Sintesis dan Potensi Aktivitas Tabir Surya Senyawa Analog Kalkon Turunan 3’-Hidroksiasetofenon dan 4-Metoksibenzaldehid

Ikhtiarudin, Ihsan; Agistia, Nesa; Harlianti, Tria; Zamri, Adel

doi:10.37859/jp.v10i1.1541

Cited by 4 publications

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“…Selanjutnya, sinyal doublet dari proton Hα dan Hβ pada senyawa C345 berturut-turut muncul pada pergeseran kimia 7,52 dan 7,83 ppm, masing-masing dengan nilai tetapan penjodohan (coupling constant) sebesar 15,5 Hz. Berdasarkan nilai tersebut dapat disimpulkan bahwa senyawa C345 memiliki konfigurasi trans atau (E) (Ikhtiarudin et al, 2019;Zamri et al, 2016). Sinyal-sinyal yang muncul pada daerah proton aromatik senyawa C345 ini ditampilkan dengan lebih detail pada Gambar S1 9 (Lihat Supporting Information).…”

Section: Perbandinganunclassified

Sintesis, Karakterisasi Struktur, dan Kajian In Silico Potensi 2'-Hidroksicalkon dan Flavonol Ter¬¬¬substitusi Trimetoksi sebagai Inhibitor Main Protease (MPro) SARS-CoV-2

Ikhtiarudin,

Frimayanti,

Nasution

et al. 2024

ALCHEMY J. Pen. Kim

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Pada penelitian ini, 2'-hidroksicalkon (C345) dan flavonol (F345) tersubstitusi trimetoksi telah disintesis menggunakan metode iradiasi microwave dan metode pengadukan. Struktur kedua produk telah dikarakterisasi melalui analisis spektroskopi UV-Vis, FT-IR, 1H NMR, 13C NMR, dan HRMS. Hasil analisis spektroskopi menunjukkan bahwa kedua produk memiliki struktur yang sesuai dengan struktur molekul target yang diharapkan. Selain itu, hasil sintesis juga menunjukkan bahwa metode iradiasi microwave terbukti dapat mempercepat waktu reaksi (dari 1,5-3,0 jam menjadi 3-6 menit) dan meningkatkan rendemen produk murni pada sintesis senyawa C345 (55,31 %) dan F345 (83,65 %). Selanjutnya, hasil docking menunjukkan bahwa kedua senyawa dapat membentuk ikatan hidrogen dengan beberapa residu penting pada sisi aktif dan dapat terikat pada kedua situs katalik MPro SARS-CoV-2 (PDB ID:6M2N), yaitu His41 dan Cys145 melalui interaksi hidrofobik dengan nilai energi bebas pengikatan yang lebih negatif (-8,95 dan -9,02 kcal/mol) dibandingkan dengan baicalein sebagai inhibitor pembanding. Hasil kajian in silico lainnya juga menunjukkan bahwa kedua senyawa memiliki profil farmakokinetik yang baik dan memiliki sifat kemiripan dengan obat berdasarkan aturan Lipinski, Ghose, Veber, Egan, dan Muegge. Selain itu, senyawa F345 juga diprediksi memiliki risiko toksisitas yang lebih kecil dibandingkan dengan baicalein. Synthesis, Structural Characterization, and In Silico Study of the Potential of 2'-Hydroxychalcone and Trimethoxy-Substituted Flavonols as Inhibitors of the Main Protease (MPro) of SARS-CoV-2. In this study, trimethoxy-substituted 2'-hydroxychalcone (C345) and flavonol (F345) were synthesized using microwave irradiation and stirring methods. The structure of the two products were characterized by spectroscopic analyses including UV-Vis, FT-IR, 1H NMR, 13C NMR, and HRMS. The result of spectroscopic analyses showed that the products had structures consistent with the expected target molecules. In addition, the synthesis results showed that the microwave irradiation method was proven to speed up the reaction time (from 1.5-3.0 hours to 3-6 minutes) and increased the yield of pure product in the synthesis of compounds C345 (55.31 %) and F345 (83.65 %). Furthermore, the docking result showed that the two compounds can form hydrogen bonds with several important residues on the active site and also can bind to catalytic dyad of the SARS-CoV-2 MPro (PDB ID:6M2N), namely His41 and Cys145 through hydrophobic interactions with a more negative binding free energy (-8.95 and -9.02 kcal/mol) than baicalein as a reference inhibitor. The result of silico studies also showed that the two compounds exhibited good pharmacokinetic profiles and drug-likeness properties based on Lipinski, Ghose, Veber, Egan, and Muegge rules. In addition, compound F345 was also predicted to has a smaller toxicity risk compared to baicalein.

