6468-84-4Relevant academic research and scientific papers
Synthesis of isobavachalcone and some organometallic derivatives
Grealis, John P.,Mueller-Bunz, Helge,Ortin, Yannick,Casey, Michael,McGlinchey, Michael J.
, p. 332 - 347 (2013/03/13)
Isobavachalcone [2′,4,4′-trihydroxy-3′-(3″-methyl- 2″-butenyl)chalcone, 1] is a prenylated chalcone that has broad biological activity, in particular against neuroblastomas, the most common cancer in infancy. It is currently commercially available at a cost of 190/mg by extraction from Psoralea corylifolia and a number of other African and Asian plants. Several synthetic routes have been explored, and the most efficient procedure involves the palladium-catalysed Stille coupling of 3-iodo-2,4-bis(methoxymethoxy)acetophenone (25) with prenyltributyltin, Claisen-Schmidt condensation with 4-(methoxymethoxy)benzaldehyde to form the triply MOM-protected prenylchalcone 27 and finally deprotection with 2 M HCl in methanol to form isobavachalcone in an overall yield of 15 % over five steps. The X-ray crystal structures of 2,4-dihydroxy-3-iodoacetophenone (21) and of several prenylated chalcones are reported, including the elucidation of their hydrogen-bonding networks in the solid state. The synthetic route has been extended to include organometallic derivatives in which the 4-(methoxymethoxy) benzaldehyde used in the Claisen-Schmidt condensation has been replaced by formylferrocene, formylruthenocene or (η5-formylcyclopentadienyl) (η4-tetraphenylcyclobutadiene)cobalt to form the corresponding analogues of isobavachalcone containing organometallic sandwich moieties.
Gold(I)-catalyzed intermolecular hydroarylation of allenes with nucleophilic arenes: scope and limitations
Tarselli, Michael A.,Liu, Ann,Gagné, Michel R.
experimental part, p. 1785 - 1789 (2009/06/28)
The addition of nucleophilic methoxyarenes to allenes proceeds at room temperature in dichloromethane with a catalytic amount of phosphite-gold(I) precatalyst and silver additive. The addition is regioselective for the allene terminus, and generates E-all
Synthesis and biological activity of the structural analogues of (-)-cabenegrin A-I
Gulacsi, Katalin,Litkei, Gyoergy,Antus, Sandor,Szantay, Csaba,Darko, Laszlo L.,Szelenyi, Judith,Hasko, Gyoergy,Vizi, Szilveszter E.
, p. 53 - 61 (2007/10/03)
A series of phenylbutene and butanol derivatives (6a-j, 12, 13, 15, 17, 24b,c, 26, 27a,b) were prepared from the readily available resorcinol derivatives 2a-f and 7-hydroxy-chroman (18). The products were tested for inhibitory activity on the LPS-induced
