50442-68-7Relevant academic research and scientific papers
Reductive and Bioreductive Activation is Controlled by Electronic Properties of Substituents in Conformationally-Constrained Anticancer Drug Delivery Systems
Weerapreeyakul, Natthida,Visser, Petra,Brummelhuis, Mathijn,Gharat, Laxmikant,Chikhale, Prashant J.
, p. 148 - 163 (2007/10/03)
Conformationally-constrained, anticancer drug delivery systems (TDDS) containing the methyl ester of melphalan (as a model drug) were synthesized using electron-withdrawing or electron-donating functional groups to modulate reductive and bioreductive activation. The electronic nature of substituents in TDDS was found to control reductive and bioreductive activation of TDDS, thus influencing drug delivery from TDDS.
Development of a Novel Redox-Sensitive Protecting Group for Amines Which Utilizes a Facilitated Lactonization Reaction
Wang, Binghe,Liu, Siming,Borchardt, Ronald T.
, p. 539 - 543 (2007/10/02)
Selective protection and deprotection of functional groups are essential components of modern organic and peptide synthesis.To cope with the demand for the synthesis of organic molecules and peptides with increasing complexity, there has been a need to develop novel protecting groups which are readily cleavable under fundamentally different conditions to ensure selective modifications of specified functional groups.This report is focused on the development of a redox-sensitive amine protecting group using a substituted quinone propionic acid (1a).The key feature of this protecting group is that upon reduction of the quinone 1 to the hydroquinone 2, it undergoes a spontaneous lactonization to release the functional group attached to the carboxyl group (HXR).High yields were achieved for both the protection and deprotection reactions, and the reduction conditions required for the deprotection are very mild (Na2S2O4 or electrochemically) and thus very compatible with most functional groups encountered in organic molecules and peptides.
