Chemoselective Synthesis of N-(Aminoalkyl/amidino)phenyl Naphthalene-1-carboxamides and 5,6,7,8-Tetrahydronaphthalene-1-carboxamides and Their Anticoagulant ScreeningThis research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), funded by the Ministry of Education, Science, and Technology (2010-0013516)
Received: 13 May 2017
Accepted after revision: 03 July 2017
08 August 2017 (eFirst)
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.