171285-89-5

Upstream product

• 159615-86-8 2-methylthio-5-[(4R)-2,2,4-trimethyl-1,3-dioxolan-4-yl]thiazole 
• 161387-23-1 2-mercapto-5-[(4R)-2,2,4-trimethyl-1,3-dioxolan-4-yl]thiazole 
• 159615-85-7 (R)-5-(1,2-dihydroxyprop-2-yl)-2-(methylthio)thiazole 
• 161387-24-2 4'-{5-[(4R)-2,2,4-trimethyl-1,3-dioxolan-4-yl]thiazol-2-ylthio}acetophenone 
• 171482-68-1 1-{4-[5-((R)-2,2,4-Trimethyl-[1,3]dioxolan-4-yl)-thiazol-2-ylsulfanyl]-phenyl}-ethanone oxime 
• 590-17-0 cyanomethyl bromide 

Relevant academic research and scientific papers

Chiral Dioxolane Inhibitors of Leukotriene Biosynthesis: Structure-Activity Relationships and Syntheses Using Asymmetric Dihydroxylation

1,3-Dioxolanes have been described as chiral inhibitors of 5-lipoxygenase (5LO).In the present work, this series has been developed further to provide agents which showed comparable or superior potency in vivo to ZD2138, a methoxytetrahydropyran inhibitor of 5LO, which is currently undergoing clinical evaluation.An asymmetric synthesis was developed to these dioxolanes based on asymmetric dihydroxylation. (S)-N-Methyl-4'-thio>acetanilide ((S)-10d) inhibited leukotriene B4 (LTB4) synthesis in A23187-stimulated human whole blood in vitro with IC50 0.039μM, 25-fold more potent than (R)-10d.In vivo, (S)-10d inhibited LTB4 synthesis by 70percent in zymosan-inflamed air pouch exudate in rat 10 h after an oral dose of 1.5 mg/kg.Structure-activity relationship considerations suggested that the dioxolane and methoxytatrahydropyran series are related, a conclusion which can be supported by molecular modeling.