Biological activities of isatin and its derivatives

Acta Pharmaceutica

Volumn 55, Issue 1, 2005, Pages 27-46

  Pandeya, Surendra Nath ^a   Smitha, Sivakumar ^b   Jyoti, Mayank ^b   Sridhar, Seshaiah Krishnan ^c  

^a BANARAS HINDU UNIVERSITY   (India)

^b SAM HIGGINBOTTOM UNIVERSITY OF AGRICULTURE   (India)

^c C L BAID METHA COLLEGE OF PHARMACY   (India)

Author keywords

Anticonvulsant; Antimicrobial; Antitubercular effects; Isatin; Mannich bases; Semicarbazones

Indexed keywords

7 NITROINDAZOLE; ANTIALLERGIC AGENT; ANTICOAGULANT AGENT; ATRIAL NATRIURETIC FACTOR RECEPTOR; FIBRINOLYTIC AGENT; HYDRAZONE DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; INDOLE DERIVATIVE; INDOLINONE DERIVATIVE; ISATIN; ISATIN (3 O NITROPHENYL)HYDRAZONE; ISATIN 3 THIOSEMICARBAZONE DERIVATIVE; ISATIN DERIVATIVE; MANNICH BASE; METISAZONE; MORPHOLINE DERIVATIVE; MUSCLE RELAXANT AGENT; N DIMETHYL 5 METHYLISATIN; SEMICARBAZONE DERIVATIVE; TRIMETHOPRIM; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTICONVULSANT ACTIVITY; ANTIDIURESIS; ANTIVIRAL ACTIVITY; ANXIETY; DRUG ACTIVITY; DRUG EFFICACY; DRUG POTENCY; FROG; HEART PROTECTION; HUMAN; HYPOTENSION; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; RESPIRATION DEPRESSION; REVIEW; SEDATION; SMALLPOX VIRUS; STRUCTURE ACTIVITY RELATION; VACCINIA VIRUS;

EID: 17644424572     PISSN: 13300075     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (66)

