Marcellino Rudyanto
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Airlangga University, Jl. Dharmawangsa Dalam, Surabaya 60286, Indonesia
Articles
6
Documents
Metode Baru Pembuatan Metil 4-Iodobutirat

Majalah Farmasi Airlangga Vol 8, No 2 (2010): Majalah Farmasi Airlangga
Publisher : Majalah Farmasi Airlangga

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Abstract

Methyl 4-iodobutyrate is an important reagent for the syntheses of biologically active natural products, e.g. in the conversion of cassiarin A to cassiarin B. This paper describes a new method for the preparation of methyl 4-iodobutyrate from g-butyrolactone, employing Samuelsson reaction. In the first step g-butyrolactone was treated with sodium methoxide to give methyl 4-hydroxybutyrate which was then treated with triphenylphosphine, imidazole, and iodine in the second step to give methyl 4-iodobutyrate. The obtained compounds were analyzed by IR, 1H-NMR, 13C-NMR and mass spectroscopies. Methyl 4-iodobutyrate was prepared in two steps from g-butyrolactone in 55% overall yield. Keywords: methyl 4-iodobutyrate, g-butyrolactone, Samuelsson Reaction.

SYNTHESIS OF SOME CINNAMIC ACID DERIVATIVES: EFFECT OF GROUPS ATTACHED ON AROMATIC RING TO THE REACTIVITY OF BENZALDEHYDE

Indonesian Journal of Chemistry Vol 8, No 2 (2008)
Publisher : Universitas Gadjah Mada

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Abstract

Synthesis of cinnamic acid and its six derivatives has been done by employing Knoevenagel reaction. Benzaldehyde, 4-butylbenzaldehyde, 4-t-butylbenzaldehyde, 4-butoxybenzaldehyde, 4-phenylbenzaldehyde, 5-bromo-2,4-dimethoxybenzaldehyde, and 5-bromo-2,3-dimethoxybenzaldehyde were reacted with malonic acid in pyridine – piperidine to give cinnamic acid (85,3%), 4-butylcinnamic acid (69,3%), 4-t-butylcinnamic acid (77,7%), 4-butoxycinnamic acid (64,5%), 4-phenylcinnamic acid (65,5%), 5-bromo-2,4-dimethoxycinnamic acid (53,2%) and 5-bromo-2,4-dimethoxycinnamic acid (57,2%), respectively. It was disclosed that 4-alkyl, 4-alkoxy, 4-aryl, dan 2-alkoxy groups decrease the reactivity of carbonyl carbon of benzaldehyde.   Keywords: cinnamic acid, cinnamic acid derivatives, Knoevenagel reaction

Structure Modification of Ethyl p-methoxycinnamate Isolated from Kaempferia galanga Linn. and Citotoxicity Assay of The Products on WiDr Cells

Indonesian Journal of Cancer Chemoprevention Vol 1, No 1 (2010)
Publisher : Indonesian Research Gateway

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Abstract

Ethyl p-methoxycinnamate, major ingredient of Kaempferia galanga rhizome, have been reported not only has analgesic – anti inflammatory activities like NSAIDs which inhibited cyclooxygenase, but also inhibit tumor cell proliferation in specimen of mouse epidermis. Therefore, it will be interesting to carry out  synthetic studies on the derivates of ethyl  p-methoxycinnamate and searching their citotoxic activity on WiDr cell. We wish to report of structure modification on carboxyl moiety of  ethyl p-methoxycinnamate  and  evaluation on their citotoxic activity  on WiDr cell. Isolation of ethyl p-methoxycinnamate from Kaempferia galanga rhizome was carried out by percolation with ethanol 96% as solvent. Hydrolysis of ethyl p-methoxycinnamate in basic condition was performed to obtain p-methoxycinnamic acid. Preparation of some thiourea derivates of ethyl  p-methoxycinnamate was carried out  by microwave irradiation. Citotoxicity assay was carried out by MTT method for 48 h.   Modification  of  carboxyl  group  of  ethyl  p-methoxycinnamate to its thiourea form could be carried out by microwave irradiation gave; (E)-3-(4-methoxyphenyl)-N-(phenylcarba- mothioyl)acrylamide (50%); (E)-3-(4-methoxyphenyl)-N-(4-methoxyphenylcarbamothi- oyl)acrylamide (26%) and (E)-3-(4-methoxyphenyl)-N-(4-methylphenylcarbamothioyl) acrylamide (54%), yield calculated for 2 step from the acid chloride. All compounds showed no citotoxic effect on WiDr cell at 48 h incubation.

SINTESIS N-3-CHLOROBENZOYLAMOXICILLIN DAN UJI AKTIVITAS ANTIBAKTERINYA TERHADAP Pseudomonas aeruginosa ATCC 27853

Farmasains Vol 1, No 2 (2011): Oktober 2010 - Maret 2011
Publisher : UMM Press

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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.

SYNTHESIS OF SOME CINNAMIC ACID DERIVATIVES: EFFECT OF GROUPS ATTACHED ON AROMATIC RING TO THE REACTIVITY OF BENZALDEHYDE

Indonesian Journal of Chemistry Vol 8, No 2 (2008)
Publisher : Universitas Gadjah Mada

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Abstract

Synthesis of cinnamic acid and its six derivatives has been done by employing Knoevenagel reaction. Benzaldehyde, 4-butylbenzaldehyde, 4-t-butylbenzaldehyde, 4-butoxybenzaldehyde, 4-phenylbenzaldehyde, 5-bromo-2,4-dimethoxybenzaldehyde, and 5-bromo-2,3-dimethoxybenzaldehyde were reacted with malonic acid in pyridine – piperidine to give cinnamic acid (85,3%), 4-butylcinnamic acid (69,3%), 4-t-butylcinnamic acid (77,7%), 4-butoxycinnamic acid (64,5%), 4-phenylcinnamic acid (65,5%), 5-bromo-2,4-dimethoxycinnamic acid (53,2%) and 5-bromo-2,4-dimethoxycinnamic acid (57,2%), respectively. It was disclosed that 4-alkyl, 4-alkoxy, 4-aryl, dan 2-alkoxy groups decrease the reactivity of carbonyl carbon of benzaldehyde.   Keywords: cinnamic acid, cinnamic acid derivatives, Knoevenagel reaction

ONE-STEP CONVERSION OF EUGENOL TO METHYL ISOEUGENOL USING MICROWAVE IRRADIATION IN SOLVENT-FREE CONDITIONS

Indonesian Journal of Chemistry Vol 6, No 3 (2006)
Publisher : Universitas Gadjah Mada

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Abstract

A research on conversion of eugenol to methyl isoeugenol via one-step reaction with microwave irradiation has been carried out. Mixtures containing eugenol, sodium or potassium carbonate as solid support, with or without sodium or potassium hydroxide as base, with or without tetrabutylammonium bromide as phase transfer catalyst, with dimethyl sulfate as the methylating agent were irradiated in a domestic microwave oven for 20 - 50 seconds. It was revealed that one-step methylation and isomerization required combinations of sodium or potassium hydroxide base and tetrabutylammonium bromide. Without combination of base and TBAB only one product, i.e. methyl eugenol, was formed.   Keywords: eugenol, methyl eugenol, methyl isoeugenol, microwave