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Journal : Berkala Ilmiah Kimia Farmasi

The Effect of Methyl and Chloro Substituent Compounds in Amida Derivatives Synthesis from p-Metoxicynamic Acid with Microwaves Irradiation Ruri Intan Nurcahyaningtyas; Juni Ekowati Ekowati; Marcellino Rudyanto
Berkala Ilmiah Kimia Farmasi Vol. 7 No. 2 (2020): DESEMBER
Publisher : Universitas Airlangga

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (304.52 KB) | DOI: 10.20473/bikfar.v7i2.29300

Abstract

Background: The difference in the nature of these aromatic amine substituents, i.e. methyl and chloro will affect the N atom of aniline as a nucleophile to attack the carbonyl C atom in the p-methoxcycinnamoyl chloride in the synthesis two amides derivate of p-methoxycinnamic acid, namely N-(p-methylphenyl)-p-methoxycinnamide and N-(p-chlorophenyl)-p-methoxycinnamide. Aim: to obtain the N-(p-methylphenyl)-p-methoxycinnamide and the N-(p-chlorophenyl)-p-metoxicinamide compound from p-methoxycinamic acid using the microwave irradiation method as source of energy. Beside that, it also to determine the effect of the presence of methyl and chloro substituents in para position of aromatic amines in the yields of reactions. Method: The reactions were carried out by microwave irradiation at three powers, i.e 120 watts, 200 watts, 280 watts. After separation and purification steps, the products were identified by spectrometric methods. Result: At power of 200 watts for reaction time of 7.5 minutes, the yield of N-(p-methylphenyl)-p-methoxycinamide is larger than N-(p-chlorophenyl)-p-methoxycinnamamide. The percentage of the product synthesis of N-(p-methylphenyl)-p-methoxycinamide was 51.84% and the percentage of N-(p-chlorophenyl)-p-methoxycinnamamide was to 47.20%. Conclusion: The effect of substituent methyl is increase the percentage yield of N-(p-methylphenyl)-p-methoxycinamide compound than that substituent chloro of N-(p-chlorophenyl)-p-methoxycinamide compound under the same reaction conditions. Based on the identification of the structure of the synthesized compound using a UV spectrophotometer, infrared spectrophotomers and 1H-NMR spectrometer it can be concluded that the synthesized compounds are N-(p-methylphenyl)-p-methoxycinnamide and N- (p-chlorophenyl)-p-methoxycinnamide.  
Synthesis of Methyl 3-(4-hydroxyphenyl) acrylate using Domestic Microwave Irradiation at 200 Watt Power Moch Davit Abdul Majid; Ekowati, Juni; Purwanto, Bambang Tri
Berkala Ilmiah Kimia Farmasi Vol. 10 No. 2 (2023): December
Publisher : Universitas Airlangga

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20473/bikfar.v10i2.38479

Abstract

In this study, a methylation reaction was carried out for the p-coumaric acid compound using potassium carbonate as a base and dimethyl carbonate as a methylation agent with acetone as a solvent. The methylation reaction was carried out using microwave irradiation from microwave domestic with a power of 200 watts. The purity test was carried out on a TLC plate using three different eluents and produced a single stain that was different from the initial compound. The phenol functional group tested with FeCl3 reagent showed a positive purple color. Compound identification was done using an FT-IR spectrophotometer and a 1H-NMR spectrometer. In the synthesized FT-IR spectrum, there was an absorption of the ester group at wave numbers 1671 cm-1 (C=O group) and 1243 cm-1 (C-O group), there was a band at 3378 cm-1 indicating the presence of the phenol group. There were differences in fingerprint results in the FT-IR spectrum of the p-coumaric acid compound and the results of the methylation reaction. The 1H-NMR spectrum confirmed the presence of three methyl ester protons of the carboxylic acid and the phenolic OH. This indicated that the synthesis produced a compound, namely methyl (E)-3-(4-hydroxyphenyl) acrylate. Keywords: methyl (E) 3-(4hydroxyphenyl) acrylate), p-coumaric acid, Potasium Carbonate, Microwave Irradiation, Synthesis
Effect of para (p) Position Methoxy Group on The Synthesis of Benzohydrazide Derivatives from Methylbenzoate Starting Material Suzana, Suzana; Ardhayanti, Erlina; Amalia Novianti, Kholis; Ekowati, Juni; Budiati, Tutuk
Berkala Ilmiah Kimia Farmasi Vol. 9 No. 2 (2022): December
Publisher : Universitas Airlangga

