Bourlot A S, Sánchez I, Dureng G, Guillaumet G, Massingham R, Monteil A, Winslow E, Pujol M D, Mérour J Y
Institut de Chimie Organique et Analytique associé au CNRS, Université d'Orléans, BP 6759, 45067 Orléans Cedex 2, France.
J Med Chem. 1998 Aug 13;41(17):3142-58. doi: 10.1021/jm970795t.
Substituted 1,4-benzoxazines bearing an amino side chain at the 2-position were prepared and were found to have a moderate activity on intracellular calcium. Of the compounds studied it was found that those which possess a homoveratrylamino moiety exhibited superior potency. The chain length and the nature of the amine (4-fluorophenylpiperazine, 4-fluorobenzhydryloxyethylamine, N-substituted homoveratrylamine) is discussed. The 4-benzyl-3, 4-dihydro-2-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-2H-1, 4-benzoxazine (3c) is the most potent derivative of the series with a ratio of IC50 values against PE (phenylephrine) and K+ of 2.1. Under these test conditions a ratio near 1 indicates potential intracellular calcium activity while a ratio greater than 100 an action on extracellular calcium influx.
