Synthesis, in vitro cytotoxicity, and antibacterial studies of new asymmetric bis-1,2,4-triazoles
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Med Chem Res (2013) 22:2163–2173 DOI 10.1007/s00044-012-0209-5
ORIGINAL RESEARCH
Synthesis, in vitro cytotoxicity, and antibacterial studies of new asymmetric bis-1,2,4-triazoles Rohit Singh • Gurubasavaraj V. Pujar • Madhusudan N. Purohit • V. M. Chandrashekar
Received: 18 April 2012 / Accepted: 20 August 2012 / Published online: 4 September 2012 Ó Springer Science+Business Media, LLC 2012
Abstract A series of asymmetric bis-1,2,4-triazoles (4a–l) were synthesized from respective 1,2,4-triazole-3-thiocarbohydrazides (2a, b) via base catalyzed dehydrative cyclization of thiosemicarbazide intermediates (3a–l). The synthesized compounds were characterized by IR, 1 H-NMR, 13C-NMR, and Mass spectral studies. The asymmetric bis-1,2,4-triazole derivatives (4a–l) were evaluated for in vitro antioxidant activity by DPPH radical scavenging assay method. The compounds with significant antioxidant potential were evaluated for in vitro cytotoxicity by MTT assay method against HT29 (Human adenocarcinoma) and MDA-231 (Human breast cancer) cancer cell lines. All the synthesized compounds were evaluated for in vitro antibacterial activity against Bacillus subtilus (ATCC 6633), Staphylococcus aureus (ATCC-25923), Escherichia coli (ATCC-25922), and Pseudomonas aeruginosa (ATCC-27853). Keywords Asymmetric bis-1,2,4-triazoles DPPH radical scavenging MTT assay
Introduction Cancer is the second leading cause of death worldwide, following cardiovascular diseases. The World Health
R. Singh G. V. Pujar (&) M. N. Purohit Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Mysore 570015, India e-mail: [email protected] V. M. Chandrashekar Department of Pharmacology, HSK College of Pharmacy, Bagalokot, India
Organization has estimated 12 million deaths worldwide due to cancer in 2030. Although progress has been steadily made in cancer research to reduce mortality and improve survival, cancer still accounts for nearly 1 in every 4 deaths in the world (Jemal et al., 2009). Many symmetric and asymmetric bis-heterocyclic systems are drawing much attention in the recent past due to their wide spectrum of biological activity (Fucheng et al., 1999; Spicer et al., 2000; Holla et al., 2001; Al-Soud and Al-Masoudi, 2004; Zhang et al., 2006; Dabholkar and Ansari, 2008; Sztanke et al., 2008). Many dimeric compounds designed as bis-DNA intercalators were evaluated as anticancer agents (Purohit and Mayur, 2012). Some of these bis-intercalators were reported to possess highly selective cytotoxicity against human colon carcinoma (Yong et al., 2005; Denny, 2003). Many of the bis-1,2,4-triazoles have also been reported to possess wide spectrum of biological activity (Holla et al., 2000; Ghorab et al., 2000; Holla et al., 2002; Demirbas et al., 2004). On the other hand, the emergence of multidrug-resistant microorganisms is posing a serious challenge to the scientific community in developing newer and safer molecules for the treatment of infectious diseases. Resistant organisms like methicillin-resistant Staphylococc
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