Abstract

  The synthesis, characterization and spectroscopic studies of new quinazolinone substituted analogues Q1 - Q16 with analgesic activity were described. A series of novel quinazolinone derivatives were synthesized. In this view, 5-chloro anthranilic acid undergoes acetylation in the presence of acetic anhydride and anhydrous sodium acetate to give 5-chloro-N-acetyl anthranilic acid as intermediate-I which upon cyclization in the presence of phosphorous pentaoxide, glacial acetic acid and para amino benzoic acid to yield 4-[6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl] benzoic acid as intermediate-II. This resulted intermediate-II undergo mannich base reaction to produce novel quinazolinone derivatives on reaction of formaldehyde with different aromatic amines. All the synthetic derivatives were fully characterized by spectral analytical data (elemental analysis, FTIR, 1H NMR and Mass) and the purity of the compounds was determined by TLC. Analgesic activities were tested via both hot plate and acetic acid induced writhing methods. The study concluded that the compound Q5, Q8 and Q9 were found to exhibit significant analgesic activity when compared to Ibuprofen as standard drug while other derivatives exhibit moderate to good analgesic activity.

Keywords:5-Chloro Anthranilic Acid; Quinazolinone; Analgesic Activity; Ibuprofen

References

1. El-Azab Adel S., et al. “Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents”. European Journal of Medicinal Chemistry 45 (2010): 4188-4198.
2. Birhan Yihenew Simegniew., et al. “In vivo antimalarial evaluation of some 2,3-disubstituted-4(3H)-quinazolinone derivatives”. BMC Research Notes 8 (2015): 01-06.
3. Panda Sunakar and Tripathy Upendra Prasad. “Quinazoline: A molecule of significant pharmacological and biological activity”. Research Journal of Pharmacy and Technology8 (2013): 849-855.
4. Kumar Ashok., et al. “Exploration of antimicrobial and antioxidant potential of newly synthesized 2,3-disubstituted quinazoline-4(3H)-ones”. Bioorganic and Medicinal Chemistry Letters 21 (2011): 4353-4357.
5. Rhee Hee-Kyung., et al. “Synthesis and cytotoxicity of 2-phenylquinazolin-4(3H)-one derivatives”. European Journal of Medicinal Chemistry 46 (2011): 3900-3908.
6. Krishnan Suresh Kumar., et al. “Synthesis, antiviral activity and cytotoxicity evaluation of Schiff bases of some 2-phenyl quinazoline-4(3H)-ones”. European Journal of Medicinal Chemistry 45 (2010): 5474-5479.
7. Reddy PSN., et al. “Antibacterial, antifungal and antifeedant activity of quinazolinonyl-β-lactams/quinazolinones and bis (quinazolinonyl- β-lactams)”. Rasayan Journal of Chemistry04 (2010): 635-640.
8. Jatav Varsha., et al. “CNS depressant and anticonvulsant activities of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones”. European Journal of Medicinal Chemistry 43 (2007): 1945-1954.
9. Abuelizz Hatem A., et al. “Molecular docking and anticonvulsant activity of newly synthesized quinazoline derivatives”. Molecules 22 (2017): 01-13.
10. Alanazi Amer M., et al. “Synthesis, antitumor and antimicrobial activity of some new 6-methyl-3-phenyl-4(3H)-quinazolinone analogues”. Journal of Enzyme Inhibition and Medicinal Chemistry 31 (2015): 721-735.
11. Kubicova Lenka., et al. “Synthesis and biological evaluation of quinazoline-4-thiones”. Molecules 8 (2003): 756-769.
12. Tyagi Mirdula., et al. “Synthesis and blood lowering activity of some newer quinazolinones”. Indian Journal of Chemistry 41B (2002): 2367-2370.
13. Tiwary Bipransh Kumar., et al. “Implication of quinazoline-4(3H)-ones in medicinal chemistry”. Journal of Chemical Biology and Therapeutics1 (2015): 01-07.
14. Wasfy AAF., et al. “Synthesis and anticancer properties of novel quinazoline derivatives”. International Journal of Research in Pharmacy and Chemistry1 (2015): 34-40.
15. Nehal A Hamdy., et al. “Potent anti-inflammatory and analgesic activities of new derivatives of chalcone, pyridine, pyrazole and isoxazole incorporated into 5,6,7,8- tetrahydronaphthalene”. Egyptian Pharmaceutial Journal1 (2012): 22-30.
16. B Ravi Kiran., et al. “Synthesis, evaluation of analgesic and anti-inflammatory activities of substituted 1,2-Benzoxazolone and 3-Chloro-1,2-Benzoxazole derivatives”. International Journal of Pharmaceutical Science and Research7 (2015): 2918-2925.
17. Kasabe Amit J., et al. “Synthesis, anti-tubercular and analgesic activity evaluation of new 3-pyrazoline derivatives”. International Journal of Pharmacy and Pharmaceutical Sciences2 (2010): 132-135.
18. Collier HO., et al. “The abdominal constriction response and its suppression by analgesic drug in the mouse”. British Journal of Pharmacology and Chemotherapy 32 (1968): 295-310.

Citation

Citation: Ritesh Patel., et al. “Evaluation of Analgesic Activity of Some Novel Quinazolinone Analogues". Acta Scientific Medical Sciences 4.5 (2020): 89-96.

Copyright

Copyright: © 2020 Ritesh Patel., et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.