Preparation of some heterocyclic compounds (Six-membered ring)derived from Sulfadiazine drug and evaluation of their biological activity

Abstract

This study included synthesis and characterization of some heterocyclic compounds (Six-membered ring),according to the following steps: 1- Preparation of Imine compounds [ A1- A10] by the reaction of the amine (sulfadiazine) with substituted benzaldehyde using methanol as a solvent and 3drops of glacial acetic acid as a catalyst. 2- Preparation of the heterocyclic compounds (Six-membered ring) by using two methods as a following: - A- Tetrahydroquinoline compounds ( B11-B20):- They were prepared through Imino -Diels -Alder Reaction by use the derivative of Schiff bases ( A1 -A10 ) with cinnamic acid where The gave compound( B11 , B12 , B14 , B15 , B18 , B19) and cinnamaldehyde given (B13 , B16 , B17 , B20 ), and use Toluene as a solvent and Boron trifluoride diethyl etherate (BF3.Et2O) as a catalyst.(scheme 1 ) B- Quinazolin compounds (C21 –C30):- The were Prepared by reacting three components in one container of carboxylic acid anhydride ( isatoic anhydride) primary amine )sulfadiazine( and substituted benzaldehyde with tetrahydrofuran as a non-protic solvent and the acidic sodium bisulfate(NaHSO4) as a catalyst. . (scheme 1) 3- All reactions were monitored by thin layer chromatography (TLC) , Technology and determination of Retention factor ( Rf ) for all compound. 4- Characterization of all the compounds prepared with the infrared (FT-IR) spectra, and the nuclear magnetic resonance ( 1H-NMR) spectra for compounds ( B11 , B12 , B13 , B16 , B19 , B20 , C21 , C22 ,C28), and the ( 13C-NMR) spectra for compounds( B11 ,B13 ,C21 ,C30 ). 5- Evaluation of the biological effectiveness of some prepared compounds against the growth of the following bacteria: - A- Bacteria a Gram-Negative (Escherichia coli , Pseudomonas aeruginosa). B- Bacteria a Gram-Positive (Staphylococcus aureus, Streptococcus pyogenes). 6- Evaluation of the biological effectiveness of some prepared compounds against the growth of the following Anti-fungi :-( Aspergillus niger , Candida )