Muhammad Ilham Royyan Nafi’, - (2021) Studi Molecular Docking Dan Sintesis Senyawa 4-Formil-2-Metoksifenil 4-Metilbenzoat Sebagai Jalur Sintesis Asam 4-(4-Metil)Benzoiloksi-3-Metoksisinamat Dengan Iradiasi Gelombang Mikro. Skripsi thesis, UNIVERSITAS AIRLANGGA.

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Abstract

Background In 2016, 16% of the causes of death worldwide were cancer. While in Indonesia 12% of the causes of death are cancer. Ferulic acid has radical-scavenging activity, which protects cells from free radicals thereby reducing the risk of cancer. Modification of the OH group on ferulic acid with acyl halide p-methyl benzoyl chloride can increase its antiproliferative activity because it has a more stable ligand-receptor bond. Objective: This study aims to determine the inhibit COX-2 effect of 4-(4-methyl)benzoyloxy-3-methoxycinnamic acid and the synthesis of vanillin with p-methyl benzoyl chloride through a nucleophilic acyl substitution reaction that produces 4-formyl-2-methoxyphenyl 4-methylbenzoate. Methods: Ferulic acid and 4-(4-methyl)benzoyloxy-3-methoxycinnamic acid were found for their MolDock Score at the COX-2 receptor in-silico using the Molegro Virtual Docker application. Synthesis of 4-formyl-2-methoxyphenyl 4-methylbenzoate was carried out by microwave at 20W, 40W, and 400W power. Results 4-(4-methyl)benzoyloxy-3-methoxycinnamic acid had a lower MDS than ferulic acid at the COX-2 receptor. The synthesis of 4-formyl-2-methoxyphenyl 4-methylbenzoate at a power of 40W for 10 x 30 seconds did not get a perfect reaction and at a power of 400W for 7 x 30 seconds it has resulted in a degraded compound. At 200W power for 10 x 30 seconds, the reaction ran perfectly with the vanillin being used up which resulted in yield percentage 78.06 ± 6.39%. Conclusion: By in-silico test, 4-(4-methyl)benzoyloxy-3-methoxycinnamic acid was able to inhibit COX-2 better than ferulic acid. 4-formyl-2-methoxyphenyl 4-methylbenzoate can be synthesized from vanillin and p-methylbenzoyl chloride. The synthesis of 4-formyl-2-methoxyphenyl 4-methylbenzoate is affected by the power of the microwave.

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