Synthesis and Antimicrobial Activity Evaluation of Ethyl Salicyl Fumarate and Ethyl Furfuryl Fumarate: Sintesis dan um khasiat anteviikrosa terhadap etil salisil fumarat dan etil furfuril fumarat

This research was conducted in order to synthesize and investigate the antimicrobial activity of ethyl salicyl fumarate and ethyl furfuryl fumarate. These two target molecules were chosen as the former is the derivative of C-9154 antibiotic containing phenolic hydroxyl group, whereas the latter is an example of C9154 antibiotic derivative bearing furan ring instead of benzene. Ethyl salicyl fumarate was synthesized from methyl salicylate through reduction with LiAIH4, condensation of salicyl alcohol with maleic anhydride, and esterification of salicyl maleic acid with ethanol in the presence of benzenesulfonic acid as the catalyst. These reactions gave satisfactory yields (76-92 %) in all steps involved. Similar to this procedure, ethyl furfuryl fumarate was prepared from furfural through reduction with NaBH4 followed by condensation of the resulted furfuryl alcohol with maleic anhydride and esterification of furfuryl maleic acid with ethanol in the presence of benzenesulfonic acid. Although the reduction of furfural and the condensation of furfuryl alcohol with maleic anhydride could be performed smoothly, the esterification of furfuryl maleic acid with ethanol only gave 38 % yield of ethyl furfuryl fumarate. The results of antimicrobial activity test showed that the value of minimum inhibition concentration (M1C) of salicyl maleic acid and ethyl salicyl fumarate towards Staphyllococcus aureus- were 500 and 100 tg/mL, whereas towards Eschericia coil were 2000 and 4000 ag/mL respectively. In contrast, the MIC values of furfuryl maleic acid and ethyl furfuryl fumarate towards Staphyllococcus aureus and Eschericia tali were 150 and 100 p.g/mL respectively. Keywords: synthesis, activity, C-9154 antibiotic, fumarate. ABSTRAK Penelitian ini dilakukan dengan tujuan melakukan sintesis dan uji khasiat antimikroba terhadap etil salisil fumarat dan etil furfuryl fumarat. Kedua molekul target tersebut dipilih dengan pertimbangan bahwa etil salisil fumarat akan merupakan contoh turunan antibiotik C-9154 yang mengandung gugus fenol, sedangkan etil furfuryl fumarat akan menjadi contoh turunan antibiotik C-9154 yang mengikat cincin furan. Etil salisil fumarat disintesis dari metil salisilat melalui reduksi dengan LiAIH4i kondensasi dari salisil alkohoi dengan anhidrida maleat, dan esterifikasi asam salisil maleat dengan etanol menggunakan katalis asam benzenasulfonat. Keseluruhan tahapan reaksi tersebut memberikan rendemen hasil yang memuaskan (76-92 %). Serupa dengan itu, etil furfuril fiunarat disintesis dart furfural melalui reduksi menggunalcan NaBH4 diteruskan dengan kondensasi furfuril alkohol dengan anhidrida maleat dan esterifikasi asam furfuril maleat dengan etanol. Walaupun reduksi furfural dan kondensasi furfuril alkohol dengan anhidrida maleat dapat dilakukan dengan balk, esterifikasi asam furfuril maleat dengan etanol hanya menghasiikan 38 % etil furfuril fumarat. Hasil uji khasiat antimikroba menunjukkan bahwa harga konsentrasi hambatan minimum (MIC) dad asam salisil maleat dan etil salisil fumarat terhadap Slaphyllococcus aureus masing-masing adalah 500 dan 100 ig/mL, sedangkan terhadap Eschericia coli adalah 2000 and 4000 p.g/mL. Sebaliknya, harga MIC dan asam furfuril maleat dan etil furfuril fumarat terhadap Slaphyllococcus aureus dan Eschericia coil masingmasing adalah 150 dan 100 ug/mL. Kata kuaci: sinlesrs, aklivilas, anlibiolik C-9154, fumarat

Sintesis Hidrotalsit Zn-AI-S04sebagai Agen Penukar Anion untuk Aplikasi Pengolahan Polutan Heksasianoferrat (II)

