SYNTHESIS, CHARACTERIZATION AND ANTHELMINTIC ACTIVITY OF ISATIN ANALOGS AGAINST PHERITIMA POSTHUMA
bjective: Isatin (1H-indole-2,3-dione), an endogenous compound identified in many organisms, shows a wide range of biological activities. In view
of these facts, in our present communication, we wish to report the synthesis and evaluation of some isatin analogs for anthelmintic activity against
Methods: A series of 16 isatin analogs (3a-3p) have been synthesized, characterized by physical and spectral data (Fourier transform infrared,
nuclear magnetic resonance and mass) and screened for anthelmintic activity against P. posthuma at various concentrations (5, 10, and 20 mg/ml).
Results: All compounds were tested for the beginning of paralysis time followed by a time of the death of worms. All prototypes at the concentration
of 20 mg/ml showed significant activity (p<0.01) compared to that of control. The compounds 3f and 3i were found to possess significant activity
compared to standard albendazole (20 mg/ml).
Conclusion: The study encourages us to consider a new molecular skeleton of isatin substituted at the first and third position by aryl groups with
adequate spacers which may be identified as potential leads for the development of future studies in various in vivo models for anthelmintic activities.
Keywords: Isatin, Synthesis, Spectral analysis, Pheritima posthuma, Anthelmintic activity.
anthelmintic activity of some 1-substituted imidazole derivatives. Acta
Parasitol Glob 2011;2(1):1-5.
Asian J Pharm Clin Res, Vol 8, Issue 5, 2015, 162-167
Debnath and Ganguly
2. Newton SE, Munn EA. The development of vaccines against
gastrointestinal nematode parasites, particularly haemonchus contortus.
Parasitol Today 1999;15(3):116-22.
3. Bundy DA. Immunoepidemiology of intestinal helminthic infections 1.
The global burden of intestinal nematode disease. Trans R Soc Trop
Med Hyg 1994;88(3):259-61.
4. Tripathi KD. Essentials of Meditical Pharmacology. 5
ed. New Delhi:
Jaypee Brothers Medical Publishers (P) Ltd.; 2003.
5. Coles GC. Nematode control practices and anthelmintic resistance on
British sheep farms. Vet Rec 1997;141(4):91-3.
6. Geert S, Dorny P. Anthelmintic resistance in helminthes of animals of
man in the tropics. Bull Seances Acad R Sci Outre Mer 1995;3:401-23.
7. Tagbota S, Townson S. Antiparasitic properties of medicinaland other
naturally occurring products. Adv Parasitol 2001;50:199-205.
8. Sondhi SM, Shahu R, Magan A. Anthelmintic activity of Platycladus
orientalisleaves extract. Indian Drugs 1994;31(7):317-20.
9. Bennett PN, Brown MJ. Clinical Pharmacology. 19
ed. New York:
McGraw-Hill; 2000. p. 12.
10. Mesropyan EG, Avetisyan AA. New isatin derivatives. Russ J Org
11. Sumpter WC. The chemistry of isatin. Chem Rev 1994;34(3):393-34.
12. Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis antibacterial,
antifungal and anti HIV activity of Schiffâ€™s and Mannich bases of isatin
with N-[6-chlorobenz thiazole-2-yl] thiosemicarbazide. Indian J Pharm
13. 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(2):249-55.
14. Varma RS, Nobles WL. Antiviral, antibacterial, and antifungal activities
of isatin N-Mannich bases. J Pharm Sci 1975;64(5):881-2.
15. Logan JC, Fox MP, Morgan JH, Makohon AM, Pfau CJ.
Arenavirus inactivation on contact with N-substituted isatin betathiosemicarbazones
16. 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-2-methylmercapto quinazolin-4(3H)one.
17. Pandeya SN, Yogeeswari P, Sriram D, de Clercq E, Pannecouque C,
Witvrouw M. Synthesis and screening for anti-HIV activity of some
N-Mannich bases of isatin derivatives. Chemotherapy 1999;45(3):192-6.
18. Khan KM, Khan M, Ali M, Taha M, Rasheed S, Perveen S, et al.
Synthesis of bis-Schiff bases of isatins and their antiglycation activity.
Bioorg Med Chem 2009;17(22):7795-801.
19. Smitha S, Pandeya SN, Stables JP, Ganapathy S. Anticonvulsant and
sedative-hypnotic activities of N-acetyl/methyl isatin derivatives. Sci
20. Venkateshwarlu E, Rao JV, Umasankar K, Dheeraj G. Study of antiinflammatory,
J Pharm Clin Res 2012;5:187-90.
21. Chandra PM, Venkateshwar J. Biological evaluation of Schiff bases of
new isatin derivatives for anti-Alzheimerâ€™s activity. Asian J Pharm Clin
22. Matesic L, Locke JM, Bremner JB, Pyne SG, Skropeta D, Ranson M.
N-phenethyl and N-naphthylmethyl isatins and analogues as in vitro
cytotoxic agents. Bioorg Med Chem 2008;16(6):3118-24.
23. Ganguly S, Debnath B. Molecular docking studies and ADME
prediction of novel Isatin analogs with potent anti-EGFR activity. Med
24. Debnath B, Ganguly S. Molecular docking studies and ADME
prediction of novel isatin analogs as HIV-1-RT inhibitors with broad
spectrum chemo therapeutic properties. Asian J Pharm Clin Res
25. Debnath B, Ganguly S. Synthesis of some novel (2-Oxo-3-(arylimino)
indolin-1-yl)-N-aryl acetamides and evaluation as antimicrobial agents.
Toxicol Environ Chem 2015. Available from: http://www.dx.doi.org/10
26. Sridhar SK, Saravanan M, Ramesh A. Synthesis and antibacterial
screening of hydrazones, Schiff and Mannich bases of isatin derivatives.
Eur J Med Chem 2001;36(7-8):615-25.
27. Azizian J, Mohammadi MK, Firuzi O, Razzaghi-Asl N, Miri R.
Synthesis, biological activity and docking study of some new isatin
Schiff base derivatives. Med Chem Res 2012;21:3730-40.
28. Soyer Z, KiliÃ§ FS, Erol K, PabuÃ§cuoglu V. Synthesis and anticonvulsant
activity of some Ï‰-(1H-imidazol-1-yl)-N-phenylacetamide and
propionamide derivatives. Farmaco 2004;59(8):595-600.
29. Modi NR, Shah RJ, Patel MJ, Suthar M, Chauhan BF, Patel LJ. Design,
synthesis, and QSAR study of novel 2-(2, 3-dioxo-2, 3-dihydro-1Hindol-1-yl)-N-phenylacetamide
30. Akgul O, Tarikoggullari AH, Kose FA, Kirmizibayrak PB,
PabuÃ§Ã§uoglu MV. Synthesis and cytotoxic activity of some 2-(2,
3-dioxo-2, 3-dihydro-1 H-indol-1-yl) acetamide derivatives. Turk J
Chem 2013; 37(2):204-12.
31. Gbolade AA, Adeyemi AA. Anthelmintic activities of three medicinal
plants from Nigeria. Fitoterapia 2008;79(3):223-5.
32. Deore SL, Khadabadi SS, Kamdi KS, Ingle VP, Kawalkar NG,
Sawarkar PS, et al. In vitro anthelmintic activity of Cassia tora. Int J
Chem Tech Res 2009;1:177-9.
33. Ahamed SM, Kumar SV, Rao JV, Jayaveera KN, Swamy SK.
anthelmintic activity of leaves of Feronia limonia. Pharmacol Online
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