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Molecular Docking of Michelia alba Leaves Active Compounds Against Human Epidermal Growth Factor Receptor 2 (HER-2) Isman, Felysia; Pratama, Paundra; Fadlan, Arif
Al-Kimia Vol 10 No 2 (2022): DECEMBER
Publisher : Study Program of Chemistry - Alauddin State Islamic University of Makassar

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.24252/al-kimia.v10i2.28437

Breast cancer characterized by overexpression of the human epidermal growth factor receptor-2 (HER-2) and is a deadly disease worldwide. Chemotherapy with drugs targeting HER-2 is less effective and shows various drawbacks. This study aimed to study anticancer potential of active compounds contained in Michelia alba through molecular docking against HER-2. The molecular docking study was performed toward HER-2 receptor (PDB: 3PP0) containing 30Q native ligand with MCULE. The results showed that cis-linalool oxide, trans-linalool oxide, linalool, β-elemena, α-humulene, and nerolidol contained in M. alba leaves had lower docking scores than quercetin as control. Nerolidol showed the lowest docking score among all compounds. The active compounds in the leaves of M. alba have the potential as a HER-2 inhibitor in silico.

Molecular Docking of Acetylacetone-Based Oxindole Against Indoleamine 2,3-Dioxygenase: Study of Energy Minimization Josaphat, Frans; Fadlan, Arif
Walisongo Journal of Chemistry Vol 6, No 2 (2023): Walisongo Journal of Chemistry
Publisher : Department of Chemistry Faculty of Science and Technology Walisongo

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.21580/wjc.v6i2.17638

Molecular docking plays an essential role in drug discovery because it is more efficient and more affordable compared to traditional synthesis methods and biological assays. Molecular docking determines the conformation and affinity of non-covalent bonds between macromolecules (receptors) and small molecules (ligands) computationally. Energy minimization carried generally out by using the Merck Molecular Force Field 94 (MMFF94) force field produces ligands with the most stable conformation. MarvinSketch and Open Babel for energy minimization were utilized in this docking study of acetylacetone-based oxindole derivatives to 2,3-dioxygenase indoleamine macromolecules (IDO-1, PDB: 2D0T). The results showed that MarvinSketch provides better binding energy than energy minimization with Open Babel. Molecular docking indicated different interactions between 2D0T macromolecule residues with ligands that have been prepared using MarvinSketch, Open Babel, and without energy minimization.

In silico studies of isatinyl-2-aminobenzoylhydrazone transition metal complexes against cyclin-dependent kinase 6 (CDK6) Nusantoro, Yesaya Reformyada; Fadlan, Arif
Pharmacy Reports Vol. 1 No. 1 (2021): Pharmacy Reports
Publisher : Indonesian Young Scientist Group and UPN Veteran Jakarta

Cyclin-dependent kinase 6 (CDK6) is an important member of protein kinases, involving in many cellular pathways especialy cell cycle progression. Thus, CDK6 is a promising target in cancer therapy. This report aims to predict inhibiton of CDK6 by some complex compounds by using molecular docking and pharmacological properties analysis. Those compounds are isatinyl-2-aminobenzoylhydrazone (ISABH) and cobalt (II), nickel (II), copper (II), and zinc (II) transition metal complexes. The molecular docking against CDK6 (PDB code: 3NUP) revealed that ISABH/ISABH-transition metal complexes established ligand-protein interaction as expressed by negative binding affinity values. Drug-likeness by SwissADME indicated that ISABH and Ni-ISABH met the Lipinski’s rule of five. Both compounds also showed reasonable pharmacological criteria by admetSAR.

DIFFERENT ROUTES FOR THE SYNTHESIS OF BENZALDEHYDE-BASED DIHYDROPYIMIDINONES VIA BIGINELLI REACTION Ilfahmi, Yan Alamanda; Fadlan, Arif
Jurnal Kimia Riset Vol. 8 No. 2 (2023): December
Publisher : Universitas Airlangga, Campus C Mulyorejo, Surabaya, Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20473/jkr.v8i2.45209

Multicomponent reactions involving three or more reactants are commonly used to prepare dihydropyrimidinone with various bioactivities. This study reports the different routes for the synthesis of benzaldehyde-based dihydropyrimidinone via the Biginelli reaction and investigates the yield of the obtained products. The synthesis was performed via routes A, B, C, D, and E based on the formation of iminium, enamine, and Knoevenagel intermediates between urea, benzaldehyde, and ethyl acetoacetate. Route A, through a one-pot reaction via iminium, produced dihydropyrimidinone with a yield of 58%. The product from route B via iminium was obtained in 62% yield. Route C and D occurred via enamine at room temperature, and reflux gave the product 31% and 40% yield, respectively. Route E involving Knoevenagel intermediate provided the product in a 38% yield. 1H NMR, FTIR, and MS spectroscopic techniques were used for structure elucidation.