ABSTRACT Synthesis of Zn-AI-S04hydrotalciteand its applicationas anion exchanger for hexacyanoferrat(II) have been studied. Synthesis of Zn-AI-S04 hydrotalcite was carried out by stoichiometric method and hydrothennal treatment. Sulphate in hydrotalcite interlayer was exchanged by hexacyanoferrat (II) that was assumed as pollutant. Kinetics of ion exchange was also investigated. The product of ion exchange was characterized by XRD, IR spectrophotometry and atomic absorption spectrometry. Zn-AI-S04 hydrotalcite can be obtained by stoichiometric method at pH 8 and followed by hydrothennal treatment. The chemical fonnula of the hydrotalcite was Zno.7~/o.26(OH)1.74(S04)o.13.0.52H20.The hexacyanoferrat (II) anion could exchange sulphate in hydrotalcite interlayer as showed by IR spectra and XRD pattems. The anion exchanve capacity was 645.35 meq/100 g, and the kinetics of ion exchange reaction was first order with k = 5 X 1U5 s-. It showed that Zn-AI-Fe(CN)6 could be regenerated easily, so it has been regenerate frequently. Keywords: hydrotalcite, anion exchanger, hexacyanoferra

VIRTUAL SEARCHING OF DUMMYTEMPLATE FOR SINENSETIN BASED ON 2D MOLECULAR SIMILARITY USING CHEMDB TOOL

Sinensetin-like molecules have been searched virtually to find a dummy template for Molecular Imprinted Polymer (MIP) synthesis. The aim of this study is to find a novel adsorbent for Solid Phase Extraction (SPE) of sinensetin based on tailored method using dummy template. Virtual searching was done using ChemDS online c6emical database containing 5 million commercially available chemicals. Sinensetin as target was converted into SMILES code then it was run with threshold of molecular similarity score of 0.5. There were 90 chemical structures given as the output mainly flavone analogue, three flavonols and several non-flavonoidcompounds. The suggested results are three dummy templates that derived from luteolin (flavon) or quercetin (flavonol) with slight alteration by methoxylationprocess

APLIKASI PRINCIPAL COMPONENT REGRESION UNTUK ANALISIS QSAR SENYAWA ANTIOKSIDAN TURUNAN FLAVON/ FLAVONOL MENGGUNAKAN DESKRIPTOR ELEKTRONIK HASIL PERHITUNGAN METODE AM1

Telah dilakukan aplikasi teknik Principal Component Regresion (PCR) untuk analisis hubungan kuantitatif antara struktur elektronik dan aktivitas (QSAR) antioksidan dari senyawa turunan flavon / flavonol. Data aktivitas merupakan data sekunder yang diperoleh dari literatur dan masing-masing dinyatakan sebagai % aktivitas. Representasi struktur kimia berupa deskriptor elektronik meliputi muatan bersih atom dan momen dipol yang diperoleh dari hasil perhitungan metode semiempirik AM1. Evaluasi QSAR yang dilakuakan berupa analisis tahapan Principal Component Analysis (PCA) untuk mengkonversi variabel laten yang dilanjutkan dengan analisis regresi multilinier antara aktivitas dan variabel laten. Hasil penelitian ditunjukkan dengan model persamaan QSAR terpilih dengan menggunakan 4 komponen utama yang dipresentasikan dalam persamaan :%A = 212.2 + (7.196) T1-(20.593)T2-(192.906)T3+(242.706)T4; n=18; 2=0.822 Fhitung/Ftabel=1,397. Kata Kunci: QSAR, Principal Component Analysis, molecular modelin

STUDY OF DOUBLE PROTONS MIGRATION MECHANISM IN SUPRAMOLECULAR STRUCTURES OF ACETIC ACID-WATER AND ACETIC ACID-AMMONIA BY AB INITIO METHOD

The theoretical study of double protons migration mechanism on acetic acid-water and acetic acid-ammonia associations has been carried out. The research covered determinations the reactant, transition state and product structures. To gain the goal, the research was conducted in three steps, i.e. (i) designing the reactant, transition state and product models, (ii) optimizing of structures, and (iii) calculating of their uncorrected total energy and frequencies with ab initio methods (basis set 6-31G**). All calculations were performed using Hyperchem ver 5.0 for Windows and Gaussian 94W package program. The computational study result showed that the calculated structures were in good agreement with the hypothetical structures.   Keywords: double protons migration, acetic acid, water, ammonia, molecular mechanics and ab-initi

QSAR STUDY OF 1,10-PHENANTHROLINE DERIVATIVES AS THE ANTIMALARIAL COMPOUNDS USING ELECTRONIC DESCRIPTORS BASED ON SEMIEMPIRICAL AM1 CALCULATION

