Crystal structures and biological activity of 1,1,4-triphenyl-substituted 1,3-enyne compounds
Fecha
2019
Tipo
artículo original
Autores
Pineda Cedeño, Leslie William
Arias Echandi, María Laura
Cabezas Pizarro, Jorge A.
Título de la revista
ISSN de la revista
Título del volumen
Editor
Resumen
1,3-Enyne structural motifs are versatile building blocks in organic synthesis and
occur widely in various natural products with many of them being highly active
as cytotoxic macrolides and antitumour antibiotics. This article presents the
crystal structure of three 1,1,4-triphenyl-substituted 1,3-enynes, viz. 4-(2-
methylphenyl)-1,1-diphenylbut-1-en-3-yne, C23H18 (1), 4-(2-methoxyphenyl)-1,1-
diphenylbut-1-en-3-yne, C23H18O (2), and 4-(4-nitrophenyl)-1,1-diphenylbut-1-
en-3-yne, C22H15NO2 (3). The benzene ring at position 4 of the but-1-en-3-yne
group bears a weakly activating methyl group in compound 1, a moderately
activating methoxy group in 2 and a strongly deactivating nitro group in 3. The
crystal structures of 1 and 3 both have monoclinic symmetry, while that of 2 is
orthorhombic, and all of them have one molecule in the asymmetric unit. All
three compounds were investigated for their antibacterial and antifungal
activities. Interestingly, enyne 2 is the only compound tested that inhibited the
growth of Aspergillus niger.
Descripción
Palabras clave
Productos naturales, Actividad antifúngica, Estructura cristalina, 1,3-dilithiopropyne, 1,3-enyne, Antibacterial activity, Crystal structure, Antifungal activity, Natural products