Microwave-assisted synthesis of 1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one and its activities as an antioxidant, sunscreen, and antibacterial

Abstract

Chalcone analogs have been reported to have a variety of exciting biological activities, such as anticancer, anti-inflammatory, antioxidant, photoprotective, antibacterial, and antidiabetic activities. Therefore, analogs of these compounds have been widely synthesized as intermediate compounds or target molecules in the discovery of bioactive compounds to be applied in the pharmaceutical field. The purpose of this study is to synthesize chalcone analog compounds (E)-1-(4-hydroxyphenyl)-3-(4-methoxyphenyl) prop-2-en-1-on with the microwave irradiation method and explore some of the biological activities of these compounds, including testing the antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method, in vitro sunscreen activity by microplate method, and antibacterial activity by disk diffusion method. DPPH test results indicate that the compound has weak antioxidant activity, with an IC50 value of 300.43 µg/mL. However, the compound showed excellent potential as a UV B and UV A filter at a concentration of 150 µg/mL with a value of %Te of 0.73±0.10% (sunblock), %Tp of 0.07±0.00% (sunblock), SPF value of 21.10±1.46 (ultra-protection) and potentially better than benzophenone-3 as a standard sunscreen. Then, disk diffusion testing showed that the compound had weak antibacterial activity against Staphylococcus aureus and did not show antibacterial activity against Escherichia coli bacteria at test concentrations of 30, 60, and 120 µg/disk.

(E)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3c] Pyridine

“…The antioxidant activity evaluation for the title compound was performed by following the previously reported literatures [18][19][20] with slight modification. First, 10 mg of the title compound were dissolved in 10 mL methanol (1000 µg/mL).…”

“…Then, as much as 80 µL of DPPH solution (40 µg/mL) were transferred to lines A-G, while line H was just filled with 130 µL of methanol as a blank and the test solutions were incubated for 30 min at room temperature in the dark room. The absorbance was measured at a wavelength of 517 nm with a 96-well microplate reader and the percentage of DPPH inhibition was calculated using formulae from previous reports [18][19][20]. The IC 50 value was calculated based on the linear regression equation (y = ax + b) from the curve by plotting the Ln concentration and the percentage of inhibition (see Supplementary Materials, Table S2 and Figure S34).…”

“…The IC 50 value was calculated based on the linear regression equation (y = ax + b) from the curve by plotting the Ln concentration and the percentage of inhibition (see Supplementary Materials, Table S2 and Figure S34). Then, the IC 50 value was categorized based on the previous reports [18][19][20].…”

Uji Aktivitas Antibakteri Senyawa 4 Dimetilaminokalkon Terhadap Bakteri Staphylococcus Aureus Dan Escherichia Coli Atcc

“…Pengamatan zona hambat bakteri dilakukan setelah 24 jam masa inkubasi dan zona hambat diukur menggunakan jangka sorong. Aktivitas penghambatan senyawa kalkon terhadap bakteri dinyatakan dengan kekuatan penghambatan yang yang merujuk pada rumus dibawah ini: (Ikhtiarudin et al, 2020) ISSN : 2774-5848 (Online) ISSN : 2774-0524 (Cetak) Diameter zona hambat sampel Kemampuan penghambatan (%) =…”

“…x 100% Diameter zona hambat positif kontrol Hasil aktivitas antibakteri yang diperoleh dari rumus tersebut akan digolongkan menjadi tiga yaitu: kuat apabila persentase kemampuan penghambatan  70 %, sedang apabila persentase kemampuan penghambatan berada dalam kisaran 50-70% dan lemah apabila persentase kemampuan penghambatan <50% (Ikhtiarudin et al, 2020) Prosedur kerja ini telah lolos uji etik dengan nomor: KE/1039/09/2019, yang dikeluarkan oleh Komisi Etik Kedokteran Universitas Gadjah Mada.…”