Synthesis and theoretical characterization of some new 4-substituted-1,3-diphenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazoles with potential pharmacological activity

✍ Scribed by Agata Siwek; Monika Wujec; Maria Dobosz; Piotr Paneth

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 90 KB
• Volume: 19
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20499

✦ Synopsis

Abstract

Synthesis of some new triazoles fused to triazoles 5a–c or thiadiazoles 6a–c and the thiol‐thione tautomeric equilibrium study of the title compounds are reported. The “rule of five” and complementary criteria of pharmacokinetic properties were determined to predict whether these compounds are orally bioavailable. Semiempirical parameterizations have been critically benchmarked for the thiol‐thione tautomeric equilibrium against the DFT calculations. It was shown that unlike the AM1 and PM3 Hamiltonians, which erroneously predict higher stability of the thiol tautomer, the newly developed RM1 Hamiltonian, on the other hand, predicts energetics of this equilibrium in excellent agreement with the DFT results. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:713–718, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20499