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20473/bikfar.v9i2.42705

Abstract

The synthesis of N'-benzylidenebenzohydrazide and N'-(4-methoxybenzylidene)benzohydrazide was performed through a condensation reaction. The reaction was performed in two stages with methylbenzoate as the initial material. In the first phase, benzohydrazide was obtained by reacting methylbenzoate and hydrazine hydrate; in the second phase, the compounds N'-benzylidenebenzohydrazide and N'-(4- methoxybenzylidene)benzohydrazide were obtained by reacting benzohydrazide and benzaldehyde/4- methoxybenzaldehyde. The results obtained were 87% and 92%, respectively. A purity test was done by thin layer chromatography (TLC) and melting point determination. The melting point of benzohydrazide was 108-111°C, N'-benzylidenebenzohydrazide had a melting point of 104-108°C, and N'-(4- methoxybenzylidene)benzohydrazide had a melting point of 159-161°C. The synthesized compounds were identified by UV-VIS, FT-IR, and 1H-NMR spectroscopy. Keywords: Synthesis, N' -benzylidenebenzohydrazide, N’- (4-methoxybenzylidene)benzohydrazide, methylbenzoate
Molecular Docking Study of Ferulic Acid Analog Compounds as Lung Antifibrotic at TGF-β1 Receptors Pebrianti, Denayu; Ekowati, Juni; Ainurrizma, Dhea Ananda
Berkala Ilmiah Kimia Farmasi Vol. 10 No. 1 (2023): June
Publisher : Universitas Airlangga

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20473/bikfar.v10i1.45430

Abstract

Pulmonary fibrosis was one of the conditions that occurred in Post-COVID Syndrome patients. Development of specific treatment as an agent to treat pulmonary fibrosis was still ongoing. Ferulic acid was a compound that had a potential lung antifibrotic agent through the inhibition of TGF-β1-mediated signaling. Molecular docking studies using the AutoDock Tools program version 1.5.7 were conducted on ferulic acid and its analogs to determine the activity of compounds as antifibrotic. Furthermore, the interaction of the compounds with the receptor was visualized using the Discovery Studio 2021 program. The results showed that ferulic acid and its analogs had lower free energy than Pirfenidone, which was a standard lung antifibrotic drug. 4-Benzoyloxy-3-methoxycinnamic acid was the compound that had the greatest activity. The group that contributed to the ligand-receptor interaction was the aromatic group with π interaction. Keywords:  Molecular Docking, AutoDock, Antifibrotic, TGF-β1, Ferulic Acid
The comparison Study of Synthesis p-Methoxycinnamoylhydrazide by Conventional Thermal Heating and Microwave Irradiation Sulistyowaty, Melanny Ika; Nusandari, Ratna; Rudyanto, Marcellino; Ekowati, Juni
Berkala Ilmiah Kimia Farmasi Vol. 11 No. 1 (2024): June
Publisher : Universitas Airlangga