ISOLATION OF ETHYL TRANS-P-METHOXYCINNAMATE FROM Kaempferia galanga L. RHIZOMES BY USING N-HEXANE Ingeswari, Aulya Vidiana; Khozin, Muhamad Nur; Fadlan, Arif; Santoso, Mardi; Nugraheni, Zjahra Vianita; Sarmoko
Jurnal Kimia Riset Vol. 9 No. 1 (2024): June
Publisher : Universitas Airlangga, Campus C Mulyorejo, Surabaya, Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20473/jkr.v9i1.58165

Kaempferia galanga L. rhizomes contain ethyl trans-p-methoxycinnamate as a major secondary metabolite compound and biomarker. Various extraction methods with different solvents can isolate ethyl trans-p-methoxycinnamate with potential bioactivities. This paper reported the isolation of ethyl trans-p-methoxycinnamate from two varieties of K. galanga L. rhizomes by maceration in n-hexane. The small and large varieties of K. galanga samples produced ethyl trans-p-methoxycinnamate in 1.43% and 1.84% yields, higher than other methods and polar solvents of previous research. Structural elucidation of the obtained ethyl trans-p-methoxycinnamate was performed by FTIR, MS, and 1H NMR spectroscopies.

Sintesis Etil 2-(4-Formilfenoksi)asetat melalui Substitusi Gugus Hidroksil 4-Hidroksibenzaldehida Fadlan, Arif; Nurhasan, Moch.
Chimica et Natura Acta Vol 12, No 3 (2024)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.24198/cna.v12.n3.50210

Senyawa 4-hidroksibenzaldehida merupakan salah satu senyawa fenolat yang mengandung gugus aldehida dan dapat mengalami transformasi struktur melalui berbagai reaksi kimia menghasilkan produk dengan aktivitas biologis yang potensial. Pada penelitian ini struktur senyawa 4-hidroksibenzaldehida dimodifikasi melalui substitusi gugus hidroksil oleh etil kloroasetat dengan perbandingan mol 6:10 (metode A), 5:10 (metode B), dan 2,5:10 (metode C) menghasilkan etil 2-(4-formilfenoksi)asetat. Spektroskopi resonansi magnetik inti 1H dan 13C NMR, inframerah, dan massa digunakan untuk menetapkan struktur hasil sintesis. Hasil penelitian menunjukkan bahwa metode B memberikan produk berupa padatan berwarna putih dengan yield sebesar 70% yang lebih tinggi dibandingkan metode A (yield 23%) dan metode C (yield 47%). Pembentukan etil 2-(4-formilfenoksi)asetat diusulkan terjadi melalui substitusi nukleofilik bimolekular (SN2).

Study of Synthesis of Ethyl-2-(4-Allyl-2-Methoxyphenoxy)Acetate in Polar Aprotic Solvents Fadlan, Arif; Masitoh, Heni; Niadisti, Bella Ratih Apsari; Khusnayaini, Intan Ali; Agustin, Lela; Roshuna, Jean Fitriani
Walisongo Journal of Chemistry Vol. 7 No. 2 (2024): Walisongo Journal of Chemistry
Publisher : Department of Chemistry Faculty of Science and Technology Walisongo

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.21580/wjc.v7i2.23970

Eugenol, a phenol-derived aromatic allylbenzene compound, exhibits a wide spectrum of biological activities (antifungal, antibacterial, antioxidant, analgesic, and antiseptic) and is an active ingredient in various hygiene products. It contains three reactive groups (hydroxy, allyl, and methoxy) and undergoes several reactions, including alkylation. The modification of the hydroxyl group of eugenol through alkylation has been performed using different alkylating agents. Alkylation has been carried out in various solvents (benzene, acetonitrile, methanol, and water) and at diverse temperatures. Hence, the investigation of this alkylation reaction on eugenol remains challenging. Correspondingly, the present study investigated the alkylation of eugenol by ethyl chloroacetate in polar aprotic solvents (N,N-dimethylformamide, dimethyl sulfoxide, acetonitrile, and tetrahydrofuran) at temperatures ranging from 0°C to room temperature. The product, ethyl 2-(4-allyl-2-methoxyphenoxy)acetate (3), was obtained in yields of 91%, 51%, and 47% using DMF, DMSO, and CH3CN, respectively. The product's structure was confirmed by NMR, IR spectroscopy, and HRESIMS analysis.

