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Substituted adamantylphthalimides: Synthesis, antiviral and antiproliferative activity
Author(s) -
Mandić Leo,
Benčić Patricia,
MlinarićMajerski Kata,
Liekens Sandra,
Snoeck Robert,
Andrei Graciela,
Kralj Marijeta,
Basarić Nikola
Publication year - 2020
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.202000024
Subject(s) - phthalimide , adamantane , chemistry , substituent , moiety , stereochemistry , chemical synthesis , selectivity , structure–activity relationship , in vitro , biochemistry , organic chemistry , catalysis
In this study, three groups of adamantylphthalimides, bearing different substituents at the phthalimide moiety, N ‐(4′‐R 2 )phthalimidoadamantanes ( 1 – 7 ), 3‐[ N ‐(4′‐R 2 )phthalimido]‐1‐adamantanols ( 8 – 10 ), and 3‐[ N ‐(4′‐R 2 )phthalimido]adamantane‐1‐carboxylic acids ( 11 – 15 ), were synthesized and screened against tumor cells and viruses. The most potent compounds are not substituted at the adamantane and bear an OH or NH 2 substituent at the phthalimide (compounds 3 and 5 ). The antiproliferative activities of compounds 3 and 5 are in the micromolar range, much higher than the one of thalidomide. A minor antiviral activity against cytomegalovirus and varicella‐zoster virus was found for compounds 3 and 5 , but these compounds lacked selectivity. The results presented are important for the rational design of the next‐generation compounds with anticancer and antiviral activities.