Synthesis and Characterization of some new 2-Methyl-3-N-Substituted Imino - 5, 6-Tetramethylene Thieno [2, 3-D]-Pyrimidin (3h)–4-ones for Anti-bacterial and Antifungal screening
Hygeia.J.D.Med.7 (1) April 2015; 38-45
S. Ramamurthy1, E.Jayachandran2
1. Department of Pharmaceutical Chemistry, V.V.Pura institute Pharmaceutical Sciences, B.S.K IIStage, Bangalore, Karnataka, India.
2. Department of Pharmaceutical Chemistry, S.C.S.College of Pharmacy, Harapanahalli, Karnataka,India.
Plan:To synthesize some Schiff bases of 2-Methyl-3-N-amino-5,6-disubtituted thieno [2, 3-d] - pyrimidin (3H)-4-ones for antibacterial and antifungal activities.
Preface: Organiccompounds containing thiophene and pyrimidine form a significant group of drugsand known forpharmacological activities having various therapeutic applications. Thecompounds containing Thieno(2,3-b) pyrimidine nucleusposses broad range of pharmacological activities namely antibacterial,antifungal, trichomicidal, anti-malarial,anti-inflammatory activity ,etc.Thus a new series of Thieno[2,3-d]-pyrimidinones have been synthesized by reacting the active 3-aminogroup with various substituted aryl aldehydes and screened for antibacterialand antifungal activity.
Methodology: In our present investigation we have prepared theintermediate S-2 starting fromcyclohexanone and ethyl cyano acetate, involving the elegant method describedby Gewald et.al. This compound S-2 wastreated with acetic anhydride followed by hydrazine hydrate to yield the parentcompound RJ-2.This compound wasderivatized to various Schiff bases by treating with various substituted arylaldehydes. The synthesized title compounds were characterized by MP, TLC, UVand afew representative compounds by IR, NMR & Massspectrum. The compounds were screened for antibacterial and antifungalactivity.
Outcome : The new title compounds possessing ‘electron withdrawing groups’ on the aldehydic phenylring (RJ-2d, RJ-2j, RJ-2f, RJ-2l) exhibited better antibacterial and antifungal activity compared to thecompounds possessing ‘electron donating groups’(RJ-2e, RJ-2k, RJ-2m)
Keywords: Thieno [2,3-d]-pyrimidin (3H)-4-one, Schiff bases, Characterization, Antibacterial activity Antifungal activity.
S. Ramamurthy, E. Jayachandran. Synthesis and characterization of some new2-methyl-3-n-substituted imino - 5, 6-tetramethylene thieno [2, 3-d]-pyrimidin(3h)–4-ones for anti-bacterial and antifungal screening.Hygeia.J.D.Med.7(1) April 2015; 38-45. Available from http://www.hygeiajournal.com
Scheme of synthesis.