Synthesis and anticancer activity of some new s-triazine derivatives
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Med Chem Res DOI 10.1007/s00044-013-0584-6
ORIGINAL RESEARCH
Synthesis and anticancer activity of some new s-triazine derivatives G. Jagadeesh Kumar • H. V. S. Sriramkumar Bomma E. Srihari • Shweta Shrivastava • V. G. M. Naidu • Kolupula Srinivas • V. Jayathirtha Rao
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Received: 10 December 2012 / Accepted: 13 March 2013 Ó Springer Science+Business Media New York 2013
Abstract New s-triazine derivatives 13a–h were synthesized for the structure–activity relationship studies as potent anticancer agents. The prepared analogues were evaluated for their in vitro inhibitory activity against the growth of PA-1 (Ovarian cancer), A549 (Lung cancer), MCF-7 (Breast cancer), and HT-29 (Colon cancer). Tri-substituted s-triazine derivatives (13e–h) with morpholino group on s-triazine scaffold exhibited potent anticancer activities compared to di-substituted s-triazine derivatives. Compounds 13e–h also showed relatively selective PA-1 and HT-29 cancer cell inhibition over other cancer cell lines. Structure–activity relationships provided useful insights in these classes of compounds and paved the way to design novel analogues with more potency. Keywords S-triazine derivatives Anticancer activity Structure–activity relationships Hit identification
G. Jagadeesh Kumar H. V. S. Sriramkumar Bomma E. Srihari V. Jayathirtha Rao (&) Crop Protection Chemicals Division, CSIR-Indian Institute of Chemical Technology, Uppal Road Tarnaka, Hyderabad 500607, India e-mail: [email protected] G. Jagadeesh Kumar H. V. S. Sriramkumar Bomma S. Shrivastava V. G. M. Naidu (&) K. Srinivas (&) V. Jayathirtha Rao National Institute of Pharmaceutical Education and Research (NIPER), Balanagar, Hyderabad 500037, India e-mail: [email protected] K. Srinivas e-mail: [email protected]; [email protected]
Introduction s-Triazine is a six-membered heterocyclic ring, with three nitrogens situated at 1st, 3rd and 5th positions. Its analogues, melamine, cyanuric acid and cyanuric chloride are important starting compounds for various materials with wide range of applications in textile, plastic, pharmaceuticals and rubber industries. These compounds are also used as pesticides, dyestuffs, optical bleaches, explosives and surface active agents (Bartholomew, 1996; Comins and O’Connor, 1988; Quirke, 1984; Smolin and Rapport, 1959). s-Triazine compounds have been studied extensively and are the subject of many reviews (Blotny, 2006; Giacomelli et al., 2004; Sathiakumar et al., 2011; Therrien, 2010). This s-triazine scaffold attracted many researchers, as its symmetrical structure facilitates to synthesize diverse set of analogues (ease of synthesis) such as 2, 4, 6-mono, di- or tri-substituted, symmetrical and nonsymmetrical compounds bearing different substituents and in particular, cyanuric chloride is the most important one in this aspect (Blotny, 2006). The s-triazine scaffold also provides the basis for the design of biologically relevant molecules with widespread application as therapeutics. For example, these compounds pos
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