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All Journal Farmasains : Jurnal Farmasi dan Ilmu Kesehatan Berkala Ilmiah Kimia Farmasi
Marcellino Rudyanto
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Biochemistry, Genetics & Molecular Biology Chemistry Medicine & Pharmacology

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SINTESIS N-3-CHLOROBENZOYLAMOXICILLIN DAN UJI AKTIVITAS ANTIBAKTERINYA TERHADAP Pseudomonas aeruginosa ATCC 27853 Ika T. D. Kusumowati Siswandono; Marcellino Rudyanto
Farmasains : Jurnal Farmasi dan Ilmu Kesehatan Vol. 1 No. 2 (2011): Oktober 2010 - Maret 2011
Publisher : Universitas Muhammadiyah Malang

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22219/far.v1i2.1166

Abstract

N-3-chlorobenzoylamoxicillin were prepared by reacting 3-chlorobenzoylchloride with amine group of amoxicillin (acylation reaction). The reaction is nucleophilic substitution reaction in which primary amine group of the amoxicillin, which was nucleophilic in nature, attack C=O groups of benzoyl chloride-derivatives which has positive charge. The results showed that percentages of N-3-chlorobenzoylamoxicillin were 75%, respectively. Rf value of the resulting compounds different from Rf value of the amoxicillin. The structures were identified by Infra Red Spectrophotometry and Nuclear Magnetic Resonance (1H-NMR) Spectrometry. The results of the spectral analysis showed that spectra of amoxicillin and N-3-chlorobenzoylamoxicillin had changed significantly. The resulting structure was well fitted to the expected compounds. Antibacterial activities of N-3-chlorobenzoylamoxicillin­ against Pseudomonas aeruginosa ATCC 27853 were tested using dilution method. Minimum Inhibition Concentration achieved in the research represented the lowest level that can inhibit bacterial growth adequately. Analysis of the Minimum Inhibition Concentration on Pseudomonas aeruginosa ATCC 27853 showed significant differences between amoxicillin and N-3-chlorobenzoylamoxicillin.
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.  
Co-Authors Ika T. D. Kusumowati Siswandono Juni Ekowati Ruri Intan Nurcahyaningtyas