07-11-2012, 01:49 PM
SYNTHESIS OF BIOACTIVE 3,4,5-SUBSTITUTED FURAN-2(5H)-ONES
[attachment=38407]
INTRODUCTION:
With every possible bacterial infection,resistance to antibiotic treatment is a common phenomenon.Hence the research still on anti – microbial agents is continuously going on to develop novel molecules.
Recently, heterocyclic compounds and their derivatives have attracted strong interest in medicinal chemistry due to their biological and pharmacological properties.
Furanones are heterocyclic compounds containing oxygen
atom in their ring structure, having various pharmacological activities like antimicrobial,antiinflammatory,anticancer and antiviral activities.
OBJECTIVE:
A large number of medicinal compounds , which have been discovered, belong to a major class of heterocycles. The versatile synthetic applicability & biological activity of these heterocycles has helped the medicinal chemist to plan ,organise & implement new approaches towards discovery of novel drugs.
Literature survey reveals that furanone & 2-amino-4-phenyl thiazole having heterocyclic moeity have attracted considerable attention as they are endowed with a wide range of diverse biological activities .
In the light of these findings it was a clear oppurtunity to combine both the ring systems to introduce an additional landmark for chemical diversities & thus enable exploration of novel pharmacophore with potential antimicrobial activity.
Hence the main objective of the present project are:
Synthesis of some new hybrid compounds containing furanone & 2-aminophenyl thiazole moiety.
Characterisation of newly synthesized compounds through NMR & mass spectral studies.
Evaluation of newer derivatives for their antimicrobial activity.
PROCEDURE:
DABCO( 0.1 mmol (10 mol %)) was dissolved in
Acetonitrile . To this clear solution, aminothiazole (1.0 mmol) was
added and stirred for 2 min, and then diethylacetylenedicarboxylate
( 1.0 mmol) followed by benzaldehyde ( 1.0 mmol)
were added, after which the reaction mixture was heated at 50–
55C until completion of the reaction as indicated by TLC. The reaction mixture was cooled to the room temperature and b-CD was filtered, the aqueous phase was extracted with ethyl acetate. The organic layers were washed with water, saturated brine solution and dried over anhydrous Na2SO4. The combined organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate and hexane as eluent to give the compound
[attachment=38407]
INTRODUCTION:
With every possible bacterial infection,resistance to antibiotic treatment is a common phenomenon.Hence the research still on anti – microbial agents is continuously going on to develop novel molecules.
Recently, heterocyclic compounds and their derivatives have attracted strong interest in medicinal chemistry due to their biological and pharmacological properties.
Furanones are heterocyclic compounds containing oxygen
atom in their ring structure, having various pharmacological activities like antimicrobial,antiinflammatory,anticancer and antiviral activities.
OBJECTIVE:
A large number of medicinal compounds , which have been discovered, belong to a major class of heterocycles. The versatile synthetic applicability & biological activity of these heterocycles has helped the medicinal chemist to plan ,organise & implement new approaches towards discovery of novel drugs.
Literature survey reveals that furanone & 2-amino-4-phenyl thiazole having heterocyclic moeity have attracted considerable attention as they are endowed with a wide range of diverse biological activities .
In the light of these findings it was a clear oppurtunity to combine both the ring systems to introduce an additional landmark for chemical diversities & thus enable exploration of novel pharmacophore with potential antimicrobial activity.
Hence the main objective of the present project are:
Synthesis of some new hybrid compounds containing furanone & 2-aminophenyl thiazole moiety.
Characterisation of newly synthesized compounds through NMR & mass spectral studies.
Evaluation of newer derivatives for their antimicrobial activity.
PROCEDURE:
DABCO( 0.1 mmol (10 mol %)) was dissolved in
Acetonitrile . To this clear solution, aminothiazole (1.0 mmol) was
added and stirred for 2 min, and then diethylacetylenedicarboxylate
( 1.0 mmol) followed by benzaldehyde ( 1.0 mmol)
were added, after which the reaction mixture was heated at 50–
55C until completion of the reaction as indicated by TLC. The reaction mixture was cooled to the room temperature and b-CD was filtered, the aqueous phase was extracted with ethyl acetate. The organic layers were washed with water, saturated brine solution and dried over anhydrous Na2SO4. The combined organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate and hexane as eluent to give the compound