2781-29-5Relevant 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.
REDUCTIVE COUPLING OF α,β-ENONES I : REDUCTION OF METHYL-VINYL KETONE AND MESITYL OXIDE.
Pons, Jean-Marc,Zahra, Jean-Pierre,Santelli, Maurice
, p. 3965 - 3968 (2007/10/02)
Reductive coupling of methyl-vinyl ketone with TiCl4-Mg gives pinacol 1 (25percent).According to the reducing agents, mesityl oxide yields 2,4,5,7-tetramethyl-octa-2,4,6-triene 3 (with 4TiCl3-LiAlH4), triene 3 or 2,4,5,7-tetramethyl-octa-2,6-dien-4,5-diol 5 (with TiCl4-Mg), pinacol 5 (with VCl3-Mg), and 2-acetyl-1,3,3,4,4-pentamethyl-cyclopentene 7 (with CrCl3-Mg or FeCl3-Mg or ZrCl4-Mg) as major products.
