Synthesis of Schiff and Mannich bases of isatin derivatives with 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones

Molecules

Volumn 13, Issue 9, 2008, Pages 2126-2135

  Bekircan, Olcay ^a   Bektas, Hakan ^b  

^a KARADENIZ TECHNICAL UNIVERSITY   (Turkey)

^b GIRESUN UNIVERSITY   (Turkey)

Author keywords

4 amino 1,2,4 triazole 5 one; Ethoxycarbonyl hydrazones; Ethyl imidate hydrochloride; Isatin; Mannich bases; Schiff bases

Indexed keywords

ISATIN; MANNICH BASE; SCHIFF BASE; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ISATIN; MAGNETIC RESONANCE SPECTROSCOPY; MANNICH BASES; MOLECULAR STRUCTURE; SCHIFF BASES; SPECTROPHOTOMETRY, INFRARED; TRIAZOLES;

EID: 53249095791     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13092126     Document Type: Article

References (35)

1. Karia, F.D.; Parsania, P.H. Synthesis, biological and thermal properties of schiff bases of bisphenol-C. Asian J. Chem. 1999, 11, 991-995.
2. Tarafder, M.T.; Kasbollah, A.; Saravan, N.; Crouse, K.A.; Ali, A.M.; Tin, O.K. S-methyldithiocarbazate and its schiff bases: Evaluation of bondings and biological properties. J. Biochem. Mol. Biol. Biophs. 2002, 6, 85-91.
3. Küçükgüzel, İ.; Küçükgü zel, Ş.G.; Rollas, S.; Ötük-Saniş, G.; Özdemir, O.; Bayrak, İ.; Altuǧ, T.; Stables, J.P. 3-(Arylalkylthio)-4-alkyl/ aryl-5-(4-aminophenyl)-4H-1,2,4-triazole derivatives and their anticonvulsant activity. Farmaco. 2004, 59, 893-901.
4. Vicini, P.; Geronikaki, A.; Incerti, M.; Busonera, B.; Poni, G.; Kabras, C.A.; Colla, P.L. Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases. Bioorg. Med. Chem. 2003, 11, 4785-4789.
5. Kahveci, B.; Bekircan, O.; Karaoglu, SA. Synthesis and antimicrobial activity of some 3-alkyl-4-(arylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5- ones. Indian J. Chem. 2005, 44B, 2614-2617.
6. Bekircan, O.; Kahveci, B.; Kucuk, M. Synthesis and anticancer evaluation of some new unsymmetrical 3,5-diaryl-4H-1,2,4-triazole derivatives. Tur. J. Chem. 2006, 30, 29-40.
7. Singh, W.M.; Dash, B.C. Synthesis of some new schiff bases containing thiazole and oxazole nuclei and their fungicidal activity. Pesticides 1988, 22, 33-37.
8. Holla, B.S.; Shivananda, M.K.; Shenoy, M.S.; Antony, G. Synthesis and characterization of some mannich bases carrying halophenylfuryl moieties as promising antibacterial agents. Farmaco. 1998, 53, 531-535.
9. Holla, B.S.; Veerendra, B.; Shivananda, M.K.; Poojary, B. Synthesis characterization and anticancer activity studies on some mannich bases derived from 1,2,4-triazoles. Eur. J. Med. Chem. 2003, 38, 759-767.
10. Gokce, E.; Bakir, G.; Sahin, M.F.; Kupeli, E., Yesilada, E. Synthesis of new mannich bases of arylpyridazinones as analgesic and anti-inflammatory agents. Arzneim. Forsch. 2005, 55, 318-325.
11. Dimmock, J.R.; Jonnalagadda, S.S.; Phillips, O.A.; Erciyas, E.; Shyam, K.; Semple, H.A. Anticonvulsant properties of some mannich bases of conjugated arylidene ketones. J. Pharm. Sci. 1992, 81, 436-440.
12. Lopes, F.; Capela, R.; Goncaves, J.O.; Horton, P.N.; Hursthouse, M.B.; Iley, J.; Casimiro, C.M.; Bom, J.; Moreire, R. Amidomethylation of amodiaquine: antimalarial N-mannich base derivatives. Tetrahedron Lett. 2004, 45, 7663-7666.
13. Sriram, D.; Bal, T.R.; Yogeesswari, P. Synthesis, antiviral and antibacterial activities of isatin mannich bases. Med. Chem. Res. 2005, 14, 11-28
14. Knabe, J.; Buch, H.P.; Schmitt, W. Derivatives of barbituric acid cytostatic and CNS activities of chiral barbiturate mannich-bases. Arch. Pharm. Chem. Life Sci. 1983, 316, 1051-1053.
15. Islam, M.R.; Abedin, M.J.; Hossain M.M.; Duddeck, H. Synthesis of 1-methyl bis-dioxopyrolino [2,3:2,3:2,3:6,5] benzene and its heterocycles via thiocarbohydrazone, thiosemicarbazone. J. Bangladesh Chem. Soc. 1998, 11, 71-78.