1. V. Glover, J. M. Halket, P. J. Watkins, A. Clow, B. L. Goddwin and M. J. Sandier, Isatin-identity with the purified endogenous monoamine oxidase inhibitor tribulin, Neurochemistry 51 (1988) 656-659.
2. J. Seidel and J. Wenzel, Some histochemical and electrophysiological effects of isatin, Pol. J. Pharmacol. 35 (1979) 407-410.
3. I. M. Mc Intyre and T. R. Norman, Seratonergic effects of isatin: An endogenous MAO inhibitor related to tribulin, J. Neural Transm. 79 (1990) 35-40.
4. S. K. Bhattacharya and A. Chakraborti, Dose related proconvulsant and anticonvulsant activity of isatin, a putative biological factor in rats, Indian. J. Exp. Biol. 36 (1998) 118-121.
5. S. K. Bhattacharya, Anticonvulsant activity of intraventricularly administered atrial natriuretic peptide and its nhibition by isatin, Biog. Amines 14 (1988) 131-141.
6. F. Li, W. Yue, M. Minanii, J. Zhang and Z. Liu, Inhibitory effect of isatin on amigdaloid kindling seizure in rats, Yaoxue Xuebao 34 (1999) 1-4; ref. Chem. Abstr. 131 (1991) 82850n.
7. F. Li, W. Yue, M. Minanii, J. Zhang and Z. Liu, Inhibitory effect of isatin on amigdaloid kindling seizure in rats, Yaoxue Xuebao 34 (1999) 1-4; ref. Chem. Abstr. 131 (1991) 82850n.
8. H. Pajouhesh, R. Parson and F. D. Popp, Potential anticonvulsants VI: Condensation of isatin with cyclohexanone and other cyclic ketones, J. Pharm. Sci. 72 (1983) 318-321.
9. R. Jain and Bansal, A facile synthesis and central nervous system activities of fluorine-containing spiro 3H-indole-3,4(4H)-pyran)-2(1H)ones, Pharmazie 50 (1995) 224-225.
10. T. Blackburn, K. Paul and G. Smith, Medicaments for Treatment of Migraine, Epilepsy and Feeding Disorders, G.B. Pat. 9,425,012, 28 Apr 1993; ref. Chem. Abstr. 122 (1995) 72046e.
11. R. Di Fabio, A. M. Capelli, N. Conti, A. Cugola, D. Donati, A. Feriani, G. Gastaldi, G. Gaviraghi, C. T. Hewkin, F. Micheli, A. Missio, M. Mugnaini, A. Pecunioso, A. M. Quaglia, E. Ratti, L. Rossi, G. Tedesco, D. G. Trist and A. Reggiani, Substituted indole-2-carboxylates as in vivo potent antagonists acting at the strychnine-insensitive glycine binding site, J. Med. Chem. 40 (1997) 841-850.
12. H. P. Olesen and A. Kanstrup, Preparation of Pyrido [2,3-b] Indoles for Treating a Disease in the CNS via the Metabotropic Glutamate Receptor System, Den. Pat. 97,05,137, 13 Feb 1997; ref. Chem. Abstr. 126 (1997) 212050m.
13. O. A. Sharaf, Some pharmacological activities of new substituted pyrollo indoles, indolothiazepine and azole derivatives, Bull. Fac. Pharm. 35 (1997) 79-82.
14. Y. Evanno, M. Sevrin, C. Maloizel, O. Legalbudec and P. George, Preparation of 1H-pyrido [3,4-b] Indole-4-Carboxamide Derivatives, Fr. Pat. 9,815,552, 16 Apr 1998; ref. Chem. Abstr. 128 (1998) 282832h.
15. K. P. Jakobsen, F. P. Anders, H. P. Olesan, B. Lundbech and M. Jane, Preparation of Thieno [2,3-b] Indoles and Pyrido [2,3-b] Indoles as Antagonist at the Metabotropic Glutamate Receptor, U.S. Pat. 5,783,575, 21 Jul 1998; ref. Chem. Abstr. 129 (1998) 148909f.
16. Y. Evanno, L. Dubois, M. Sevrin, F. Marguet, J. Proissant, R. Bartsch and C. Gille, 4-Oxo-3,5-dihydro-4H-pyridazano-4,5-b-indole-1-acetamide Derivatives, Their Preparation and their Application in Therapy as GABA Agonists, Fr. Pat. 9,906,406,11 Feb 1999; ref. Chem. Abstr. 130 (1999) 168385f.
17. N. Karali and A. Gursoy, Synthesis and anticonvulsant activity of some new thiosemicarbazone and 4-thiazolidine derivatives bearing an isatin moiety, Farmaco 49 (1994) 819-822.
18. N. Karali, G. Capan and C. N. Ergen, Synthesis, characterisation and preliminary anticonvulsant evaluation of new indoline 2,3-dione derivatives, Sci. Pharm. 65 (1997) 277-287.
19. N. L. Reddy, M. Maillard, D. Berlove, M. David, D. Sharad and J. Graham, Indolinyl and Tetrahydro Quinolyl Carboxamidines with Anticonvulsant Activity, U.S. Pat. 9,730,054, 21 Aug 1997; ref. Chem. Abstr. 127 (1997) 234258h.
20. A. Gursoy and N. Karali, Some 3-hydrazono-2-indolinones and N-Mannich bases as potential anticonvulsants, Farmaco 51 (1996) 437-442.
21. F. D. Popp and B. E. Donigan, Synthesis of 3-hydroxy-3-phenacyloxindole analogs, J. Pharm. Sci. 68 (1979) 519-520.
22. G. Galambos, B. Kiss and E. Palosi, Process for Producing Spiro-oxindole Derivatives and Pharmaceutical Preparations Containing them for Treatment of Hypoxia, Convulsions and Brain Oedema, Hun. Pat. 65,452, 28 Jun 1994; ref. Chem. Abstr. 123 (1995) 169529y.
