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Jumina Jumina

Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta

Author-ID : 3958117

Chemical Engineering, Chemistry & Bioengineering Chemistry

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SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATION Suryadi Budi Utomo; Jumina Jumina; Dwi Siswanta; Mustofa Mustofa; Naresh Kumar
Indonesian Journal of Chemistry Vol 11, No 1 (2011)
Publisher : Universitas Gadjah Mada

A research has been conducted to synthesize thiomethylated-C-4-methoxyphenylcalix[4]resorcinarene using fennel oil as a starting material. The synthesis was carried out in four steps i.e. (1) oxidation of anethole to yield p-anisaldehyde, (2) HCl-catalyzed condensation of p-anisaldehyde with resorcinol, (3) chloromethylation of C-4-methoxyphenylcalix[4]resorcinarene with paraformaldehyde and HCl in the presence of ZnCl2 to yield tetrakis-chloromethyl-C-4-methoxyphenylcalix[4]resorcinarene, and (4) reaction of tetrakis-chloromethyl-C-4-methoxyphenylcalix[4]resorcinarene with thiourea followed by hydrolysis with sodium hydroxide solution to yield tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene. The prepared compounds were characterized based on melting point, FT-IR, and NMR spectrometers. According to the analysis of 1H-NMR spectrometer, C-4-methoxyphenylcalix[4]resorcinarene and tetrakis-chloromethyl-C-4-methoxyphenylcalix[4]resorcinarene were observed in the chair or flattened partial cone conformation, while tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene tend to exist in the crown or cone conformation.

QUANTITATIVE ELECTRONIC STRUCTURE - ACTIVITY RELATIONSHIPS ANALYSIS ANTIMUTAGENIC BENZALACETONE DERIVATIVES BY PRINCIPAL COMPONENT REGRESSION APPROACH Yuliana Yuliana; Harno Dwi Pranowo; Jumina Jumina; Iqmal Tahir
Indonesian Journal of Chemistry Vol 4, No 1 (2004)
Publisher : Universitas Gadjah Mada

Quantitative Electronic Structure Activity Relationship (QSAR) analysis of a series of benzalacetones has been investigated based on semi empirical PM3 calculation data using Principal Components Regression (PCR). Investigation has been done based on antimutagen activity from benzalacetone compounds (presented by log 1/IC50) and was studied as linear correlation with latent variables (Tx) resulted from transformation of atomic net charges using Principal Component Analysis (PCA). QSAR equation was determinated based on distribution of selected components and then was analysed with PCR. The result was described by the following QSAR equation :log 1/IC50 = 6.555 + (2.177).T1 + (2.284).T2 + (1.933).T3The equation was significant on the 95% level with statistical parameters : n = 28 r = 0.766 SE = 0.245 Fcalculation/Ftable = 3.780 and gave the PRESS result 0.002. It means that there were only a relatively few deviations between the experimental and theoretical data of antimutagenic activity. New types of benzalacetone derivative compounds were designed and their theoretical activity were predicted based on the best QSAR equation. It was found that compounds number 29, 30, 31, 32, 33, 35, 36, 37, 38, 40, 41, 42, 44, 47, 48, 49 and 50 have a relatively high antimutagenic activity.

SYNTHESIS OF 6-NITRO VERATRYL ALCOHOL AND 6-NITRO VERATRALDOXIM FROM VANILIN AS INTERMEDIATES FOR THE PREPARATION OF C-9154 ANTIBIOTIC DERVATIVES Jumina Jumina; Undri Rastuti; Sabirin Matsjeh
Indonesian Journal of Chemistry Vol 3, No 1 (2003)
Publisher : Universitas Gadjah Mada

The synthesis of 6-nitro veratryl alcohol and 6-nitro veratraldoxim from vanilin which was required as intermediates for the preparation of C-9154 antibiotic derivatives was carried out. C-9154 antibiotic is a sufficiently potent antibiotic, but so far this is produced only in low yields through microbiological processes. The reaction steps performed were (1) methylation of vanilin, (2) nitration of the methylation product, (3) reduction of the corresponding nitro compound and (4) reaction of the nitration product with HO-NH2.HCl. Methylation of vanilin was conducted using dimethylsulfate and NaOH at 60 oC for 2 hours. Nitration of the methylation product was performed in 2 methods, i.e. using neat HNO3 and using a mixture of HNO3 and H2SO4 both at 5 oC for 2 hours. Reduction of the nitration product was conducted using NaBH4 either at room temperature and at reflux. Reaction of the nitration product with HO-NH2.HCl was carried out in ethanol 95% at 50 oC for 2 hours. The products were analyzed by means of TLC, GC, IR, 1H NMR and GC-MS spectrometers. The methylation of vanilin gave 87.7% yield of veratraldehyde which was found as a white crystal (m.p 43 oC). The nitration of veratraldehyde produced 6-nitro veratraldehyde observed as a yellow crystal having of m.p. 130 oC. Nitration using neat HNO3 gave a smaller yield (50.35%) of 6-nitro veratraldehyde than nitration with a mixture of HNO3 and H2SO4 (93.63%). Reduction of 6-nitro veratraldehyde using NaBH4 at room temperature and at reflux afforded 6-nitro veratryl alcohol which was found as brown crystal (m.p 123-127 oC) respectively in 13.47% and 56.61%. This reduction also produced 6-amino veratryl alcohol and 3,4-dimethoxy benzoic zcid as by products. 6-Nitro veratraldehyde reacts with HO-NH2.HCl to give 6-nitro veratraldoxim in 48.27% yield.

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