221656-71-9

Upstream product

• 221656-69-5 1,8-dihydroxy-2,6-dimethyl-1-phenyl-2(E),6(E)-octadiene 
• 37905-02-5 (2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate 
• 37905-03-6 8-hydroxygeranyl acetate 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 95763-58-9 3,7-dimethyl-8-<(tetrahydro-2H-pyran-2-yl)oxy>-2E,6E-octadien-1-ol 
• 108-86-1 bromobenzene 
• 203381-39-9 3,7-dimethyl-8-phenyl-2(E),6(E)-octadienol 

Downstream Products

• 221656-72-0 N,N,3,7-tetramethyl-8-phenyl-2(E),6(E)-octadienylamine 

Relevant academic research and scientific papers

Synthesis and antimicrobial evaluation of farnesyl diphosphate mimetics

The synthesis and first antimicrobial evaluation of farnesyl diphosphate mimetics are described. Several analogues (10, 12, 13, and 20) are inhibitors of Candida albicans, Shizosaccharomyces pombe, and Saccharomyces cerevisiae. The activities of analogues 10, 12, and 13, which contain a ω-phenyl moiety and a diphosphate isostere, are not attributable to inhibition of sterol biosynthesis via squalene synthase. Two geranyl phenylsulphones (14 and 15) are potent inhibitors of Escherichia coli. Analogue 15 exhibits potent activity towards Salmonella typhimurium and Pseudomonas aeruginosa (MIC - 2μg/mL) and represents the first type of semi-synthetic terpenoid allylic sulphone active against these bacteria.

Zwitterionic sulfobetaine inhibitors of squalene synthase

A substantial number of sulfobetaines (e.g., 10) have been synthesized and evaluated as inhibitors of squalene synthase (SS) on the basis of the idea that their zwitterionic structure would have properties conducive both to binding in the active site and to passage through cell membranes. When the simple sulfobetaine moiety is incorporated into compounds containing hydrophobic portions like those in farnesyl diphosphate (1) or presqualene diphosphate (2), inhibition of SS in a rat liver microsomal assay was indeed observed. For example, farnesylated sulfobetaine 10 has IC50 = 10 μM and aromatic derivative 35 has IC50 = 2 μM for SS inhibition. A wide variety of structural modifications, exemplified by compounds 43, 52, 76, 85, 91, 99, 111, and 115, was investigated. Unfortunately, no inhibitors in the submicromolar range were discovered, and exploration of a different type of zwitterion seems necessary if this appealing approach to inhibition of SS is going to provide a potential antihypercholesterolemic agent.