SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SCHIFF’S AND N-MANNICH BASES OF ISATIN AND ITS DERIVATIVES WITH 4-AMINO-N-CARBAMIMIDOYL BENZENE SULFONAMIDE
Abstract
Isatin and substituted Isatin were reacted with 4-amino-N-carbamimidoyl benzene sulfonamide to form a series of Schiff’s bases. The Mannich bases of these compounds were synthesized by reacting them with formaldehyde and secondary amine (piperidine). All the compounds were characterized by means of their IR, 1H NMR spectroscopic data and elemental analysis. The antimicrobial activity of the synthesized compounds was evaluated by tube dilution method. The synthesized compounds showed better antibacterial activity than the reference drugs.
Keywords:
Isatin, Schiff’s bases, Mannich bases, Antimicrobial activityDOI
https://doi.org/10.25004/IJPSDR.2010.020214References
1. Somogyi L. Transformation of isatin 3-acylhydrazones under acetylating conditions: Synthesis and structure elucidation of 1, 5|-disubstitutedacetylspiro [oxindole-3, 2-[1, 3, 4] oxadiazolines]. Bull. Chem. Soc. Jpn. 2001; 74: 873881.
2. Pandeya SN, Sriram D. Synthesis and screening for antibacterial activity of Schiff’s and Mannich bases of Isatin and its derivatives. Acta Pharm. Turc. 1998; 40: 33-38.
3. Sarangapani M, Reddy VM. Synthesis and antimicrobial activity of 1[(N, N- disubstituted amino) methyl]-3-[(2-phenyl-3, 4-dihydro-4-oxoquinazoline-3-yl] indole-2-one. Indian J. Heterocycl. Chem. 1994; 3: 257-260.
4. Varma RS, Nobels WL. Antiviral, antibacterial and antifungal activities of isatin N-Mannich bases. J. Pharm. Sci., 1975; 64: 881-882.
5. Pandeya SN, Sriram D, Nath G, DeClercq E. Synthesis and antimicrobial activity of Schiff and Mannich bases of isatin and its derivatives with pyrimidine. Farmaco. 1999; 54: 624-628.
6. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis antibacterial, antifungal and anti HIV activity of Schiff’s and Mannich bases of isatin with N-[6-Chlorobenz thiazole-2-yl]thiosemicarbazide. Indian J. Pharm. Sci. 1999; 61: 358-361.
7. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis antibacterial, antifungal and anti HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-methylmercapto quinazolin-4(3H) one. Pharm. Acta Helv. 1999; 74: 11-17.
8. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis, antibacterial, antifungal and anti HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4-chlorophenyl) thiazol-2-yl] thiosemicarbazide. Eur. J. Pharm. Sci. 1999; 9: 25-31.
9. Pandeya SN, Yogeeswari P, Sriram D, De Clercq E, Pannecouque C, Witvrouw M. Synthesis and Screening for AntiHIV Activity of some NMannich Bases of Isatin Derivatives. Chemotherapy. 1999; 45: 192-96.
10. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis, antibacterial, antifungal and anti HIV activities of Norfloxacin Mannich bases. Eur. J. Med. Chem. 2000; 35: 249-255.
11. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis, antibacterial, antifungal and antiHIV evaluation of Schiff and Mannich bases of isatin and its derivatives with triazole. Arzneim Forsch. Drug. Res. 2000; 50: 55-59.
12. Pandeya SN, Yogeeswari P, Sriram D, Nath G. Synthesis and antimicrobial activity of N-Mannich bases of 3-[N-sulphadooximino]isatin and its methyl derivatives. Bull. Chim. Farm. 1998; 137: 321-324.
13. Ravichandran V, Mohan S, Kumar SK. Synthesis and antimicrobial activity of Mannich bases of Isatin and its derivative with 2-[(2, 6-dichlorophenyl)amino]phenylacetic acid. ARKIVOC. 2007; (xiv): 51-57.
14. Patel A, Bari S, Telele G, Patel J, Sarangapani M. Synthesis and antimicrobial activity of some new Isatin derivatives. Iran. J. Pharm. Sci. 2006; 4: 249-254.
15. Jarrahpour A, Khalili D, Clercq De E, Salmi C, Brunel M J. Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of Isatin and their derivatives. Molecules. 2007; 12: 1720-1730.
16. Bal TR, Anand B, Yogeeswari P, Sriram D. Synthesis and evaluation of anti-HIV activity of Isatin β-thiosemicarbazone derivatives. Bioorg. Med. Chem. Let. 2005; 15: 4451-4455.
17. Sriram D, Bal TR, Yogeeswari P. Aminopyrimidinoisatin anlogues: Desigen of novel non-nucleoside HIV-1 reverse transcriptase inhibitors with broad spectrum chemotherapeutic properties. J. Pharm. Pharmaceut. Sci. 2005; 8(3): 565-577.
18. Singh SP, Shukla SK, Awasthi LP. Synthesis of some 3-(4|-nitrobenzoyl-hydrzone)-2-indolinones as potential antiviral agents. Curr. Sci. 1983; 52: 766-769.
