Synlett
DOI: 10.1055/s-0036-1588517
letter
© Georg Thieme Verlag Stuttgart · New York

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

Thi Ha Nguyena, b, Eunsook Ma*a
  • aCollege of Pharmacy, Catholic University of Daegu, Hayang-ro 13-13, Hayang-eup, Gyeongsan-si, Gyeongbuk 712-702, Republic of Korea   Email: masook@cu.ac.kr
  • bDepartment of Phytochemistry, National Institute of Medicinal Materials (NIMM), Hanoi 100000, Vietnam
This 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)
Further Information

Publication History

Received: 13 May 2017

Accepted after revision: 03 July 2017

Publication Date:
08 August 2017 (eFirst)

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.

Supporting Information