SYNTHESIS, ANALGESIC, ANTI-INFLAMMATORY AND IN VITRO ANTIMICROBIAL STUDIES OF SOME NOVEL SCHIFF AND MANNICH BASE OF 5-SUBSTITUTED ISATIN DERIVATIVES
Objective: Synthesis and analgesic, anti-inflammatory and antimicrobial evaluation of some novel Schiff and Mannich bases of isatin derivatives.
Methods: A series of novel 3-(4-(2-(substituted benzylideneamino)thiazol-4-yl)phenylimino)-1-((dimethylamino)methyl)-5-fluoroindolin-2-one Schiff and Mannich base derivatives were synthesized by using various aromatic aldehydes with isatin derivatives. The chemical structures of all synthesized compounds were confirmed by IR, 1H-NMR, Mass spectra and elemental analysis. All the synthesized compounds were screened for its analgesic, anti-inflammatory and antimicrobial activity.
Results: The results of analgesic, anti-inflammatory and antimicrobial activity showed that some of the synthesized compounds were exhibited promising results.
Conclusion: This investigation identified the potent analgesic, anti-inflammatory and anti-microbial agents and these molecules will be subjected to further studies in our laboratory.
2. Sridhar SK, Pandeya SN, Stables JP, Ramesh A. Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives. Eur J Pharm Sci 2002;16:129-32.
3. Penthala NR, Yerramreddy TR, Madadi NR, Crooks PA, Synthesis and in vitro evaluation of N-alkyl-3-hydroxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)indolin-2-one analogs as potential anticancer agents. Bioorg Med Chem Lett 2010;20:4468-71.
4. Sridhar SK, Ramesh A. Synthesis, characterization and pharmacological screening of some isatinoid compounds. Ind J Chem 2002;41B: 668-72.
5. Imam SA, Varma RS. Isatin-3-anils as excystment and cysticidal agents against Schizopyrenus russelli. Experientia 1975;31:1287-90.
6. Bhattacharya SK, Glover V, McIntyre I. Strss causes an increase in endogenous monoamine oxidase inhibitor in rat brain. Neurosci Lett 1992;92:218-20.
7. Lai Y, Mab L, Huang W, Yu X, Zhang Y, Hui J, et al. Synthesis and biological evaluation of 3-[4-(amino/methylsulfonyl) phenyl] methylene-indolin-2-one derivatives as novel COX-1/2 and 5-LOX inhibitors. Bioorg Med Chem Lett 2010;20:7349-53.
8. Chohan ZH, Pervez H, Rauf A. Isatins-derived antibacterial and antifungal compounds and their transition metal complexes. J Enz Inhi Med Chem 2004;19:417-8.
9. Pandeya SN, Smitha S, Jyoti M, Sridhar SK. Biological activities of isatin and its derivatives. Acta Pharm 2005;55:27-46.
10. Boon R. Antiviral treatment: from concept to reality. Antiviral Chem Chemother 1997;8:5-10.
11. Chiyanzu E, Hansell P, Gut J. Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain. Bioorg Med Chem Lett 2003;13:3527.
12. Iyer RA, Hanna PE, N-(Carbobenzyloxy) isatin: a slow binding Î±-keto lactam inhibitor of Î±-chymotrypsin. Bioorg Med Chem Let 1995;5:89-92.
13. Oncu S, Punar M, Erakosy H. Comparative activities of Î²-lactam antibiotics and quinolones for invasive Streptococcus pneumoniae isolates. Chemotherapy 2004;50:98-100.
14. Abedawn I, Khalaf N, Roger D, Waigh. Distamycin analogues with enhanced lipophilicity: synthesis and antimicrobial activity. J Med Chem 2004;47:2133-56.
15. Harnet JJ, Roubert V, Dolo C, Charnet C, Spinnewyn B, Cornet S, et al. Phenolic thiazoles as novel orally-active neuroprotective agents. Bioorg Med Chem Lett 2004;14:157-60.
16. Olfert ED, Cross BM, McWilliam AA. Canadian council of animal care guide to the care and use of experimental animals; 1993.
17. Kulkarni SK. Heat and other physiological stress-induced analgesia: catecholamine mediated and naloxone reversible response. Life Sci 1980;27:185-8.
18. Damour FE, Smith DL. A method for determining loss of pain sensation. J Pharmacol Exp Ther 1941;72:74-9.
19. Winter CA, Risley EA, Nuss GW. Carrageenin induced edema in hind paw of the rat as an assay for anti-inflammatory drugs. Exp Biol Med 1962;111:544-7.
20. Goyal RK, Chakrabarti A, Sanyal AK. The effect of biological variables on the anti ulcerogenic effect of vegetable plantain banana. Planta Med 1985;29:85-8.
21. Shay M, Komarov SA, Fels D, Meranze D, Grunstein H, Siplet H, A simple method for the uniform production of gastric ulceration in the rats. Gastroenterology 1945;5:43-61.
22. Ganguly AK, Bhatnagar OP. Effect of bilateral adrenalectomy on production of restraint ulcers in the stomach of albino rats. Can J Physiol Pharmacol 1973;51:748-50.
23. Hawkey PM, Lewis DA. Medical bacteriology-A practical approach. Oxford University Press: Oxford; 1994. p. 181-94.