Crystal structures and biological activity of 1,1,4-triphenyl-substituted 1,3-enyne compounds

Abstract

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.

Late transition metal complexes of ferrocene‐containing nitrogen ligands: Coordination chemistry, electron transfer properties, and tumor cell viability

“…Structures of 10b Ni and 10b Cu contained additional solvent-accessible areas in the structure and electron density from these voids was accounted for by SQUEEZE procedure of PLATON program. 54 Positions of hydrogen atoms bonded to carbon atoms were treated in the riding rigid-body model, that is, their positions were calculated according to the positions of the carbon atoms. C-H distances for aromatic and ferrocene H atoms were constrained to 0.93 Å and for methylene H atoms to 0.97 Å, respecting the elongation for measurement at a lower temperature (ligand 7, Table S2).…”