Isatin (1H-indole-2,3-dione) merupakan senyawa heterosiklik yang memiliki bioaktivitas beragam. Senyawa spiro merupakan senyawa bisiklik yang terikat dengan satu atom yang sama dan memiliki bioaktivitas sebagai antioksidan. Pada penelitian ini, dilakukan sintesis senyawa turunan spiro[indol-azetidinon] berbasis isatin dan 5-kloroisatin yang diharapkan memiliki aktivitas antioksidan. Senyawa turunan spiro[indol-azetidinon] disintesis dari isatin dan 5-kloroisatin dengan variasi amina aromatik primer membentuk senyawa intermediet basa Schiff yang direaksikan dengan asam kloroasetat dan trietilamina dengan kehadiran katalis nanopartikel K2CO3. Nanopartikel K2CO3 disintesis dari K2CO3 anhidrat dengan etanol dan asam laurat yang dikarakterisasi menggunakan XRD, BET, dan SEM. Didapatkan nanopartikel K2CO3 memiliki ukuran kristal rata-rata sebesar 31,49 nm. Senyawa turunan spiro[indol-azetidinon] diidentifikasi menggunakan KLT serta dikarakterisasi menggunakan FTIR, UV-Vis, dan LC-MS. Didapatkan senyawa basa Schiff 1, 2, 3, dan 4 dengan persen yield masing-masing sebesar 18,21%, 10,06%, 21,13%, dan 7,39%. Didapatkan persen yield dari senyawa turunan spiro[indol-azetidinon] 1, 2, 3, dan 4 masing-masing sebesar 20,46%, 16,77%, 62,87%, dan 45,56%. Hasil uji aktivitas antioksidan dengan metode DPPH menunjukkan nilai IC50 untuk senyawa turunan spiro[indol-azetidinon] 1, 2, 3, dan 4 masing-masing sebesar 503,34 ppm, 586,52 ppm, 763,15 ppm, dan 933,22 ppm.
Isatin (1H-indole-2,3-dione) is heterocyclic compound which has various bioactivities. Spiro compounds are bicyclic compounds that bound to the same atom and have bioactivity as antioxidants. In this research, synthesis of spiro[indole-azetidinone] derivatives based on isatin and 5-chloroisatin was carried out that expected to have antioxidant activity. Spiro[indole-azetidinone] derivatives were synthesized from isatin and 5-chloroisatin with a variety of primary aromatic amines formed Schiff base intermediate compounds that reacted with chloroacetic acid and triethylamine in the presence of K2CO3 nanoparticles catalyst. K2CO3 nanoparticles were synthesized from anhydrous K2CO3 with ethanol and lauric acid that characterized using XRD, BET, and SEM. It was found that K2CO3 nanoparticles had an average crystal size of 31.49 nm. Spiro[indole-azetidinone] derivatives were identified using TLC and characterized using FTIR, UV-Vis, and LC-MS. The Schiff base compounds 1, 2, 3, and 4 were obtained with yield percents of 18.21%, 10.06%, 21.13%, and 7.39%, respectively. The percent yield of spiro[indole-azetidinone] 1, 2, 3, and 4 derivatives were 20.46%, 16.77%, 62.87%, and 45.56%, respectively. The results of antioxidant activity tests using DPPH method showed the IC50 values ââfor spiro[indole-azetidinone] 1, 2, 3, and 4 derivatives were 503.34 ppm, 586.52 ppm, 763.15 ppm, and 933.22 ppm, respectively. |
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