23. A. Ghaney and A. El-Helby, Synthesis and anticonvulsant activity of some substituted-1H-isoindole-1,3-d:ones, J. Pharm. Sci. 36 (1996) 343-352.
24. C. David, T. Marie and G. Roussel, Preparation, resolution and cyclisation of 2-{1-[(7-Cl-1,8-napthyridine-2-yl-amino 6-methyl-3-oxoheptyl} benzoic add to 2-isoindolinyl napthyridine, U.S. Pat. 5,498,716, 12 Mar 1996; ref. Chem. Abstr. 124 (1996) 343271r.
25. S. E. Smith, C. M. Man, P. K. Yip, E. Jang, A. G. Chapman and B. S. Meldrum, Anticonvulsant effects of 7-nitroindazole in rodents with reflex epilepsy may result from L-arginine accumulation or a reduction of nitric oxide, Br J. Pharmacol. 119 (1996) 165-173.
26. J. A. Alabadi, J. L. Thibault, E. Pinard, J. Seylaz and F. Lasbennes, 7-Nitro indazole, a selective inhibitor of nNos, increases hippocampal extracellular glutamate concentration in status epilepticus induced by kainic acid in rats, Brain Res. 839 (1999) 305-312.
27. S. K. Srivastava, S. Srivastava and S. D. Srivastava, Synthesis of new carbazolyl-thiadiazolyl-2-oxa-azetidines, antimicrobial, anticonvulsant and anti-inflammatory agents, Indian J. Chem. 38B (1999) 183-187.
28. G. S. Singh, T. Singh and R. Lakhan, Synthesis, C-13 NMR and anticonvulsant activity of new isatin based spiroazetidinones, Indian J. Chem. 36B (1997) 951-954.
29. S. N. Pandeya, I. Ponnilavarasan, A. Pandey, R. Lakhan and J. P. Stables, Evaluation of p-nitrophenyl substituted semicarbazones for anticonvulsant properties, Pharmazie 54 (1999) 12-16.
30. S. N. Pandeya, S. Smitha and J. P. Stables, Anticonvulsant and sedative-hypnotic activities of N-substituted isatin semicarbazones, Arch. Pharm. Pharm. Med. Chem. 4 (2002) 129-134.
31. S. N. Pandeya, A. Senthil Raja and J. P. Stables, Synthesis of isatin semicarbazones as novel anticonvulsants - role of hydrogen bonding, J. Pharm. Pharm. Sci. 5 (2002) 266-271.
32. S. N. Pandeya, A. K. Agarwal, A. Singh and J. P. Stables, Design and synthesis of semicarbazones and their bio-isosteric analogues as potent anticonvulsant. The role of hydrogen bonding, Acta Pharm. 53 (2003) 15-24.
33. M. Verma, S. N. Pandeya, K. Singh and J. P. Stables, Anticonvulsant activity of Schiff bases of isatin derivatives, Acta Pharm. 54 (2004) 49-56.
34. G. Palit, R. Kumar, G. K. Patnaik and S. K. Bhattacharya, Behavioral effects of isatin, a putative biological factor, in rhesus monkeys, Biogenic Amines 13 (1997) 131-142.
35. A. E. Medvedev, A. Goodwin, A. Clow, J. Halket, V. Glover and M. Sandler, Inhibitory potency of some isatin analogues on human monoamine oxidase A and B, Biochem. Pharmacol. 44 (1992) 590-592.
36. N. Hamaue, N. Yamazaki, M. Minami, T. Endo, M. Hirafugi, Y. Monma, H. Jogashi, H. Saito and S. H. Parvez, Effect of isatin, an endogenous MAO inhibition on acetylcholine and dopamine levels in the rat striatum, Biogenic Amines 15 (1999) 367-377.
37. Y. Tozawa and A. Veki, Stress induced increase in urinary excretion in rats reversal by both dexamethasone and α-methyl-p-tyrosine, Biochem. Pharmacol. 56 (1998) 1041-1046.
38. M. Sarangapani and V. M. Reddy, Pharmacological screening of isatin-[N-(2-alkyl benzoxazole-5-carbonyl) hydrazones, Indian. J. Pharm. Sci. 59 (1997) 105-109.
39. L. Kennis, M. J. Edmund and C. Josephus, Hexahydro pyrido (4,3-b) indole derivatives as antipsychotic drugs, Bel. Pat. 9,744,040, 27 Nov 1997; ref. Chem. Abstr. 28 (1998) 34772e.
40. R. S. Varma and W. L. Nobles, Substituted N-amino methyl isatins, J. Med. Chem. 10 (1967) 510-513.
41. M. Kupinić, M. Medić-Šarić, M. Movrin and D. Maysinger, Antibacterial and antifungal activities of isatin N-Mannich bases, J. Pharm. Sci. 68 (1979) 459-462.
42. D. Maysinger, J. Ban and M. Movrin, Effects of isatin N-Mannich bases on HeLa cells, Arzneim. Forsch. 30 (1980) 932-935.
43. R. W. Daisley and V. K. Shah, Synthesis and antibacterial activity of some-5-nitro-3-phenyl imino indole-2-(3H)-ones and their N-Mannich bases, J. Pharm. Sci. 73 (1984) 407-411.
44. S. Dilber, M. Saban, A. Gelinco, L. Arsenijević, M. Bogavac and S. Pavlov, Investigation of antimicrobial activity of some isatin derivatives-II, Pharmazie 45 (1990) 800-805.
