Synthesis and biological evaluation of some Schiff bases of 4-amino-5-(4-methylsulfonyl)benzyl-2,4-dihydro-3H-[1,2,4]-triazole-3-thione

Medicinal Chemistry Research

Volumn 22, Issue 6, 2013, Pages 2921-2928

  Sumangala, V ^a,b   Poojary, Boja ^a   Chidananda, N ^a   Arulmoli, T ^b   Shenoy, Shalini ^c  

^a MANGALORE UNIVERSITY   (India)

^b SeQuent Scientific Limited   (India)

^c KASTURBA MEDICAL COLLEGE   (India)

Author keywords

Antimicrobial activity; Cytotoxicity; Schiff base; Triazoles

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 4 {[(2 CHLORO 6 FLUOROPHENYL)METHYLENE]AMINO} 5 [4 (METHYLSULFONYL)BENZYL] 2,4 DIHYDRO 3H [1,2,4] TRIAZOLE 3 THIONE; 4 {[(2 CHLOROPHENYL)METHYLENE]AMINO} 5 [4 (METHYLSULFONYL)BENZYL] 2,4 DIHYDRO 3H [1,2,4] TRIAZOLE 3 THIONE; 4 {[(2 FLUOROPHENYL)METHYLENE]AMINO} 5 [4 (METHYLSULFONYL)BENZYL] 2,4 DIHYDRO 3H [1,2,4] TRIAZOLE 3 THIONE; 4 {[(2 FLUOROPHENYL)METHYLENE]AMINO} 5 [4 (METHYLSULFONYL)BENZYL] 2,4 DIHYDRO 3H [1.2.4] TRIAZOLE 3 THIONE; 4 {[(4 CHLOROPHENYL)METHYLENE]AMINO} 5 [4 (METHYLSULFONYL)BENZYL] 2,4 DIHYDRO 3H [1.2.4] TRIAZOLE 3 THIONE; 4 {[(4 FLUOROPHENYL)METHYLENE]AMINO} 5 [4 (METHYLSULFONYL)BENZYL] 2,4 DIHYDRO 3H [1,2,4] TRIAZOLE 3 THIONE; 4 {[(6 METHOXY 2 NAPHTHYL)METHYLENE]AMINO} 5 [4 (METHYLSULFONYL)BENZYL] 2,4 DIHYDRO 3H [1,2,4] TRIAZOLE 3 THIONE; 5 [4 (METHYLSULFONYL)BENZYL] 4 ({[4 (METHYLTHIO)PHENYL]METHYLENE}AMINO) 2,4 DIHYDRO 3H [1,2,4] TRIAZOLE 3 THIONE; 5 [4 (METHYLSULFONYL)BENZYL] 4 ({[THIOPHEN 2 YL]METHYLENE}AMINO) 2,4 DIHYDRO 3H [1,2,4] TRIAZOLE 3 THIONE; 5 [4 (METHYLSULFONYL)BENZYL] 4 {[(PYRIDIN 3 YL)METHYLENE]AMINO] 2,4 DIHYDRO 3H [1.2.4] TRIAZOLE 3 THIONE; ALCOHOL; ALDEHYDE; HYDRAZINE; POTASSIUM; POTASSIUM DITHIOCARBAZINATE; SCHIFF BASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYCLIZATION; CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 84879696485     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0294-5     Document Type: Article

References (18)

