87307-82-2Relevant academic research and scientific papers
Synthesis of enantiopure 10-nornaltrexones in the search for toll-like receptor 4 antagonists and opioid ligands
Selfridge, Brandon R.,Deschamps, Jeffrey R.,Jacobson, Arthur E.,Rice, Kenner C.
, p. 5007 - 5018 (2014/06/23)
10-Nornaltrexones (3-(cyclopropylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6- hexahydro-1H-benzofuro[3,2-e]isoquinolin-7(7aH)-one, 1) have been underexploited in the search for better opioid ligands, and their enantiomers have been unexplored. The synthesis of tr
Synthesis and Opioid Activity of 7-Oxygenated 2,3,4,4a,5,6,7,7a-Octahydro-1H-benzofuroisoquinolin-9-ols
Cheng, Chen-Yu,Hsin, Ling-Wei,Tsai, Ming-Cheng,Shmidt, William K.,Smith, Christine,Tam, S. William
, p. 3121 - 3127 (2007/10/02)
3-(Cyclopropylmethyl)-9-hydroxy-7-oxo-2,3,4,4aα,5,6,7,7aα-octahydro-1H-benzofuroisoquinoline (4b) containing the ACNO ring system of morphine and a 7-keto function on ring C has been synthesized and found to possess potent PQW (ED50 = 0.15 mg/kg sc
Synthesis of 3-Methyl-5,6-dihydro-3H-benzofuroisoquinolin-7(7aH)-ones
Weller, Dwight D.,Stirchak, Eugene P.,Weller, Doreen L.
, p. 4597 - 4605 (2007/10/02)
The coupling of 2-(alkoxymethoxy)phenylcopper derivatives with the salt of ethyl chloroformate and ethyl 3-(pyridin-3-yl)propenoate was found to be an efficient method for the preparation of 4-(2-hydroxyphenyl)pyridines 13 substituted at C-3 with a propanoate side chain.N-Methylation and O-alkylation with ethyl bromoacetate gave salts 3 which when treated with base underwent an intramolecular enolate addition to the pyridinium nucleus to produce spiro 4.Prolonged base treatment of 4 yielded ethyl 3-methyl-7-hydroxy-5,7a-dihydro-3H-benzofuroisoquinoline-6-carboxylates 5 by a Dieckmann reaction.Reduction of 5 led to predominately trans-3-methylhexahydro-1H-benzofuroisoquinolin-7(7aH)-ones, while reduction of 4 and then Dieckmann cyclization yielded mainly the cis isomers.