Quantitative Structure-Activity Relationship (QSAR) analysis of 1,10-phenantroline analogs as antimalarial drug has been conducted using atomic net charges (q) as predictors of their activity. Data of predictors are obtained from computational chemistry method using semi-empirical molecular orbital AM1 calculation. Antimalarial activities are taken as the activity of the drugs against plasmodium falciparum (FcM29-Cameroun) strain and are presented as the value of ln(1/IC50) where IC50 is an effective concentration inhibiting 50 % of the parasite growth.  The results show that there is correlation between antiplasmodial activity and electronic structure as represented by a linear function of activity versus atomic net charges of N1, C7, C10, C14 atoms on the 1,10-phenanthroline skeleton and is expressed by : log IC50 = -3,4398 - 14,9050 qN1 - 8,5589 qC10 - 14,7565 qC7 + 5,0457 qC11 The equation is significant at 95% level with statistical parameters : n = 13; r = 0,96275; r2 = 0,92689; SE = 0,61578 and F (4,8) = 25,3556.   Keywords: antimalarial drug; 1,10-phenanthroline; QSAR; antiplasmodial activity

KINETICS OF PALM OIL TRANSESTERIFICATION IN METHANOL WITH POTASSIUM HYDROXIDE AS A CATALYST

A study on palm oil transesterification to evaluate the effect of some parameters in the reaction on the reaction kinetics has been carried out. Transesterification was started by preparing potassium methoxide from potassium hydroxide and methanol and then mixed it with the palm oil. An aliquot was taken at certain time interval during transesterification and poured into test tube filled with distilled water to stop the reaction immediately. The oil phase that separated from the glycerol phase by centrifugation was analyzed by 1H-NMR spectrometer to determine the percentage of methyl ester conversion. Temperature and catalyst concentration were varied in order to determine the reaction rate constants, activation energies, pre-exponential factors, and effective collisions. The results showed that palm oil transesterification in methanol with 0.5 and 1 % w/w KOH/palm oil catalyst concentration appeared to follow pseudo-first order reaction. The rate constants increase with temperature. After 13 min of reaction, More methyl esters were formed using KOH 1 % than using 0.5 % w/w KOH/palm oil catalyst concentration. The activation energy (Ea) and pre-exponential factor (A) for reaction using 1 % w/w KOH was lower than those using 0.5 % w/w KOH.   Keywords: palm oil, transesterification, catalyst, first order kinetics, activation energy, pre-exponential facto

Zn-Al LAYERED DOUBLE HYDROXIDE AS HOST MATERIAL FOR SUNSCREEN COMPOUND OF p-AMINOBENZOIC ACID

Zn-Al layered double hydroxide can be used as host material for UV active compound p-aminobenzoic acid (PABA), which is having capability to block UV light of sunlight. The formation of Zn-Al-PABA was best developed in which the nucleation process was done at room temperature and followed by hydrothermal treatment at 100 oC.   To make a better product, the molar ratio of Zn to Al to PABA was adjusted to 3:1:1. From the elemental analysis and the content of PABA, it was observed that the product has structural formula of Zn0,745Al0.254(OH)1.650(PABA)0.349. 0.684H2O. The particle size of the powder as estimated using SEM was in the range 100-200 nm. FTIR and XRD proved that the p-amino benzoate ion occupied the interlayer space. This material is expected to have high sun protection factor (SPF).   Keywords: layered double hydroxide, sunscreen, p-amino benzoic acid, nanoparticl

Aplikasi Principal Component Regresion Untuk Analisis Qsar Senyawa Antioksidan Turunan Flavon/ Flavonol Menggunakan Deskriptor Elektronik Hasil Perhitungan Metode Am1

Telah dilakukan aplikasi teknik Principal Component Regresion (PCR) untuk analisis hubungan kuantitatif antara struktur elektronik dan aktivitas (QSAR) antioksidan dari senyawa turunan flavon / flavonol. Data aktivitas merupakan data sekunder yang diperoleh dari literatur dan masing-masing dinyatakan sebagai % aktivitas. Representasi struktur kimia berupa deskriptor elektronik meliputi muatan bersih atom dan momen dipol yang diperoleh dari hasil perhitungan metode semiempirik AM1. Evaluasi QSAR yang dilakuakan berupa analisis tahapan Principal Component Analysis (PCA) untuk mengkonversi variabel laten yang dilanjutkan dengan analisis regresi multilinier antara aktivitas dan variabel laten. Hasil penelitian ditunjukkan dengan model persamaan QSAR terpilih dengan menggunakan 4 komponen utama yang dipresentasikan dalam persamaan :%A = 212.2 + (7.196) T1-(20.593)T2-(192.906)T3+(242.706)T4; n=18; 2=0.822 Fhitung/Ftabel=1,397. Kata Kunci: QSAR, Principal Component Analysis, molecular modelin