Study of Synthesis of Ethyl-2-(4-Allyl-2-Methoxyphenoxy)Acetate in Polar Aprotic Solvents Fadlan, Arif; Masitoh, Heni; Niadisti, Bella Ratih Apsari; Khusnayaini, Intan Ali; Agustin, Lela; Roshuna, Jean Fitriani
Walisongo Journal of Chemistry Vol. 7 No. 2 (2024): Walisongo Journal of Chemistry
Publisher : Department of Chemistry Faculty of Science and Technology UIN Walisongo

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.21580/wjc.v7i2.23970

Eugenol, a phenol-derived aromatic allylbenzene compound, exhibits a wide spectrum of biological activities (antifungal, antibacterial, antioxidant, analgesic, and antiseptic) and is an active ingredient in various hygiene products. It contains three reactive groups (hydroxy, allyl, and methoxy) and undergoes several reactions, including alkylation. The modification of the hydroxyl group of eugenol through alkylation has been performed using different alkylating agents. Alkylation has been carried out in various solvents (benzene, acetonitrile, methanol, and water) and at diverse temperatures. Hence, the investigation of this alkylation reaction on eugenol remains challenging. Correspondingly, the present study investigated the alkylation of eugenol by ethyl chloroacetate in polar aprotic solvents (N,N-dimethylformamide, dimethyl sulfoxide, acetonitrile, and tetrahydrofuran) at temperatures ranging from 0°C to room temperature. The product, ethyl 2-(4-allyl-2-methoxyphenoxy)acetate (3), was obtained in yields of 91%, 51%, and 47% using DMF, DMSO, and CH3CN, respectively. The product's structure was confirmed by NMR, IR spectroscopy, and HRESIMS analysis.

Synthesis of 1,2-Di(phenyl)ethan-1,2-dione through Oxidation of 2-Hydroxy-1,2-Dipheniletanone by using Copper(II) Citrate Seviani, Winda; Fadlan, Arif; Wirastuti, Vania
Chimica et Natura Acta Vol 13, No 2 (2025)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.24198/cna.v13.n2.50263

1,2-Di(phenyl)-1,2-dione widely used in chemical and pharmaceutical industries and found as a framework in secondary metabolites can be obtained through oxidation of 2-hydroxy-1,2-diphenylethanone using strong acids, homogeneous, heterogeneous, and metal catalysts. However, these oxidation methods exhibit various drawbacks. This study reported the oxidation of 2-hydroxy-1,2-diphenylethanone by using copper(II) citrate to produce 1,2-di(phenyl)-1,2-dione. The oxidation performed with copper(II) citrate and ammonium nitrate in glacial acetic acid as solvent yielded 1,2-di(phenyl)-1,2-dione in 88% yield higher than the nitric acid method (79% yield). The FTIR, NMR spectriscopies, and mass analysis confirmed the structure of 1,2-di(phenyl)ethane-1,2-dione. The oxidation of 2-hydroxy-1,2-diphenylethanone using copper(II) citrate is proposed by the formation of Cu⁺ ions and a resonance-stabilized 2-hydroxy-1,2-diphenylethanone radical resulting in 1,2-di(phenyl)ethane-1,2-dione.

Modifikasi Struktur Eugenol Menjadi Etil 2-(4-Alil-2-Metoksifenoksi) Asetat Melalui Reaksi Alkilasi dengan Etil Kloroasetat Agistya, Hamida Azza; Fadlan, Arif; Masitoh, Heni
Jurnal Tumbuhan Obat Indonesia Vol. 18 No. 1 (2025): July 2025
Publisher : Universitas Tidar

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.31002/jtoi.v18i1.1045

Eugenol, a natural product with broad and promising biological activity, possesses three reactive functional groups of hydroxyl, allyl, and methoxy, which can be transformed through chemical reactions into various derivatives. The reaction of eugenol and ethyl chloroacetate with a mole ratio of 1:1 has been reported to produce an alkylation product. However, the use of dry acetone as a solvent and the reflux condition for 12 hours were the drawbacks of this reaction. The structural modification of eugenol into ethyl 2-(4-allyl-2methoxyphenoxy) acetate as an alkylation product was further studied in this paper. The alkylation reaction of eugenol and ethyl chloroacetate was performed in dimethylformamide with a mole ratio of 6:10 (method A), 1:1 (method B), 1:4 (method C), and 1:4 (method D) at room temperature (methods A and D) and under reflux conditions (methods B and C). The results showed that the alkylation reaction with a mole ratio of 1:4 at room temperature (method D) produced ethyl 2-(4-allyl-2-methoxyphenoxy)acetate as a pure compound with a yield of 94%. The structure of the alkylation product was determined by FTIR, NMR spectroscopy, and mass analysis. Ethyl 2-(4-allyl-2-methoxyphenoxy)acetate is a key compound in the development of various eugenol-derived active compounds.

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