19. Selvam P, Murgesh N, Chandramohan M, Clercq De E, Keyaerts E, Vijgen L, Maes P, Neyts J, Ranst M V. In vitro antiviral activity of some novel Isatin derivative against HCV and SARS-CoV viruses. Ind. J. Pharm. Sci. 2008; 70(1): 91-94.
20. Pandeya SN, Smith S, Stable JP. Anticonvulsant and Sedativehypnotic activities of N-substituted isatin-3-semicarbazones. Arch. Pharm. 2002; 4: 129-134.
21. Verma M, Pandeya SN, Singh KN, Stables JP. Anticonvulsant activity of schiff bases of Isatin derivatives. Acta Pharm. 2004; 54: 49-56.
22. Smitha S, Pandeya SN, Stables JP, Ganpathy S. Anticonvulsant and sedative-hypnotic activities of N-acetyl/methyl Isatin derivatives. Sci. Pharm. 2008; 76: 621-636.
23. Sridhar SK, Pandeya SN, Stables JP, Ramesh A. Anticonvulsant activity of hydrazones, Schiff and Mannich bases of Isatin derivatives. Euro. J. Pharm. Sci. 2002; 16: 129-132.
24. Fadl AT, Bin-Jubair FAS. Anti-tubercular activity of Isatin derivatives. Int. J. Res. Pharm. Sci. 2010; 1(2): 113-126.
25. Hussein MA, Fadl TA, Hussein A. Synthesis and antitubercular activity of mannich bases derived from Isatin, isonicotinic acd hydrazone. Pharm Sci; Assiut University 2005; 28: 131-136.
26. Karali N, Gursoy A, Kandemirli F, Shvets N, Kaynak F B, Ozbey Suhelyla,Koalishyn V, Dimoglo A. Synthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivatives. Bioorg. Med. Chem. 2007; 15: 5888-5904.
27. Vine KL, Locke JM, Ranson M, Pyne SG, Bremner J B. In vitro cytotoxicity evaluation of some substituted Isatin derivatives. Bioorg. Med. Chem. 2007; 15: 931-938.
28. Yogeeswari P, Sriram D, Kavya R, Tiwari S. Synthesis and in vitro cytotoxicity evaluation of Gatifloxacin Mannich bases. Biomed. and pharmacother. 2005; 59: 501-510.
29. Hussain MM, Islam N Khar R, Islam Md R. Cytotoxicity study of dimethyl Isatin and its heterocyclic derivatives. Bangladesh J. Pharmacol. 2007; 2: 66-70.
30. Hawkey PM, Lewis, DA. Medical Bacteriology: A Practical Approach. Oxford University Press, Oxford. 1994, pp. 181-194.
2. Pandeya SN, Sriram D. Synthesis and screening for antibacterial activity of Schiff’s and Mannich bases of Isatin and its derivatives. Acta Pharm. Turc. 1998; 40: 33-38.
3. Sarangapani M, Reddy VM. Synthesis and antimicrobial activity of 1[(N, N- disubstituted amino) methyl]-3-[(2-phenyl-3, 4-dihydro-4-oxoquinazoline-3-yl] indole-2-one. Indian J. Heterocycl. Chem. 1994; 3: 257-260.
4. Varma RS, Nobels WL. Antiviral, antibacterial and antifungal activities of isatin N-Mannich bases. J. Pharm. Sci., 1975; 64: 881-882.
5. Pandeya SN, Sriram D, Nath G, DeClercq E. Synthesis and antimicrobial activity of Schiff and Mannich bases of isatin and its derivatives with pyrimidine. Farmaco. 1999; 54: 624-628.
6. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis antibacterial, antifungal and anti HIV activity of Schiff’s and Mannich bases of isatin with N-[6-Chlorobenz thiazole-2-yl]thiosemicarbazide. Indian J. Pharm. Sci. 1999; 61: 358-361.
7. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis antibacterial, antifungal and anti HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-methylmercapto quinazolin-4(3H) one. Pharm. Acta Helv. 1999; 74: 11-17.
8. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis, antibacterial, antifungal and anti HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4-chlorophenyl) thiazol-2-yl] thiosemicarbazide. Eur. J. Pharm. Sci. 1999; 9: 25-31.
9. Pandeya SN, Yogeeswari P, Sriram D, De Clercq E, Pannecouque C, Witvrouw M. Synthesis and Screening for AntiHIV Activity of some NMannich Bases of Isatin Derivatives. Chemotherapy. 1999; 45: 192-96.
10. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis, antibacterial, antifungal and anti HIV activities of Norfloxacin Mannich bases. Eur. J. Med. Chem. 2000; 35: 249-255.
11. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis, antibacterial, antifungal and antiHIV evaluation of Schiff and Mannich bases of isatin and its derivatives with triazole. Arzneim Forsch. Drug. Res. 2000; 50: 55-59.
12. Pandeya SN, Yogeeswari P, Sriram D, Nath G. Synthesis and antimicrobial activity of N-Mannich bases of 3-[N-sulphadooximino]isatin and its methyl derivatives. Bull. Chim. Farm. 1998; 137: 321-324.
