SYNTHESIS AND EVALUATION OF ANTIMICROBIAL ACTIVITY OF QUINAZOLINONE DERIVATIVES
Keywords:Quinazolinone, Chloroacetyl chloride, Hydrazine hydrate, Microwave irradiation, Spectral studies, Antimicrobial activity
Objective: The present study aims to synthesis and evaluation of antimicrobial activity of quinazolinone derivatives.
Methods: Methyl anthranilate react with acetyl chloride in ethanol gives methyl-2 acetamido benzoate (1) which on reaction with hydrazine hydrate gives 3-amino-2 methyl 4-(3H)-quinazolinone.(2) The amino group of synthesized quinazolinone with substituted acid chloride which gives 3-Chloroacetyl amino-2-methyl-4-quinazolinone (3) which on condensation with various primary amines gives 2-(2-methyl-4-oxo-4H-quinazoline-3yl-amino)-N-substituted acetamide (4a-4j).
Results: The reaction sequence involves microwave-induced preparation of methyl-2 acetamido benzoate (1) from reaction of Methyl anthranilate react with acetyl chloride in ethanol. Further reaction with hydrazine hydrate gives 3-amino-2 methyl 4-(3H)-quinazolinone. (2) The amino group of synthesized quinazolinone with substituted acid chloride which gives 3-Chloroacetyl amino-2-methyl-4-quinazolinone (3) which on condensation with various primary amines gives 2-(2-methyl-4-oxo-4H-quinazoline-3yl-amino)-N-substituted acetamide (4a-4j).
Which were characterized by IR and 1HNMR spectral data.
Conclusion: All the synthesized compounds were screened for antimicrobial activity by Broth dilution method. Most of the derivatives showed good antimicrobial activity against Gram-Positive and Gram-negative bacteria.
2. Julio Alvarez Builla, Jose Barluenga. Heterocyclic compounds: an introduction; Modern heterocyclic chemistry. First edition; 2011. p. 1-2.
3. Shadomy S Espinel. A manual of clinical microbiology; American chemical society for microbiology: Washington DC; 1980. p. 647.
4. Stockwell C. Nature’s Pharmacy. London, O Goslinka. Antimicrobial activity of United Kingdom. Century Hutchinson Ltd; 1988.
5. Murray PR. ASM Pocket Guide to Microbiology, ASM Press: Washington DC; 1996.
6. Mohamed S Mossad, Kamel M Mohsen, Kaseem MM Emad, Nagesh Abotaleb, Nofal M Salwa, Ahmed F Marwa. Novel 6,8-dibromo-4(3H)-quinazolinone derivatives of promising anti-inflammatory and analgesic properties. Acta Poloniae Pharm Drug Res 2010;67:159-71.
7. Hosakere D, Revana Siddappa, K Shiva Prasad, L Shiva Kumar l, B Jayalakshmi. Synthesis and biologival activity of new Schiff bases containing 4 (3H)-quinazolinone ring system. Int J ChemTech Res 2010;2:1344-9.
8. Ponnilavarasan Ilangovan, Swastik Ganguly, Vijay Pandit, James P Stables. Design and synthesis of novel quinazolinone derivatives as broad spectrum anticonvulsant. Scholars Research Liabrary; DePharm Lett 2010. p. 13-21.
9. Journal of enzyme inhibition and medicinal chemistry. Res Gate 2007;220:702-8.
10. V Kasture, SK Wadodkar. Pharmaceutical analysis. Vol. II. Instrumental Methods, Nirali Prakashan; 1995. p. 267, 268, 281, 189, 308, 305, 306.
11. GR Chatwal, SK Anand. Instrumental methods of chemical analysis, Himalaya Publishing House; 1979. p. 2.599-2.616.
12. RM Silverstein, FX Webster. Spectrometric identification of organic compounds, Sixth Edition; 1963. p. 71-109.
13. Shadomy S, Espinel A. Manual of clinical microbiology; America chemical society for microbiology; Washington DC; 1980. p. 647.