57399-32-3Relevant academic research and scientific papers
Synthesis of 4-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one, a key synthon for etretinate and its metabolites
Ashok, K.,Rao, G.S. Krishna
, p. 1013 - 1017 (2007/10/02)
A synthetic route to 4-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one (2), a valuable synthon to etretinate (1), a potent antipsoriatic drug is described.The keto acids (3a) and (3b) obtained from 2,5-dimethylanisole by acylation with methylsuccinic and succinic anhydrides, respectively are elaborated separately to the identical methoxytrimethyldihydronaphthalene (7a) which on ozonolysis furnishes the ring opened arylketoaldehyde (8).Strategic manipulation of the keto and aldehyde functions of 8 leads to the arylbutanone (14).Side chain bromination of 14 gives the bromoketone (15) which provides on dehydrobromination the key synthon (2).
Dihydroretinoic acids and their derivatives. Synthesis and biological activity
Pawson,Cheung,Han,Trown,Buck,Hansen,Bollag,Ineichen,Pleil,Rueegg
, p. 918 - 925 (2007/10/12)
The syntheses of the ring and four side-chain dihydroretinoic acids and/or their esters, 3-7, are described. The syntheses of several other retinoids containing a substituted aromatic ring are also included. The biological activity of the compounds was evaluated in vivo in a chemically induced mouse skin papilloma test and in vitro in two vitamin A deficient assays. The activity observed for 1a, 1c, and 2a in the former test was partially retained in the dihydro derivatives 4b, 4c, and 6b. Similar results were found in the in vitro assays.