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Section: Perbandinganunclassified

Sintesis, Karakterisasi Struktur, dan Kajian In Silico Potensi 2'-Hidroksicalkon dan Flavonol Ter¬¬¬substitusi Trimetoksi sebagai Inhibitor Main Protease (MPro) SARS-CoV-2

Ikhtiarudin,

Frimayanti,

Nasution

et al. 2024

ALCHEMY J. Pen. Kim

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“…Then, the latest research shows that the analog chalcone (E )-1-( 3h ydroxyphenyl)-3 -( 4 -methoxyphenyl)prop-2-en-lone has the potential to be developed as an active ingredient in sunblock preparations at a concentration of 200 pg / mL with an SPF value of 30.6 iiO. 38 [ 7 ].…”

Section: Sunscreen; Disk Diffusionmentioning

confidence: 99%

“…Determination of %Te and %Tp values were conducted by modifying the previous method [ 7 ]. A total of 10 mg of sample was dissolved in 10 mL absolute ethanol to obtain the mother liquor with a concentration of 1000 pg / mL.…”

Section: 1 Determination Of %Te and %Tp Valuesmentioning

confidence: 99%

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

Ikhtiarudin¹,

Agistia²,

Frimayanti³

et al. 2020

J. Kim. Sains Apl.

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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.

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“…Research on the development of sunscreen compound products is currently being carried out. One of the essential oils that can be used to make SPF is a chalcone derivatives (Barbulova, Colucci, & Apone, 2015;Cefali, Ataide, Moriel, Foglio, & Mazzola, 2016;Ikhtiarudin, Agistia, Harlianti, & Zamri, 2019).…”

Section: Introductionmentioning

confidence: 99%

Computational Study Potency of Eugenol and Safrole Derivatives as Active Sunscreen Material

Male

Sutapa

Maahury

et al. 2022

molekul

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Computational studies have been carried out on eugenol and safrole derivatives as active sunscreen materials. The calculations were using Density Functional Theory (DFT) with the B3LYP functional and basis set 6-31G (d). The calculated eugenol derivative i.e. 3,4-dimethoxy isobutyl cinnamate; 3,4-dimethoxy isoamyl cinnamate; 3,4-dimethoxy isohexyl cinnamate; 3,4 dimethoxy isoheptyl cinnamate; 3,4-dimethoxy isoctyl cinnamate. The calculated safrole i.e. 3,4-methylenedioxy isobutyl cinnamate; 3,4-methylenedioxy isoamyl cinnamate; 3,4-methylenedioxy isohexyl cinnamate; 3,4-methylenedioxy isoheptyl cinnamate; and 3,4-methylenedioxy isooctyl cinnamate. The main parameter in determining the potential of sunscreen compounds is energy gap. The results of computational calculations show that the 3,4-methylenedioxy isohexyl cinnamate has the smallest energy gap (HOMO-LUMO) of 0.15021 eV. This shows that 3,4-methylenedioxy isohexyl cinnamate has a better potential as an active sunscreen material. In addition, the elongation of the alkyl chain does not significantly affect the HOMO-LUMO energy difference

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Sintesis dan Potensi Aktivitas Tabir Surya Senyawa Analog Kalkon Turunan 3’-Hidroksiasetofenon dan 4-Metoksibenzaldehid

Cited by 4 publications

References 0 publications

Sintesis, Karakterisasi Struktur, dan Kajian In Silico Potensi 2'-Hidroksicalkon dan Flavonol Ter¬¬¬substitusi Trimetoksi sebagai Inhibitor Main Protease (MPro) SARS-CoV-2

Sintesis, Karakterisasi Struktur, dan Kajian In Silico Potensi 2'-Hidroksicalkon dan Flavonol Ter¬¬¬substitusi Trimetoksi sebagai Inhibitor Main Protease (MPro) SARS-CoV-2

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

Computational Study Potency of Eugenol and Safrole Derivatives as Active Sunscreen Material

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