68486-78-2

Upstream product

• 68486-77-1 3-(4-(benzyloxy)phenyl)propanal 
• 68486-76-0 4-(2-benzyloxy-3,4-dimethoxyphenyl)-1-bromobutane 
• 634-36-6 1,2,3-trimethoxybenzene 
• 100-39-0 benzyl bromide 
• 68486-80-6 1-(4-hydroxyphenyl)-7-(2-hydroxy-3,4-dimethoxyphenyl)heptan-3-ol 
• 450357-58-1 2-hydroxy-3,4-dimethoxyallylbenzene 
• 850251-73-9 1-(4-(benzyloxy)phenyl)hex-5-en-3-ol 
• 74882-35-2 Toluene-4-sulfonic acid 4-(2-benzyloxy-3,4-dimethoxy-phenyl)-butyl ester 
• 74882-08-9 methyl 4-(2-benzyloxy-3,4-dimethoxyphenyl)butanoate 
• 74893-18-8 4-(2-benzyloxy-3,4-dimethoxyphenyl)butan-1-ol 
• 74882-06-7 methyl 4-(2-hydroxy-3,4-dimethoxyphenyl)butanoate 
• 74882-02-3 methyl 3-(2-hydroxy-3,4-dimethoxybenzoyl)propionate 
• 74882-05-6 4-(2-hydroxy-3,4-dimethoxyphenyl)butanoic acid 
• 68486-75-9 3-(2-hydroxy-3,4-dimethoxybenzoyl)propionic acid 

Downstream Products

• 74994-58-4 1-(4-benzyloxyphenyl)-7-(2-benzyloxy-5-bromo-3,4-dimethoxyphenyl)heptan-3-ol 
• 74994-43-7 (+/-)-1-(4-benzyloxyphenyl)-7-(2-benzyloxy-3,4-dimethoxy-5-iodophenyl)heptan-3-ol 
• 74994-44-8 (+/-)-1-(4-benzyloxy-3-iodophenyl)-7-(2-benzyloxy-3,4-dimethoxy-5-iodophenyl)heptan-3-ol 
• 68486-80-6 1-(4-hydroxyphenyl)-7-(2-hydroxy-3,4-dimethoxyphenyl)heptan-3-ol 
• 74994-68-6 (+/-)-dibenzylmyricanol 
• 68524-63-0 Acetic acid 5-(2-benzyloxy-5-bromo-3,4-dimethoxy-phenyl)-1-[2-(4-benzyloxy-phenyl)-ethyl]-pentyl ester 
• 68486-88-4 (+/-)-dibenzylmyricanol acetate 
• 68486-87-3 1-(4-benzyloxy-3-iodophenyl)-7-(2-benzyloxy-3,4-dimethoxy-5-iodophenyl)heptan-3-one 
• 68486-83-9 7-(2-Benzyloxy-5-bromo-3,4-dimethoxy-phenyl)-1-(4-benzyloxy-phenyl)-heptan-3-one 
• 68486-84-0 dibenzylmyricanone 
• 74882-34-1 1-(4-benzyloxyphenyl)-7-(2-hydroxy-3,4-dimethoxyphenyl)heptan-3-one 
• 32492-74-3 myricanone 
• 68510-47-4 (+/-)-myricanol 
• 68486-89-5 Acetic acid 5-(2-benzyloxy-3,4-dimethoxy-phenyl)-1-[2-(4-benzyloxy-phenyl)-ethyl]-pentyl ester 

Relevant academic research and scientific papers

New synthesized polyoxygenated diarylheptanoids suppress lipopolysaccharide-induced neuroinflammation

In neurodegenerative diseases, such as Alzheimer's disease, Huntington's disease, Parkinson's disease and multiple sclerosis, neuroinflammation induced by the microglial activation plays a crucial role. In effort to develop effective anti-neuroinflammatory compounds, different new linear polyoxygenated diarylheptanoids were synthesized. In LPS-triggered BV-2 microglial cells their ability to reduce the concentration of IL-6 and TNF-α pro-inflammatory cytokines was evaluated. Moreover, their effect on NF-κB and ATP citrate lyase (ACLY), a recently emerged target of metabolic reprogramming in inflammation, was assessed. Finally, we turned our attention to inflammatory mediators derived from the cleavage of citrate catalyzed by ACLY: prostaglandin E2, nitric oxide and reactive oxygen species. All compounds showed null or minimal cytotoxicity; most of them had a great anti-neuroinflammatory activity. Diarylheptanoids 6b and 6c, bearing a halide atom and benzyl ether protective groups, exhibited the best effect since they blocked the secretion of all inflammatory mediators analyzed and reduced NF-κB and ACLY protein levels.

Methods for the Construction of Linear 1,7-Diarylheptanoids; Synthesis of Di-O-methylcentrolobol and Precursors (Synthetic and Biosynthetic) to the meta,meta-Bridged Biphenyls Myricanol and Myricanone

1,7-diarylheptanoids are a varied natural product class in which 'linear' types appear to be biosynthetic precursors to macro(carbo)cyclic (3), macro(oxa)cyclic (4), and condensed polycyclic (5) examples.Various methods (suitable for radiolabelling) are described for constructing 'linear' diarylheptanoids, including Grignard couplings (employing activated magnesium) with arylpropanals and oxazonium salts (11a), (11h), (15a), and (15b)> and dithian alkylation (15c)>.Alkyl-lithium treatment of the benzyloxydithian (19b) gave 1,2,3-triphenylcyclopropane.Syntheses via trialkylcyanoborates were frustrated by disproportionation of the intermediate trialkylboranes.The diarylheptanoids synthesised (11a-h) and (15a-e) include synthetic and biosynthetic precursors to meta,meta-bridged biphenyls and related macrocyclic ethers.