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Synthesis and In Vitro Antitumor Activity of New Isoxazolo[5,4‐d]Pyrimidine Systems
Author(s) -
Hamama Wafaa S.,
Ibrahim Mona E.,
Zoorob Hanafi H.
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2521
Subject(s) - chemistry , aldimine , benzylamine , pyrimidine , methylamine , isatin , amine gas treating , mannich reaction , derivative (finance) , stereochemistry , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , financial economics , economics
The reaction of 5‐amino‐3‐methylisoxazole ( 1 ) with aldimines 2 , 3 , 4 , 5 , 6 , 7 gave basic side chain 5‐amino‐3‐methylisoxazole derivatives 8 , 9 , 10 , 11 , 12 , 13 . Annulations of derivatives 8 , 9 , 10 , 11 , 12 , 13 with anisaldehyde afforded the target isoxazolo[5,4‐ d ]pyrimidines 14 , 15 , 16 , 17 . Treatment of 1 with isatin ketimine anil 18 resulted in the formation of derivative 19 , which further cyclized with anisaldehyde afforded the spirotetracyclic system 20 . Mannich reaction of 1 with primary amine such as methylamine and benzylamine gave the corresponding isoxazolo[5,4‐d]pyrimidine derivatives 21 and 22 , respectively. The newly synthesized compounds were tested for their antitumor activity.