Biopolymers and cell. Volume 20. № 1-2. 132-142.

L. H. Pal'chykovska, M. O. Platonov, I. V. Alexeeva, A. D. Shved

Design of the potential transcription inhibitors based on the 6-azacytosine and 6-aza-iso-cytosine. Nonempirical quantum chemical analysis, synthesis and physico-chemical studies

Summary

High tautomeric and conformation variability of the 6-aza-iso-cytosine aminoderivatives has been first found by the ab initio quantum chemical method on the B3LYP/6-31G(d, p)//HF/6-31G(d, p) theory level. This fact allows suggesting «universal nature» of these aminoderivatives, i. e. their ability to form pairs with both purine and pyrimidine canonic nucleic bases. Proceeding from the theoretical conformation analysis based on the functionally substituted 3- and 5-aminoderivatives as-triazine through the target synthesis the design of the potential inhibitors of NA synthesis was performed. The electronoacceptory properties of the aryl fragment in the synthesized compounds were experimentally found to induce the significant displacement of the high electronic density centers within as-triazine molecule that promotes rather free migration of the NH-proton thus contributing directly to its tautomeric status.