52922-73-3Relevant academic research and scientific papers
Novel, potent THC/anandamide (hybrid) analogs
Bourne, Caryl,Roy, Sucharita,Wiley, Jenny L.,Martin, Billy R.,Thomas, Brian F.,Mahadevan, Anu,Razdan, Raj K.
, p. 7850 - 7864 (2008/04/12)
The structure-activity relationship (SAR) of the end pentyl chain in anandamide (AEA) has been established to be very similar to that of Δ9-tetrahydrocannabinol (Δ9-THC). In order to broaden our understanding of the structural similarities between AEA and THC, hybrid structures 1-3 were designed. In these hybrids the aromatic ring of THC-DMH was linked to the AEA moiety through an ether linkage with the oxygen of the phenol of THC. Hybrid 1 (O-2220) was found to have very high binding affinity to CB1 receptors (Ki = 8.5 nM), and it is interesting to note that the orientation of the side chain with respect to the oxygen in the phenol is the same as in THCs. To further explore the SAR in this series the terminal carbon of the side chain was modified by adding different substituents. Several such analogs were synthesized and tested for their CB1 and CB2 binding affinities and in vivo activity (tetrad tests). The details of the synthesis and the biological activity of these compounds are described.
DIMETHYLALUMINIUM METHANESELENOLATE - A USEFUL REAGENT FOR THE PREPARATION OF SELENOESTERS. A NEW FRIEDEL-CRAFTS ACYLATION PROCEDURE PROMOTED BY Cu(I)
Kozikowski, Alan P.,Ames, Anthony
, p. 4821 - 4834 (2007/10/02)
The preparation of a new aluminium reagent, dimethylaluminium methaneselenolate (Me2AlSeMe) is described.The reactivity of this aluminium reagent toward a variety of organic substrates has been studied.Me2AlSeMe will convert O-alkyl esters to selenoesters in high yield.These selenoesters function as extremely reactive acyl transfer agents and are converted to acids, esters, and amides on reaction with water, alcohols or amines in the presence of a selenophilic metal cation.The selenoesters will, moreover, acylate reactive arenes and heterocyclic compounds when cuprous triflate is employed as the selenophilic metal cation.This latter transformation constitutes a new transition metal promoted variant of the Friedel-Crafts acylation reaction.
