Sintesis Senyawa 4-(Dimetilamino)calkon Menggunakan Microwave-Assisted Organic Synthesis (MAOS) dengan Variasi Konsentrasi NaOH dan Prediksi Profil Farmakokinetik

Iin Narwanti, Aisyah Khairani Hidayati

Abstract

Senyawa calkon dan turunannya mempunyai aktivitas farmakologi dengan aplikasi yang luas, karenya sintesis senyawa tersebut perlu dipelajari. Oleh karena itu, penelitian ini bertujuan untuk mensintesis 4-(dimetilamino)calkon dari dalam suasana basa dengan metode Microwave-Assisted Organic Synthesis (MAOS) dan memprediksi profil farmakokinetiknya. 4-(dimetilamino)calkon direaksikan dengan asetofenon dengan adanya basa NaOH. Sintesis 4-(dimetilamino)calkon dilakukan dengan iradiasi selama 25 detik dengan daya 140 watt. Variasi konsentrasi katalis NaOH yang digunakan adalah 40%, 50%, dan 60%. Rekristalisasi dilakukan dengan menggunakan pelarut etanol. Produk sintesis dikarakterisasi dengan penentuan titik lebur, KLT, spektrofotometri inframerah, spektrometri massa, 1H-NMR dan 13C-NMR. Selanjutnya, profil farmakokinetik 4-(dimetilamino)calkon diprediksi dengan menggunakan web server SwissADME. Hasil penelitian menunjukkan bahwa rata-rata rendemen sintesis 4-(dimetilamino)calkon dengan metode MAOS pada variasi konsentrasi katalis NaOH 40%, 50%, dan 60% berturut-turut adalah 73,4±1,72%; 90,9±0,68% dan 85,1±1,32%. Konsentrasi NaOH 50% menghasilkan rendemen produk sintesis yang paling optimal. Prediksi sifat fisikokimia dan profil farmakokinetik menggunakan SwissADME menunjukkan bahwa senyawa 4-(dimetilamino)calkon memenuhi aturan Lipinski’s Rule of Five dan mempunyai penyerapan gastrointestinal yang baik dan mampu melewati blood brain barrier (BBB).

Synthesis of 4-(Dimethylamino)chalcone Compound Using Microwave-Assisted Organic Synthesis (MAOS) with Various NaOH Concentration and Pharmacokinetic Profile Prediction. Chalcones and their derivatives are widely established to have a wide application pharmacological activity; therefore, the synthesis is necessary to study. This study aimed to synthesize 4-dimethylaminochalcone in the presence of a base using Microwave-Assisted Organic Synthesis (MAOS) method and predict its pharmacokinetic profile. 4-(dimethylamino)benzaldehyde was treated with acetophenone in the presence of NaOH with various concentrations (40%, 50%, and 60%). Irradiation was conducted for 25 seconds with a power of 140 watts. Recrystallization was carried out from ethanol to give the expected product. The crude product was characterized by melting point determination, TLC, infrared spectrophotometry, mass spectrometry, 1H-NMR, and 13C-NMR. Furthermore, pharmacokinetic profiles of 4-(dimethylamino)chalcone were predicted using the SwissADME web server. The results showed that the average yield of the synthesized product using the MAOS method with catalyst NaOH 40%, 50%, and 60% was 73.4±1.72%, 90.9±0.68%, and 85.1±1.32%, respectively. The optimal yield was obtained using a 50% concentration of NaOH. The pharmacokinetic profiles of 4-(dimethylamino)chalcone analysis using the SwissADME web server showed that 4-(dimethylamino)chalcone complied with Lipinski's Rule of Five. Furthermore, it might have good gastrointestinal absorption and might be able to cross the blood-brain barrier (BBB).

Keywords

4-(dimethylamino) chalcone; Pharmacokinetic; microwave irradiation; MAOS.

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References

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DOI: https://doi.org/10.20961/alchemy.19.2.66542.130-139

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