1. Banachiewicz BM, Banachiewicz J, Chodkowska A, Wojtowicz EJ, Mazur L (2004) Synthesis and biological activity of new derivatives of 3-(3,4-diaryl-[1,2,4]-triazole-5-yl)propenoic acid. Eur J Med Chem 39:873-887. doi: 10.1016/j.ejmech.2004.07.002
2. Bhandari SV, Bothara KG, Raut MK, Patil AA, Sarkate AP, Mokale VJ (2008) Design, synthesis and evaluation of anti-inflammatory, analgesic and ulcerogenicity studies of novel s-substituted phenacyl-[1,3,4]-oxadiazole-2- thiol and Schiff bases of diclofenac acid as nonulcerogenic derivatives. Bioorg Med Chem 16:1822-1831
3. Hearn MJ, Cynamon MH (2004) Design and synthesis of antituberculars: preparation and evaluation against Mycobacterium tuberculosis of an isoniazid Schiff base. J Antimicrob Chemother 53:185-191. doi: 10.1093/jac/dkh041
4. Holla BS, Veerendra B, Shivananda MK, Poojary B (2003) Synthesis characterization and anticancer activity studies on some Mannich bases derived from [1,2,4]-triazoles. Eur J Med Chem 38:759-767. doi: 10.1016/S0223-5234(03) 00128-4
5. Jarrahpour A, Khalili D, De Clercq E, Salmi C, Brunel JM (2007) Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of isatin and their derivatives. Molecules 12(8):1720-1730. doi: 10.3390/12081720
6. Kaplan JP, Raizon BM, Desarmenien M, Feltz P, Headley PM, Worms P, Lloyd KG, Bartholini G (1980) New anticonvulsants: Schiff bases of gamma-aminobutyric acid and gamma-aminobutyramide. J Med Chem 23(6):702-704. doi: 10.1021/jm00180a029
7. Kuzmin VE, Artemenko AG, Lozytska RN, Fedtchouk AS, Lozitsky VP, Muratov EN, Mescheriakov AK (2005) Investigation of anticancer activity of macrocyclic Schiff bases by means of 4D-QSAR based on simplex representation of molecular structure. SAR QSAR Environ Res 16(3):219-230
8. Mackie, McCartney (1989) In: Collee JG, Duguid JP, Fraser AG, Marmion BP (eds) Practical medicinal microbiology, 13th edn. Churchill Livingstone, London, p 87
9. Mathew V, Keshavayya J, Vaidya VP, Giles D (2007) Studies on synthesis and pharmacological activities of 3,6-disubstituted-[1,2,4]-triazolo-[3,4-b]-[1, 3,4]thiadiazoles and their dihydro analogues. Eur J Med Chem 42:823-840. doi: 10.1016/j.ejmech.2006.12.010
10. Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Meth 65:55-63
11. Patole J, Shingnapurkar D, Padhye S, Ratledge C (2006) Schiff base conjugates of p-aminosalicylic acid as antimycobacterial agents. Bioorg Med Chem Lett 16:1514-1517. doi: 10.1016/j.bmcl.2005.12.035
12. Ragenovic KC, Dimova V, Kakurinov V, Molnar DG, Buzarovaska A (2001) Synthesis, antibacterial and antifungal activity of 4-substituted-5-aryl-[1,2,4] -triazoles. Molecules 6:815-824. doi: 10.3390/61000815
13. Ren S, Wang R, Komatsu K, Bonaz-Krause P, Zyrianov Y, McKenna CE, Csipke C, Tokes ZA, Lien EJ (2002) Synthesis, biological evaluation and quantitative structure activity relationship analysis of new Schiff bases of hydroxysemicarbazide as potential antitumor agents. J Med Chem 45:410-419
14. Ronad P, Dharbamalla S, Hunshal R, Maddi V (2008) Synthesis of novel substituted 7-(benzylideneamino)-4-methyl-2H-chromen-2-one derivatives as anti-inflammatory and analgesic agents. Arch Pharm 341(11):696-700
15. Shi L, Ge HM, Tan SH, Li HQ, Song YC, Zhu HL, Tan RX (2007) Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde. Eur J Med Chem 42(4):558-564. doi: 10.1016/j.ejmech.2006.11.010
16. Sridhar SK, Pandeya SN, Stables JP, Ramesh A (2002) Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives. Eur J Pharm Sci 16(3):129-132. doi: 10.1016/S0928-0987(02)00077-5
17. Verma M, Pandeya SN, Singh KN, Stables JP (2004) Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharm 54(1):49-56
18. Wu J, Liu X, Cheng X, Cao Y, Wang D, Li Z (2007) Synthesis of novel derivatives of 4-amino-3-(2-furyl)-5-mercapto-[1,2,4]-triazole as potential HIV-1 NNRTIs. Molecules 12:2003-2016. doi: 10.3390/12082003