonesia, 16424, Depok, Indonesia; Corresponding author.Department of Chemistry, Faculty of Mathematics and Natural Sciences (FMIPA), Universitas Indonesia, 16424, Depok, IndonesiaResearch Center for Vaccine and Drugs, National Research and Innovation Agency (BRIN), KST Soekarno, Jalan Raya Bogor KM 46, 16911, Bogor, West Java, IndonesiaResearch Center for Vaccine and Drugs, National Research and Innovation Agency (BRIN), KST Soekarno, Jalan Raya Bogor KM 46, 16911, Bogor, West Java, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences (FMIPA), Universitas Indonesia, 16424, Depok, IndonesiaFaculty of Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama, 930-0194, JapanDepartment of Chemistry, Faculty of Mathematics and Natural Sciences (FMIPA), Universitas Indonesia, 16424, Depok, IndonesiaHerein, oleic acid was derivatized to 1,2,3-triazolyl oleate esters through propargylation followed by copper(I)-mediated azide-alkyne [3 + 2] cycloaddition, confirmed by IR, NMR and HRMS. All products exhibited similar antioxidant activity to oleic acid. The products demonstrated antibacterial activity at 10 mg/mL. Compound 4d was identified as the most potent cytotoxic agent, showing 34.31 % inhibition at 200 μM against the MCF-7. Additionally, 4d displayed 15.85 % inhibition of shikimate kinase at 0.5 mg/mL. Thus, these modified compounds exhibit better activity compared to oleic acid, making this series a promising candidate for drug discovery and development.http://www.sciencedirect.com/science/article/pii/S2666016424004080Oleic acid1,2,3-TriazoleHybrid compoundBiological screening |
| spellingShingle | Hilna Diana Sahaya Bayu Ardiansah Sumi Hudiyono Erwahyuni Endang Prabandari Titin Ariyani Tuti Wukirsari Hiroki Tanimoto Antonius Herry Cahyana Synthesis, biological screening, and in silico physicochemical analysis of novel 1,2,3-triazolyl oleate esters Case Studies in Chemical and Environmental Engineering Oleic acid 1,2,3-Triazole Hybrid compound Biological screening |
| title | Synthesis, biological screening, and in silico physicochemical analysis of novel 1,2,3-triazolyl oleate esters |
| title_full | Synthesis, biological screening, and in silico physicochemical analysis of novel 1,2,3-triazolyl oleate esters |
| title_fullStr | Synthesis, biological screening, and in silico physicochemical analysis of novel 1,2,3-triazolyl oleate esters |
| title_full_unstemmed | Synthesis, biological screening, and in silico physicochemical analysis of novel 1,2,3-triazolyl oleate esters |
| title_short | Synthesis, biological screening, and in silico physicochemical analysis of novel 1,2,3-triazolyl oleate esters |
| title_sort | synthesis biological screening and in silico physicochemical analysis of novel 1 2 3 triazolyl oleate esters |
| topic | Oleic acid 1,2,3-Triazole Hybrid compound Biological screening |
| url | http://www.sciencedirect.com/science/article/pii/S2666016424004080 |
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