13. Ravichandran V, Mohan S, Kumar SK. Synthesis and antimicrobial activity of Mannich bases of Isatin and its derivative with 2-[(2, 6-dichlorophenyl)amino]phenylacetic acid. ARKIVOC. 2007; (xiv): 51-57.
14. Patel A, Bari S, Telele G, Patel J, Sarangapani M. Synthesis and antimicrobial activity of some new Isatin derivatives. Iran. J. Pharm. Sci. 2006; 4: 249-254.
15. Jarrahpour A, Khalili D, Clercq De E, Salmi C, Brunel M J. Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of Isatin and their derivatives. Molecules. 2007; 12: 1720-1730.
16. Bal TR, Anand B, Yogeeswari P, Sriram D. Synthesis and evaluation of anti-HIV activity of Isatin β-thiosemicarbazone derivatives. Bioorg. Med. Chem. Let. 2005; 15: 4451-4455.
17. Sriram D, Bal TR, Yogeeswari P. Aminopyrimidinoisatin anlogues: Desigen of novel non-nucleoside HIV-1 reverse transcriptase inhibitors with broad spectrum chemotherapeutic properties. J. Pharm. Pharmaceut. Sci. 2005; 8(3): 565-577.
18. Singh SP, Shukla SK, Awasthi LP. Synthesis of some 3-(4|-nitrobenzoyl-hydrzone)-2-indolinones as potential antiviral agents. Curr. Sci. 1983; 52: 766-769.
19. Selvam P, Murgesh N, Chandramohan M, Clercq De E, Keyaerts E, Vijgen L, Maes P, Neyts J, Ranst M V. In vitro antiviral activity of some novel Isatin derivative against HCV and SARS-CoV viruses. Ind. J. Pharm. Sci. 2008; 70(1): 91-94.
20. Pandeya SN, Smith S, Stable JP. Anticonvulsant and Sedativehypnotic activities of N-substituted isatin-3-semicarbazones. Arch. Pharm. 2002; 4: 129-134.
21. Verma M, Pandeya SN, Singh KN, Stables JP. Anticonvulsant activity of schiff bases of Isatin derivatives. Acta Pharm. 2004; 54: 49-56.
22. Smitha S, Pandeya SN, Stables JP, Ganpathy S. Anticonvulsant and sedative-hypnotic activities of N-acetyl/methyl Isatin derivatives. Sci. Pharm. 2008; 76: 621-636.
23. Sridhar SK, Pandeya SN, Stables JP, Ramesh A. Anticonvulsant activity of hydrazones, Schiff and Mannich bases of Isatin derivatives. Euro. J. Pharm. Sci. 2002; 16: 129-132.
24. Fadl AT, Bin-Jubair FAS. Anti-tubercular activity of Isatin derivatives. Int. J. Res. Pharm. Sci. 2010; 1(2): 113-126.
25. Hussein MA, Fadl TA, Hussein A. Synthesis and antitubercular activity of mannich bases derived from Isatin, isonicotinic acd hydrazone. Pharm Sci; Assiut University 2005; 28: 131-136.
26. Karali N, Gursoy A, Kandemirli F, Shvets N, Kaynak F B, Ozbey Suhelyla,Koalishyn V, Dimoglo A. Synthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivatives. Bioorg. Med. Chem. 2007; 15: 5888-5904.
27. Vine KL, Locke JM, Ranson M, Pyne SG, Bremner J B. In vitro cytotoxicity evaluation of some substituted Isatin derivatives. Bioorg. Med. Chem. 2007; 15: 931-938.
28. Yogeeswari P, Sriram D, Kavya R, Tiwari S. Synthesis and in vitro cytotoxicity evaluation of Gatifloxacin Mannich bases. Biomed. and pharmacother. 2005; 59: 501-510.
29. Hussain MM, Islam N Khar R, Islam Md R. Cytotoxicity study of dimethyl Isatin and its heterocyclic derivatives. Bangladesh J. Pharmacol. 2007; 2: 66-70.
30. Hawkey PM, Lewis, DA. Medical Bacteriology: A Practical Approach. Oxford University Press, Oxford. 1994, pp. 181-194.
Published
01-04-2010
Statistics
Abstract Display: 831 
PDF Downloads: 673
Dimension Badge
How to Cite
“SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SCHIFF’S AND N-MANNICH BASES OF ISATIN AND ITS DERIVATIVES WITH 4-AMINO-N-CARBAMIMIDOYL BENZENE SULFONAMIDE”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 2, no. 2, Apr. 2010, pp. 151-4, https://doi.org/10.25004/IJPSDR.2010.020214.
Issue
Section
Research Article
Copyright (c) 2010 U. K. Singh, S. N. Pandeya, A. Singh, B. K. Srivastava, M. Pandey
This work is licensed under a Creative Commons Attribution 4.0 International License.
How to Cite
“SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SCHIFF’S AND N-MANNICH BASES OF ISATIN AND ITS DERIVATIVES WITH 4-AMINO-N-CARBAMIMIDOYL BENZENE SULFONAMIDE”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 2, no. 2, Apr. 2010, pp. 151-4, https://doi.org/10.25004/IJPSDR.2010.020214.
