63621-95-4Relevant 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.
Synthesis of the tetracyclic core of exiguaquinol
Schwarzwalder, Gregg M.,Steinhardt, Sarah E.,Pham, Hung V.,Houk,Vanderwal, Christopher D.
supporting information, p. 6014 - 6017 (2014/01/06)
A Diels-Alder reaction, a desymmetrizing aldol reaction, and a reductive Heck cyclization are employed in a short synthesis of a tetracycle relevant to exiguaquinol, a potential antibiotic. Ground-state energies of this advanced model system and the natural product rationalize the incorrect hemiaminal configuration experimentally obtained and point to the importance of the sulfonate in dictating the relative configuration of the natural product.
Preparation of p,p'-Disubstituted-α,ω-Diphenyl Polyenes
Spangler, Charles W.,McCoy, Ray K.,Dembek, Alexa A.,Sapochak, Linda S.,Gates, Bradley D.
, p. 151 - 154 (2007/10/02)
Condensation of appropriately substituted benzaldehydes or cinnamaldehydes with either bis-Wittig reagents or bis-phosphonate esters (Horner-Emmons-Wadsworth modifications) containing one or two double bond units are general and quite efficient preparatio
Derivatives of 2,3-anhydro-DL-threitol, 2,3-anhydroerythritol, 2,3:4,5-dianhydrogalactitol, and 2,3:4,5-dianhydroallitol.
Schneider,Horvath,Sohar
, p. 43 - 52 (2007/10/11)
alpha, omega-Disubstituted derivatives of 2,3-anhydro-DL-threitol (2), 2,3-anhydroerythritol (4), 2,3:4,5-dianhydrogalactitol (8), and 2,3:4,5-dianhydroallitol (12) have been synthesised by epoxidation of the appropriate alkeness and dienes. Benzyloxy car
