In:
Current Organic Chemistry, Bentham Science Publishers Ltd., Vol. 25, No. 12 ( 2021-07-14), p. 1441-1454
Abstract:
Synthesis of a series of 2-(dichloromethyl)pyrazolo[1,5-
a] [1,3,5]triazines was carried out and evaluated in vitro for their anticancer activity against a panel of 60 cell lines derived from nine cancer types. Methods: The joint quantum-chemical and experimental study of the influence of the extended
πconjugated phenyl substituents on the electron structure of the pyrazolo[1,5- a][1,3,5] triazines as Pharmacophores were performed. It is shown that the decrease in the
barriers to the rotation of phenyl substituents in compounds 1-7 possibly leads to an increase in the anti-cancer activity, which is in agreement with the change in the parameter biological
affinity Φ 0 . Analysis of the S0 → S1 electronic transitions (π→π*) of the pyrazolo[1,5-
a] [1,3,5]triazines shows that an increase in their intensity correlates with anti-cancer activity. Results: Thus, the introduction of phenyl substituents increases the likelihood of investigated
pyrazolo[1,5-a] [1,3,5]triazines interacting with protein molecules (Biomolecule) by the π-stacking mechanism. In both methyl and phenyl derivatives of pyrazolo[1,5-a][1,3,5] triazines, the second electronic transition includes the n-
MO (the level of the lone electron pair in two-coordinated nitrogen atoms). The highest intensity of the η→π* electronic transition is observed in pyrazolo[1,5-a][1,3,5] triazine with pyridine residue, which does not exhibit anticancer
activity, but exhibits antiviral activity [13] . Conclusion: It can be assumed that the possibility of the formation of [Pharmacophore-Biomolecule] complex by hydrogen bonding ([H-B]) mechanism with protein molecules increases.
Type of Medium:
Online Resource
ISSN:
1385-2728
DOI:
10.2174/1385272825666210607004536
Language:
English
Publisher:
Bentham Science Publishers Ltd.
Publication Date:
2021
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