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A new biologically active molecular scaffold: crystal structure of 7‐(3‐hydroxyphenyl)‐4‐methyl‐2 H ‐[1,2,4]triazolo[3,2‐ c ][1,2,4]triazole and selective antiproliferative activity of three isomeric triazolo–triazoles
Author(s) -
Fusco Sandra,
Capasso Domenica,
Centore Roberto,
Di Gaetano Sonia,
Parisi Emmanuele
Publication year - 2019
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229619012403
Subject(s) - moiety , chemistry , crystal structure , molecule , hydrogen bond , tautomer , stereochemistry , cancer cell lines , crystal (programming language) , triazole , crystallography , cancer cell , organic chemistry , medicine , cancer , computer science , programming language
A study of three isomeric compounds containing a phenolic moiety attached to the nitrogen‐rich triazolo–triazole bicycle is presented. In the three isomers, the phenolic OH group is in the ortho , meta and para positions. The crystal structure analysis of the meta isomer (C 10 H 9 N 5 O) shows that the 2 H ‐tautomer is present in the crystal and that the molecule adopts a substantially planar geometry. However, the conformation found in the crystal is different compared to the monoprotonated cation of the same compound previously investigated in several salts. The packing of the meta isomer is driven by the formation of strong hydrogen bonds and shows the formation of infinite planar ribbons, parallel to a , formed around 2 1 crystallographic axes. The three isomers were tested against some cancer cell lines and also against normal cell lines. The ortho isomer shows a weak antiproliferative activity, the meta isomer shows significant antiproliferative activity against some cancer lines and no activity against healthy cell lines, and the para isomer is active against all the tested cell lines.