Synthesis and biological evaluation of some Schiff bases of 4-amino-5-(4-methylsulfonyl)benzyl-2,4-dihydro-3 H -[1,2,4]-
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Med Chem Res DOI 10.1007/s00044-012-0294-5
ORIGINAL RESEARCH
Synthesis and biological evaluation of some Schiff bases of 4amino-5-(4-methylsulfonyl)benzyl-2,4-dihydro-3H-[1,2,4]-triazole3-thione V. Sumangala • Boja Poojary • N. Chidananda T. Arulmoli • Shalini Shenoy
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Received: 21 February 2012 / Accepted: 20 October 2012 Ó Springer Science+Business Media New York 2012
Abstract The basic nucleus 4-amino-5-[4-(methylsulfonyl)benzyl]-2,4-dihydro-3H-[1,2,4]-triazole-3-thione was prepared by cyclisation of potassium dithiocarbazinate with hydrazine hydrate using ethanol as solvent under reflux condition. The compound which has been synthesized successfully was subjected to addition reaction with different aldehydes to synthesize Schiff bases. The compounds were confirmed by spectroscopic methods (IR, NMR, and Mass). In order to ascertain the pharmaceutical application, the selective pharmacological screening of the derivatives was carried out according to the standard procedures. The compounds were screened for their cytotoxic activity and antimicrobial activity. Keywords Triazoles Schiff base Cytotoxicity Antimicrobial activity Introduction In the last two decades, the chemistry of [1,2,4]-triazole and their fused heterocyclic derivatives have received Electronic supplementary material The online version of this article (doi:10.1007/s00044-012-0294-5) contains supplementary material, which is available to authorized users. V. Sumangala B. Poojary (&) N. Chidananda Department of Chemistry, Mangalore University, Mangalagangothri 575199, Karnataka, India e-mail: [email protected] V. Sumangala T. Arulmoli SeQuent Scientific Limited, 120 A & B Industrial Area Baikampady, New Mangalore 575011, Karnataka, India S. Shenoy Department of Microbiology, KMC, Mangalore 575001, Karnataka, India
considerable attention owing to their synthetic and effective biological importance. [1,2,4]-Triazole moieties have been incorporated into variety of therapeutically interesting drug candidates including antiviral (Ribavirin), anti migraine (Rizatriptan), antifungal (Flucanazole), and antianxiety compounds (Alprazolam). Moreover, sulfur containing heterocyclic compounds represent an important group of compounds that are promising on practical application (Holla et al., 2003; Wu et al., 2007). The pharmacological importance of heterocycles derived from [1,2,4]-triazole paved the way toward active research in a triazole chemistry. As a result, variety of new compounds was being added to this field every year. A number of attempts were made to improve the activity of the compounds by varying the substituents on the triazole nucleus (Ragenovic et al., 2001; Mathew et al., 2007; Banachiewicz et al., 2004). Among these, the mercapto and amino group substituted [1,2,4]-triazole ring system have been reported for antituberculosis (Patole et al., 2006; Hearn and Cynamon, 2004), anticancer (Ren et al., 2002; Kuzmin et al., 2005), analgesic and anti-inflammatory (Ronad et al., 2008; Bhandari et al., 2008), anticonvulsant (Verma e
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