128434-29-7

Upstream product

• 54730-30-2 4-hydroxy-3-C-prenylbenzaldehyde 
• 3188-13-4 ethyl chloromethyl ether 
• 123-08-0 4-hydroxy-benzaldehyde 
• 115-18-4 2-methyl-3-buten-2-ol 

Downstream Products

• 1608121-21-6 (Z)-5-(4-hydroxy-3-(3-methylbut-2-en-1-yl)benzylidene)-4-(4-hydroxyphenyl)furan-2(5H)-one 
• 130236-68-9 amorilin 4',5,7-trisethoxymethyl ether 
• 130322-09-7 euchrenone a3 
• 130236-67-8 4,4',6'-trisethoxymethoxy-2'-hydroxy-3,3',5'-tri-C-prenylchalcone 

Relevant academic research and scientific papers

Efficient, collective synthesis and nitric oxide inhibitory activity of rubrolides E, F, R, S and their derivatives

An efficient first synthesis of biologically significant natural butenolides, rubrolides F (1f), R (1r), S (1s) & its 7″,8″-didehydro derivative (1sa), and 3″-bromo rubrolide (1fa) along with the synthesis of rubrolide E (1e) and its di-O-methyl derivative (1ea) is accomplished in a collective fashion from commercially available and inexpensive precursors in overall yields of 14–48.5%. Key features are Wittig-Horner reaction, SeO2-induced tandem allylic hydroxylation/intramolecular cyclization and Knoevenagel condensation. Next, in their inhibitory activity towards nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 macrophages as an indicator of anti-inflammatory activity, all compounds displayed good inhibitory activity in a concentration-dependent manner. None of the compound exhibited notable cytotoxicity at the highest concentration (10?μM) and IC50values are found in the range from 8.53 to 17.85?μM.

Synthetic method for rubrolide compounds E, F, R, S and their derivatives

Rubrolide F (compound 1f), R (compound 1r), and S (compound 1s), which are biological important natural butenolides, 7andPrime;,8andPrime;-didihydro derivatives (compound 1sa) thereof, 3andPrime; -bromorubrolide (compound 1fa), rubrolide E (compound 1e) and di-O-methyl derivatives thereof (compound 1ea) can be industrially obtained and are effectively synthesized with the overall yield of 14-48.5% from low-priced precursors. The rubrolide compounds can be synthesized through a Knoevenagel condensation reaction after a Wittig-Horner reaction and SeO_2-induced tandem allylic hydroxylation/intramolecular cyclization for preparing butenolide rings and a rubrolide cores structure.COPYRIGHT KIPO 2017