Chemoselective Synthesis of N-(Aminoalkyl/amidino)phenyl Naphthalene-1-carboxamides and 5,6,7,8-Tetrahydronaphthalene-1-carboxamides and Their Anticoagulant Screening

Abstract

N-[(Aminoalkyl)phenyl]-1-naphthamides and N-[(amino­alkyl)phenyl]-5,6,7,8-tetrahydronaphthalene-1-carboxamides were selectively synthesized from the corresponding cyanonaphthamides by catalytic hydrogenation. N-(Amidinophenyl)-1-naphthalenecarbox­amides and N-(amidinophenyl)-5,6,7,8-tetrahydronaphthalene-1-carboxamides were chemoselectively obtained from the corresponding O-acetylamidoximes or amidoximes, respectively, by catalytic hydrogenation. The products were screened for their anticoagulant effects in human plasma, as measured by the activated partial thromboplastin time and the prothrombin time in vitro. Amidines and 5,6,7,8-tetra­hydronaphthamides were more active than aminoalkyl compounds and naphthamides.