title: Stability, Kinetic, and Mechanistic Investigation of 1,8-Self-Immolative Cinnamyl Ether Spacers for Controlled Release of Phenols and Generation of Resonance and Inductively Stabilized Methides.
abstract: Three cinnamyl ether spacers (non-methyl, α-methyl, and γ-methyl) for caging of phenols have been synthesized and are physiologically stable. When triggered, the γ-methyl spacer releases phenols (pKa7.8 and 9.8) with a t1/2< 30 s and <2 min in aqueous and aqueous-organic solvent, respectively. The α-methyl spacer releases a phenol (pKa7.8) with a t1/2= 27 and 54 min. For the γ-methyl spacer, the results suggest the presence of a resonance and inductively stabilized aza-cinnamyl methide.
authors.affiliation: New Zealand's National School of Pharmacy, University of Otago , Dunedin 9054, New Zealand.
authors.forename: Siddharth S
authors.initials: SS
authors.lastname: Matikonda
authors.affiliation: New Zealand's National School of Pharmacy, University of Otago , Dunedin 9054, New Zealand.
authors.forename: Jessica M
authors.initials: JM
authors.lastname: Fairhall
authors.affiliation: New Zealand's National School of Pharmacy, University of Otago , Dunedin 9054, New Zealand.
authors.forename: Joel D A
authors.initials: JD
authors.lastname: Tyndall
authors.affiliation: New Zealand's National School of Pharmacy, University of Otago , Dunedin 9054, New Zealand.
authors.forename: Sarah
authors.initials: S
authors.lastname: Hook
authors.affiliation: New Zealand's National School of Pharmacy, University of Otago , Dunedin 9054, New Zealand.
authors.forename: Allan B
authors.identifier: 0000-0001-5440-8771
authors.initials: AB
authors.lastname: Gamble