73770-41-9Relevant academic research and scientific papers
Revisiting Bromohexitols as a Novel Class of Microenvironment-Activated Prodrugs for Cancer Therapy
Johansson, Henrik,Hussain, Omar,Allison, Simon J.,Robinson, Tony V.,Phillips, Roger M.,Sejer Pedersen, Daniel
supporting information, p. 228 - 235 (2019/12/11)
Bromohexitols represent a potent class of DNA-alkylating carbohydrate chemotherapeutics that has been largely ignored over the last decades due to safety concerns. The limited structure?activity relationship data available reveals significant changes in cytotoxicity with even subtle changes in stereochemistry. However, no attempts have been made to improve the therapeutic window by rational drug design or by using a prodrug approach to exploit differences between tumour physiology and healthy tissue, such as acidic extracellular pH and hypoxia. Herein, we report the photochemical synthesis of highly substituted endoperoxides as key precursors for dibromohexitol derivatives and investigate their use as microenvironment-activated prodrugs for targeting cancer cells. One endoperoxide was identified to have a marked increased activity under hypoxic and low pH conditions, indicating that endoperoxides may serve as microenvironment-activated prodrugs.
Diversity-oriented synthesis of novel polycyclic scaffolds using polymer-bound reagents
Garcia-Cuadrado, Domingo,Barluenga, Sofia,Winssinger, Nicolas
supporting information; experimental part, p. 4619 - 4621 (2009/03/11)
A concise sequence utilizing a Petasis three component reaction followed by a tandem aza-Cope-Mannich cyclization afforded novel polycyclic heterocycles in good yield; alternative iminium cyclization based on a Pictet-Spengler reaction or aminal formation
Pyrrole Annulation onto Aldehydes and Ketones via Palladium-Catalyzed Reactions
Trost, Barry M.,Keinan, Ehud
, p. 2741 - 2746 (2007/10/02)
α-Dicarbonyl systems reacted with vinylmagnesium bromide and acetic anhydride to give α-acetoxy-α-vinylalkanones.These substrates react with benzylamine in the presence of tetrakis(triphenylphosphine)palladium to give N-benzylpyrroles with substituents in the two and/or three position.The functiodifferentiated synthesis of α-dicarbonyl compounds from ketones makes this a pyrrole annulation onto any α-methylene carbonyl system.
