96719-55-0Relevant articles and documents
Antiimplantation Agents: Part II - 1,2-Diaryl-1,2,3,4-tetrahydroisoquinolines
Nagarajan, K.,Talwalker, P. K.,Kulkarni, C. L.,Shah, R. K.,Shenoy, S. J.,Prabhu, S. S.
, p. 83 - 97 (2007/10/02)
1,2-Diaryl-3,4-dihydroisoquinolinium derivatives (5) have been synthesised from N-aryl-N-aroyl-β-phenethylamines (4) and found to exhibit no antiimplantation activity in the rat whereas many of the corresponding tetrahydroisoquinolines (6) are active.Structure-activity relationships have also been studied. 1-(p-Fluorophenyl)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroisoquinoline (6u) and its nor derivative (6v) are very potent, while the ortho (6g) and the meta (6n) fluoro analogues as well as the des-fluoro derivative (6d) are quite active.Extensive biological tests have been carried out on 6g.The enantiomers (+)-6p*HCl and (-)-6q*HCl of 6n have similar activity profiles as that of 6n showing no separation of antiimplantation and estrogenic properties.Diastereomeric 2-(2-methyl-2-phenethyl)-1-phenyl-1,2,3,4-tetrahydroisoquinolines (13a and 13b) show similar properties, while the tetracyclic derivative 19 is inactive. 2-Phenoxyethyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline (26) shows moderate activity, but 1-(β-phenethyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 29 is inactive.