16. Sarangapani, M.; Reddy, V.M. Pharmacological evaluation of 1-(N,N-disubstituted aminomethyl)-3-imino-(2-phenyl-3,4-dihydro-4-oxo- quinazolin-3-yl) indolin-2-ones. Indian J. Pharm. Sci. 1994, 56, 174-177.
17. Pandeya, S.N.; Sriram, D.; Nath, G.; De Clercq, E. Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of isatin and their derivatives. Pharm. Acta Helv. 1999, 74, 11-17.
18. Popp, F.D.; Parson, R.; Donigan, B.E. Potential anticonvulsants the condensation of isatin with cyclic-ketones. J. Heterocycl. Chem. 1980, 17, 1329-1330.
19. Pandeya, S.N.; Sriram, D.; DeClercq, E.; Nath, G. 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.
20. 13C-NMR and anticonvulsant activity of new isatin-based spiroazetidinones. Indian J. Chem. 1997, 36B, 951-954.
21. Bhattacharya, S.K.; Chakrabarti S. Dose-related proconvulsant and anticonvulsant activity of isatin, a putative biological factor in rats. Indian J. Exp. Biol. 1998, 36, 118-121.
22. Legrand, C.; Ropaa, P.; Vulturescu, B.; Hogeac, A.M.; Surpateanu, G.G.; Cazier, F.; Woisel, P.; Surpateanu, G. Electrical properties of some 1,2,4-triazole derivatives. Progress in Organic Coatings 2005, 53, 106-111.
23. Ewiss, N.F.; Bahajaj, A.A.; Elsherbini, E.A. Synthesis of heterocycles, Part VI-Synthesis and antimicrobial activity of some 4-amino-5-aryl-1,2,4- triazole-3-thions and their derivatives. J. Heterocycl. Chem. 1986, 23, 1451-1458.
24. Eweiss, N.F.; Bahajaj, A.A. Synthesis and antimicrobial activity of some 7H-s-triazolo[3,4-b][1,3,4]thiadiazine and s-triazolotriazolo[3,4- b][1,3,4]thiadiazole Derivatives. J. Heterocycl. Chem. 1987, 24, 1173-1182.
25. Prasad, A.; Ramalingam, R.J.; Rao, A.B.; Diwan, P.V.; Sattur, P.B. Synthesis and biological evaluation of 3-aryloxyalkyl-6-aryl-7H-s-triazolo[3,4-b][1,3,4]thiadiazines. Eur. J. Med. Chem. 1989, 24, 199-201.
26. Turan-Zitouni, G.; Kaplancikli, Z.A.; Yildiz, M.T.; Chevallet, P.; Kaya, D. Synthesis and antimicrobial activity of 4-phenyl/cyclohexyl-5-(1- phenoxyethyl)-3-[N-(2-thiazolyl)acetamido]-thio-4H-1,2,4-triazole derivatives. Eur. J. Med. Chem. 2005, 40, 607-613.
27. Chen, J.; Sun, X.Y.; Chai, K.Y.; Lee, J.S.; Song, M.S.; Quan, Z.S. Synthesis and anticonvulsant evaluation of 4-(4-alkoxylphenyl)-3-ethyl-4 H-1,2,4-triazoles as open-chain analogues of 7-alkoxyl-4,5-dihydro[1,2,4] triazolo[4,3-a]quinolines. Bioorg. Med. Chem. 2007, 15, 6775-6781.
28. Bekircan, O.; Gumrukcuoglu, N. Synthesis of Some 3,5-diphenyl-4H-1,2,4- triazole derivatives as antitumor agents. Indian J. Chem. 2005, 44B, 2107-2113.
29. Turan-Zitouni, G.; Kaplancikli, Z.A.; Erol, K.; Kilic, F.S. Synthesis and analgesic activity of some triazoles and triazolothiadiazines. Farmaco 1999, 54, 218-223.
30. Akhtar, T.; Hameed, S.; Al-Masoudi, N. A.; Khan, K.M. Synthesis and anti-HIV activity of new chiral 1,2,4-triazoles and 1,3,4-thiadiazoles. Heteroatom. Chem. 2007, 18, 316-322.
31. Turan-Zitouni, G.; Kaplancikli, Z.A.; Özdemir, A.; Chevallet, P. Studies on 1,2,4-triazole derivatives as potential anti-iInflammatory agents. Arch. Pharm. Chem. Life Sci. 2007, 340, 586-590.
32. Pandeya, S.N.; Sriram, D.; Nath, G.; de Clercq, E. Synthesis, antibacterial, antifungal and anti HIV evaluation of schiff and mannich bases of isatin and its derivatives with triazole. Arzneimittel Forsch. 2000, 50, 55-59.
33. Kahveci, B. Synthesis of 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones and their isatin-3-imine derivatives. Molecules 2005, 10, 376-382.
34. Kelley, J.L.; Linn, J.A.; Bankston, D.D.; Burchall, C.J.; Soroko, F.E.; Cooper, B.R. 8-Amino-3-benzyl-1,2,4-triazolo[4,3-a]pyrazines.Synthesis and anticonvulsant activity. J. Med. Chem. 1995, 38, 3676-3679.
35. Huang, Z.; Liu, Z. Synthesis of 2-(Benzoylmethylene)imidazolidines and hexahydropyrimidines by condensation of ethyl benzoylacetimidates with 1,2-ethanediamine or 1,3-propandiamine, and some addition Reactions. Synthesis 1987, 4, 357-362.