45. S. N. Pandeya and D. Sriram, Synthesis and screening of antibacterial activity of Schiff and Mannich bases of isatin derivatives, Acta. Pharm. Turc. 40 (1998) 33-36.
46. S. N. Pandeya, P. Yogeeswari, D. Sriram and G. Nath, Synthesis and antimicrobial activity of N-Mannich bases of 3-[N′-sulphadoximino] isatin and its methyl derivative, Boll. Chim. Farm. 137 (1998) 321-324.
47. S. N. Pandeya, C. Gnana Sundari, M. Mariammal, M. Saravanan, P. Saravana Balaji, S. Senthil Kumar and D. Sriram, Synthesis and antibacterial activity of Mannich bases of ciprofloxacin and lomefloxacin with isatin and its derivatives, Indian J. Pharm. Sci. 60 (1998) 280-282.
48. S. N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Synthesis, antibacterial antifungal and anti-HIV activities of Schiff and Mannich bases derivatives from isatin derivatives and N-[4-(4′-chlorophenyl) thiazol-2-yl] thiosemicarbazides, Eur. J. Pharm. Sci. 9 (1999) 25-31.
49. S. N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Synthesis, antibacterial, antifungal and anti-HIV activity of Schiff and Mannich bases of isatin with N-[6-chlorobenzthiazol-2-yl] thiosemicarbazide, Indian J. Pharm. Sci. 61 (1999) 358-361.
50. S. N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivative with 3-amino-2-methyl-mercapto quinazolin-4(3H)-one, Pharm. Acta Helv. 74 (1999) 11-17.
51. S. N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivative with triazole, Arzneim. Forsch. 50 (2000) 55-60.
52. th ed., Weverly Publishers, New Delhi 1995, pp. 855.
53. Y. Teitz, D. Ronen, A. Vansover, T. Stematsky and J. L. Riggs, Inhibition of Human Immunodeficiency Virus by N-methyl isatin-beta-4′,4′- diethyl thiosemicarbazone and N-allyl isatin beta 4′,4′ diallyl thiosemicarbazones, Antiviral Res. 24 (1994) 305-314.
54. S. E. Webber, J. Tikhe, S. T. Worland, S. A. Fuhrman, T. F. Hendrickson, D. A. Mathews, R. A. Love and A. K. Patick, Synthesis and evaluation of non-peptidic inhibitors of Human Rhino Virus 3C Protease, J. Med. Chem. 39 (1996) 5072-5076.
55. F. Britcher and L. Susan, 3-Substituted Heterocyclic Inhibitors as Inhibitors of HIV Reverse Transcriptase, U.K. Pat. 2,282,808, 19 Apr 1995; ref. Chem. Abstr. 123 (1995) 143634d.
56. V. P. Joseph, M. Hollaway, G. Katharine and P. James, Combination of (Hydroxy indanyl) Piperazines Pentanamide II and 1697661 as HIV Protease Inhibitor, Eur. Pat. 617, 968, 05 Oct 1994; ref. Chem. Abstr. 123 (1995) 198639q.
57. M. Artico, S. Marsa, L. Romano, G. Anna, A. Demontis and P. Lacella, Preparation of 1H-pyrrol-1-yl and 1H-indol-1-yl Aryl Sulfones for Treatment of HIV-I-Infections, Ital. Pat. 96,33,171,21 Apr 1995; ref. Chem. Abstr. 126 (1997) 187187e.
58. F. D. Popp and H. Pajouhesh, Potential anticonvulsants VI: Condensation of isatins with cyclohexanone and other cyclic ketones, J. Pharm. Sci. 72 (1983) 318-321.
59. N. H. Eshbha and H. M. Salama, 5-(2-Oxo-3-indolinylidene) thiazolidine-2,4-dione-1,3-di-Mannich base derivatives: Synthesis and evaluation for antileukemic activity, Pharmazie 40 (1985) 320-322.
60. Y. Teitz, E. Ladizensky, N. Barko and E. Burstein, Selective repression of V-alb encoded protein by N-methylisatin-beta-4′,4′-diethyl thiosemicarbazone and N-allylisatin-beta-′,4′- diallylthiosemicarbazone, Antimicrob. Agents Chem. Ther. 37 (1993) 2483-2486.
61. A. Broadbent, H. Thomas and S. Broadbent, The chemistry and pharmacology of indole-3-carbinol (indole-3-methanol) and 3-(methoxy methyl)-indole [Part II], Curr. Med. Chem. 5 (1998) 469-491.
62. J. Ramachandran, Antimycobacterial Isatin and Oxindole Derivatives for the Treatment of Mycobacterial Diseases, Swed. Pat. 9,944,608, 20 Apr 1998; ref Chem, Abstr. 131 (1999) 209113g.
63. R. S. Varma and R. K. Pandeya, Synthesis of 3-(p-(p-alkoxy carbonyl)phenyl)-carbonyl)-phenyl) imino)-2-indolinones as potentially biologically active agents, Indian J. Pharm. Sci. 46 (1982) 132-135.
64. J. Collino and S. Volpe, Mannich bases with dipiperidinic structure having pharmacological activity, Ital. Boll. Chim. Farm. 121 (1982) 408-420.
65. M. L. Gargari, R. C. Bansal, K. Singh and A. Mahmood, Inhibition of glucose transport in human erythrocytes by 2,3-dioxoindole (isatin), Experientia 50 (1994) 833-837.
66. D. Hota and S. B. Acharya, Studies on peripheral actions of isatin, Indian J. Exp. Biol. 32 (1994) 710-717.