83814-58-8

Upstream product

• 83814-45-3 3-hydroxy-5,5-dimethyl-2-(2-methyl-1-piperidino)propylcyclohex-2-en-1-one 
• 3471-13-4 dimedone 
• 126-81-8 dimedone 

Downstream Products

• 83814-45-3 3-hydroxy-5,5-dimethyl-2-(2-methyl-1-piperidino)propylcyclohex-2-en-1-one 
• 1224866-14-1 2-(1-(3-acetyl-2,4,6-trihydroxy-5-(1-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-2-methylpropyl)phenyl)-2-methylpropyl)-3-hydroxy-5,5-dimethylcyclohex-2-enone 
• 1213776-86-3 3-hydroxy-5,5-dimethyl-2-(2-methyl-1-(2,4,6-trihydroxy-3-(1-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-2-methylpropyl)-5-isobutyrylphenyl)propyl)cyclohex-2-enone 
• 83814-62-4 2,4-diisopropyl-7,7-dimethyl-7,8-dihydro-4H-1,3-benzodioxin-5(6H)-one 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel myrtucommulones and structural analogues that target mPGES-1 and 5-lipoxygenase

The natural acylphloroglucinol myrtucommulone A (1) inhibits microsomal prostaglandin E2 synthase (mPGES)-1 and 5-lipoxygenase (5-LO), and induces apoptosis of cancer cells. Starting from 1 as lead, 28 analogues were synthesized following a straightforward modular strategy with high yielding convergent steps. Major structural variations concerned (I) replacement of the syncarpic acid moieties by dimedone or indandione, (II) cyclization of the syncarpic acid with the acylphloroglucinol core, and (III) substitution of the methine bridges and the acyl residue with isopropyl, isobutyl, n-pentyl or phenyl groups, each. The potency for mPGES-1 inhibition was improved by 12.5-fold for 43 (2-(1-(3-hexanoyl-2,4,6-trihydroxy-5-(1-(3-hydroxy-1-oxo-1H-inden-2-yl)-2-methylpropyl)phenyl)-2-methylpropyl)-3-hydroxy-1H-inden-1-one) with IC50 Combining double low line 0.08 μM, and 5-LO inhibition was improved 33-fold by 47 (2-((3-hexanoyl-2,4,6-trihydroxy-5-((3-hydroxy-1-oxo-1H-inden-2-yl) (phenyl)methyl)phenyl) (phenyl)methyl)-3-hydroxy-1H-inden-1-one) with IC50 Combining double low line 0.46 μM. SAR studies revealed divergent structural determinants for induction of cell death and mPGES-1/5-LO inhibition, revealing 43 and 47 as non-cytotoxic mPGES-1 and 5-LO inhibitors that warrant further preclinical assessment as anti-inflammatory drugs.

Plant Growth Regulators in Eucalyptus grandis. V Synthesis of the G-Regulators

Problems associated with earlier synthetic approaches to the G-regulators have been overcome by the use of the Mannich reaction in aprotic media.Under these conditions the Mannich base formed from the reaction of 1,3-diketones and aldehydes is stabilized by internal hydrogen bonding and can be isolated in high yield.In aqueous acid rapid elimination occurs to give the 2-methylene 1,3-diketones, which first enolize then add oxygen to generate the G-regulator structure.The steric limitations of the reactions are examined.