Synthesis and physical-chemical properties of 3-benzyl-8-(5-mercapto-4-phenyl-[1,2,4]-triazole-3-ylmethylthiomethyl)xanthine and its s-substituted derivatives
DOI:
https://doi.org/10.14739/2409-2932.2015.2.45108Keywords:
Xanthines, Organic Synthesis, Infrared-Spectroscopy, NMR-spectroscopyAbstract
Aim. Currently, researches, devoted to obtain new active compounds, are carried out among various classes of organic compounds, and combination of several active heterocyclic fragments in one molecule is considered the key way in such researches.
Methods and results. For this purpose, we have developed a preparative method of synthesis of 3-benzyl-8-(5-mercapto-4-phenyl-[1,2,4]-triazole-3-ylmethylthiomethyl)xanthine and its S-substituted derivatives. On example of propyl ester of [5-(3-benzylxanthinyl-8-methylthiomethyl)-4-phenyl-[1,2,4]triazole-3-yl]thioacetic acid the possibility of further functionalization of triazolylmethylthiomethylxanthines has been shown.
Conclusion. The structures and identity of all synthesized compounds have been proved by elemental analysis, IR-, 1H NMR-spectroscopy, mass-spectrometry and by thin layer chromatography.
References
Bremner J. B., Ambrus J. I., & Samosorn S. (2007) Dual action-based approaches to antibacterial agents. Cur. Med. Chem., 2007, 14, 1459–1477. doi: 10.2174/092986707780831168.
Hubschwerlen, C., Specklin, J-L., Sigwalt, C., Sigwalt, C., Schroeder, S., & Locher, H. H. (2003) Design, synthesis and biological evaluation of oxazilidinone-quinolone hybrids. Bioorg. Med. Chem., 11(10), 2313–2319. doi: 10.1016/S0968-0896(03)00083-X.
Kalla, R. V., Elzein, Е., Perry, Т., Li, Х., Palle, V., Varkhedkar, V., et al. (2006) Novel 1,3-disubstituted 8-(1-benzyl-1H-pyrazol-4-yl)xanthines: high affinity and selective A2B adenosine receptor antagonists. J. Med. Chem, 49, 3682–3692.
Lin, R.-Y., Wu, B.-N., Lo, Y.-C., An, L.-M., Dai, Z.-K., Lin, Y.-T., et al. (2006) A Xanthine-Based Epithelium-Dependent Airway Relaxant KMUP-3 (7-[2-[4-(4-Nitrobenzene)piperazinyl]ethyl]-1,3-dimethylxanthine) Increases Respiratory Performance and Protects against Tumor Necrosis Factor-α-Induced Tracheal Contraction, Involving Nitric Oxide Release and Expression of cGMP and Protein Kinase G. J. Pharmacol. Exp. Ther, 316, 709–717. doi:10.1124/jpet.105.092171.
Allwood, M. B., Cannan, B., van Aalten, D. M. F., & Eggleston, I. M. (2007) Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy. Tetrahedron, 63, 12294–12302. doi:10.1016/j.tet.2007.09.067.
Baraldi, P. G., Tabrizi, M. A., Preti, D., Bovero, A., Fruttarolo, F., Romagnoli, R., rt al. (2004) [3H]-MRE 2029-F20, a selective antagonist radioligand for the human A2B adenosine receptors. Bioorg. Med. Chem. Let., 14, 3607–3610. doi:10.1016/j.bmcl.2004.03.084.
Varani, K., Gessi, S., Merighi, S., Vincenzi, F., Cattabriga, E., Benini, A., et al. (2005) Pharmacological characterization of novel adenosine ligands in recombinant and native human A2B receptors. Biochem. Pharmacol, 70, 1601–1612. doi:10.1016/j.bcp.2005.08.018.
Kaplaushenko, А. G., Panasenko, O. I., & Кnysh, E. G. (2007) Syntez, budova i protymikrobna aktyvnist 4-R-5-R1-3-heteryltio-1,2,4-tryazoliv [Synthesis, structure and antibacterial activity of 4-R-5-R1-3-heterylthio-1,2,4-triazols]. Farmatsevtychnyi zhurnal, 3, 88–91. [in Ukrainian].
Shalini K., Kumar, N., Drabu, S. & Sharma, P. K. (2011) Advances in synthetic aproach to and antifungal activity of triazoles. Beilstein J. Org. Chem., 7, 668–677. doi: 10.3762/bjoc.7.79.
Prasada, D. J., Ashokb, M., Karegoudarc, P., Poojarya, B., Hollad, B. S., & Kumarie N. S. (2009) Synthesis and antimicrobial activities of some new triazolothiadiazoles bearing 4-methylthiobenzyl moiety. European J. of Med. Chem, 2(44), 551–557. doi:10.1016/j.ejmech.2008.03.025.
Diachkov, M. V., Shkoda, O. S., Aleksandrova, К. V., & Levich, S. V. (2012) Syntez i fizyko-khimichni vlastyvosti hidrazydiv ta ilidenhidrazydiv 3-aryl-(aralkil)ksantynil-8)metyltioatsetatnykh kyslot [Synthesis and physicochemical properties of hydrazides and ylidenhydrazides of 3-aryl(aralkyl)-xanthinyl-8)methylthioacetic acids]. Zaporozhskij medicinskij zhurna, 3(72), 53–57. [in Ukrainian].
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