Sintesis senyawa antimalaria (1)-N-3',4'-Dimetoksibenzil-1,10-Fenantrolinium Klorida dan (1)-N-3',4'-Dimetoksibenzil-1,10-Fenantrolinium Bromida dari Vanilin

JULIANTO, Tatang Shabur, Dr. H. Chairil Anwar

2007 | Tesis | S2 Ilmu Kimia

Malaria merupakan salah satu penyakit utama yang menyebabkan kematian di negara-negara tropis. Usaha pemberantasan malaria telah dilakukan, namun hingga saat ini belum memberikan hasil yang optimal. Hal ini disebabkan oleh resistensi parasit Plasmodium terhadap antimalaria utama kloroquin. Penelitian sintesis senyawa antimalaria telah banyak dilakukan, salah satunya adalah sintesis turunan 1,10-fenantrolin. Dalam penelitian ini dilakukan sintesis turunan 1,10- fenantrolin lainnya dengan menggunakan bahan dasar vanilin. Mula-mula dilakukan sintesis 3,4-dimetoksibenzaldehida melalui metilasi vanillin menggunakan dimetil sulfat. Selanjutnya dilakukan reduksi 3,4- dimetoksibenzaldehida pada temperatur kamar menggunakan reduktor NaBH4 dalam pelarut metanol membentuk 3,4-dimetoksibenzil alkohol. Produk yang diperoleh selanjutnya dihalogenasi. Reaksi halogenasi yang pertama menggunakan SOCl2 pada temperatur refluks dalam pelarut diklorometana selama 18 jam membentuk 3,4-dimetoksibenzil klorida. Reaksi halogenasi kedua menggunakan PBr3 pada temperatur refluks dalam pelarut diklorometana selama 4 jam membentuk 3,4- dimetoksibenzil bromida. Selanjutnya 3,4-dimetoksibenzil klorida dan 3,4- dimetoksibenzil bromida masing-masing direaksikan dengan 1,10-fenantrolin monohidrat dalam pelarut aseton dan direfluks selama 11 jam membentuk senyawa (1)-N-3',4'-dimetoksibenzil-1,10-fenantrolinium klorida dan (1)-N-3',4'- dimetoksibenzil-1,10-fenantrolinium bromida. Identifikasi produk dilakukan dengan Kromatografi Lapis Tipis (KLT), spektrofotometer inframerah (IR), spektrometer proton resonansi magnetik inti (1H-NMR) dan spektrometer massa (MS). Pada penelitian ini diperoleh senyawa (1)-N-3',4'-dimetoksibenzil-1,10- fenantrolinium klorida dan (1)-N-3',4'-dimetoksibenzil-1,10-fenantrolinium bromida berturut-turut dengan rendemen 57,40 % dan 59,19 %.

Malaria is one of the major disease causing death in tropical countries. Attempts to eradicate malaria have been done, but it has not given optimal results. It is caused by the resistance of Plasmodium parasite to the main antimalarial drug of chloroquine. Many researches in the synthesis of antimalarial compounds have been conducted, one of them is 1,10-phenanthroline derivative. In this research, it was synthesized other 1,10-phenanthroline derivatives from vanillin. Firstly, it was done the synthesis of 3,4-dimethoxybenzaldehyde through methylation of vanillin with dimethyl sulphate. Furthermore, it was conducted reduction of 3,4-dimethoxybenzaldehyde using NaBH4 in methanol to give 3,4- dimethoxybenzyl alcohol. The product was then halogenated. The first halogenation was carried out using SOCl2 in dichloromethane at reflux for 18 hours to give 3,4- dimethoxybenzyl chloride. The second halogenation was carried out using PBr3 in dichloromethane at reflux for 4 hours to afford 3,4-dimethoxybenzyl bromide. Each product was reacted with 1,10-phenanthroline in acetone at reflux for 11 hours to give (1)-N-3',4'-dimethoxybenzyl-1,10-phenanthrolinium chloride and (1)-N-3',4'- dimethoxybenzyl-1,10-phenanthrolinium bromide, respectively. Identification of the products was carried out by means of infrared (IR) spectrophotometer, proton nuclear magnetic resonance (1H-NMR) spectrometer, and mass spectrometer (MS). Within this research, (1)-N-3',4'-dimethoxybenzyl-1,10-phenanthrolinium chloride and (1)-N-3',4'-dimethoxybenzyl-1,10-phenanthrolinium bromide were obtained in 57.40 % and 59.19 % yield, respectively

Kata Kunci : Antimalaria,Sintesis Turunan 1,10 Fenantrolinium,antimalarial compound