Sterically congested quinone methides in photodehydration reactions of 4-hydroxybiphenyl derivatives and investigation of their antiproliferative activity
作者:Nikola Basarić、Nikola Cindro、Damir Bobinac、Kata Mlinarić-Majerski、Lidija Uzelac、Marijeta Kralj、Peter Wan
DOI:10.1039/c1pp05182b
日期:2011.12
In aqueous media, photochemical excitation (S1) of hydroxyadamantyl, diphenylhydroxymethyl, and hydroxypropyl derivatives of 4-phenylphenol 5–9 leads to solvent-assisted deprotonation of the phenol OH, and protonation of the benzyl alcohol coupled with dehydration, that delivers quinone methides (QMs) 14–18. The QMs react with CH3OH converting them in high quantum yields to the photosolvolysis products
groups of phenols/naphthols (42 compounds in total) were synthesized and screened against Gram-positive Staphylococcus aureus and Bacillus subtilis , Gram-negative Escherichia coli and Klebsiella pneumoniae , and the fungus Candida albicans . Whereas compounds were found inactive against Gram-negative bacteria, potent activities against Gram-positive bacteria were observed. The activities correlate