A new biologically active molecular scaffold: crystal structure of 7‐(3‐hydroxyphenyl)‐4‐methyl‐2H‐[1, 2, 4]triazolo[3, 2‐c][1, 2, 4]triazole and selective antiproliferative activity of three isomeric triazolo–triazoles. Issue 10 (25th September 2019)

• Record Type: Journal Article
• Authors: Fusco, Sandra; Capasso, Domenica; Centore, Roberto; Di Gaetano, Sonia; Parisi, Emmanuele
• Is Part Of: Acta crystallographica. Volume 75:Issue 10(2019)
• Page Start: 1398
• Page End: 1404
• Publication Date: 2019-09-25
• Subjects: heterocycle -- triazole -- cytotoxicity -- antiproliferative -- crystal structure; Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229619012403
• Languages: English
• ISSNs: 2053-2296

Abstract

Abstract : We have considered a set of three isomeric 7‐(hydroxyphenyl)‐4‐methyl‐2 H ‐[1, 2, 4]triazolo[3, 2‐ c ][1, 2, 4]triazole molecules differing in the position of the hydroxy group in the phenyl ring ( ortho, meta and para ). The three compounds were tested for antiproliferative activity against some cancer cell lines, showing different activities and, in one case, i.e. the meta isomer, a certain degree of selectivity between cancer cell lines and normal cell lines. Abstract : 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 (C10 H9 N5 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 21 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.