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20473/bikfar.v11i1.56153

Abstract

Previous studies had shown that ethyl p-methoxycinnamate (EPMS) had various bioactivities, such as analgesic and anti-inflammatory through COX inhibition. Due to its unique structure, this compound was modified into a selective COX-2 inhibitor. In this research, EPMS was isolated from Kaempferia galanga L. and used as a starting material to be reacted with hydrazine hydrate to obtain 3-(4-methoxyfenil)propanehydrazide. This synthesis was carried out using conventional heating and microwave irradiation. The microwave irradiation was chosen because of its potential to reduce reaction time and increase yield. Next, the crude product was purified using column chromatography to produce a pure product, where characterization and structural analyses of the compound were carried out using the TLC test, melting point test, IR, 1H-NMR, and UV spectroscopy. The results showed that the product produced was 3-(4-methoxyphenyl)propanehydrazide with a yield of 0,76% by conventional thermal heating and 7,90% by microwave irradiation. Keywords:  EPMC, Hydrazine Hydrate, 3-(4-Metoxyphenyl)propanehydrazide, Conventional Heating, Microwave Irradiation
Co-Authors AA Sudharmawan, AA Abdul Jabbar, Davano Al Raffi Abdul Rahem, Abdul Achmad Toto Poernomo Achmad Toto Purnomo Adam Hermawan Adi Priatna, Puja Adinda Adelia Wulandari Afandi, Ryan Ainul Yaqin Ainurrizma, Dhea Ananda Akhmad Aminur Rizqia Alief Putriana Rahman Anang Setyo Wiyono Ardhayanti, Erlina Asri Darmawati Bambang Tri Purwanto Bastiana Bastiana Bermawi, Bastiana Dewi Isadiartuti Dewi Melani Hariyadi Dini Retnowati Diyah, Nuzul Wahyuning Diyah, Nuzul Wahyuning Djoko Agus Purwanto Dwi Setyawan Edy Meiyanto Edy Meiyanto Eko Pujiono, Feri Elkania Putri, Safira Engrid Juni Astuti Erika Christy Marentek Esti Hendradi Etik Wahyuningsih Farida Ifadotunnikmah Febrianti, Winanda Rizki Fery Eko Pujiono, Fery Eko Galih Satrio Putra Galih Satrio Putra Ghifari, Aileen Syifa Ghinalya Chalbi Ananda Ghinalya Chalbi Ananda Gusti Rizaldi Hadi Poerwono Handayani, Rosita Hanifah Ridha Rabbani Hariyadi, Dewi Melany Hartono, Thalia Vanessa Heinrich Dengi Hidayati, Shabrina Wahyu I NYOMAN WIJAYA Ichsanto, Farhan Hanang Ida Kristianingsih Ilham Bagus Sagitaras Imamatin Nufus Melania Isnaeni isnaeni, isnaeni isnaeni Isnalita Isnalita, Isnalita Istna Nur’ainul Yaqin Itsna Nur ‘Ainul Yaqin Iwan Sahrial Hamid Kanzaffa, Firly Afnauriza Tedja Kholidah Febriani Kholis Amalia Nofianti Luqmanul Hakim M. Faris Adrianto Mangestuti Agil Marcellino Rudyanto Marcellino Rudyanto Maulia, Arwinda Melanny Ika Sulistyowati Melanny Ika Sulistyowaty Miatmoko, Andang Moch Davit Abdul Majid Mochammad Yuwono Mohammad Rizki Fadhil Pratama Muhamad Ilham Royyan Nafi’ Muhammad Agus Syamsur Rijal Muhammad Faris Adrianto, Muhammad Faris Muhammad Ilham Royyan Nafi Muhammad Yuwono Muhammad Yuwono Muhammad yuwono Muhammad yuwono, Muhammad Yuwono Muhammad Yuwono Naufal, Adam Mochammad Ninis Yuliati, Ninis Noor Erma Nasution Noor Erma Nasution Noor Erma Nasution Noor Erma Nasution Sugijanto Noor Erma Nasution Sugijanto Noorma Rosita Norhayati Norhayati Nusandari, Ratna Paramita, Diajeng Putri Pebrianti, Denayu Poernomo, A.Toto Praditapuspa, Ersanda Nurma Pratama, Adam Prawitasari, Neny Prayoga, Adistiar Pujiono, Ferry Eko Purnomo, Ahmad Toto Purwitasari, Neny Putri Hamidah Khairunnisa Rahman, Ave Rahmana Emran Kartasasmita Rais Razak Ramadhani, Firmansyah Ardian Randiman, Sugijanto Sugijanto Rani, Karina Citra Retno Sari Rian Putra Pratama Rianti, Dian Ratna Riesta Prima Harinastitic Rijal, Agus Syamsur Rossa Auli Tasha Ruri Intan Nurcahyaningtyas Savitri, Orchidea Meidy Nurintan Setiawan, Albertus Aditya SETIAWAN, Catur Dian Setyo Wiyono, Anang Shigeru Sasaki Shigeru Sasaki Shihab, Fawaz Siswandono Siswandono, Siswandono Siswandono, Siswandono Siti Rahmah Soleh, Mochammad Soraya, Yasmin Sovia Aprina Basukia Suciati Suciati Sugijanto Sugijanto Kartosentono Sugijanto Kartosentono Sugijanto Sugijanto Sugijanto Sugijanto Randiman Sugijanto, Noor Erma Nasution Noor Erma Nasution Sukardiman Suko Hardjono Sulistyowati, Melanny Ika Susanto, Julian Dwi Suwarno Putra, Adryansyah Suzana SUZANA, SUZANA Syahrani, Achmad Tahta Amrillah Tiara Puspa Asriningrum Tri Widiandani Tutuk Budiati Tutuk Budiati Ulvan, Angkasa Megistra Widji Soeratri Winantari, Agnes Nuniek Wiwied Ekasari Yaqin, Istna Nur’ainul Yusniasari, Putri Antika Yusuf, Helmy