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Synthesis and Biological Evaluation of Some Novel Isoxazole Derivatives
Author(s) -
Hamama W. S.,
Ibrahim M. E.,
Zoorob H. H.
Publication year - 2017
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.2589
Subject(s) - isoxazole , chemistry , alkylation , pyridine , mannich reaction , derivative (finance) , hydrochloride , imidazole , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , financial economics , economics
The reaction of 5‐amino‐3‐methylisoxazole ( 1 ) with formalin and secondary amines gave the corresponding Mannich bases 3 , 4 , 5 , 6 . Alkylation of isoxazole derivative 1 with Mannich bases hydrochloride gave unsubstituted isoxazolo[5,4‐ b ]pyridine derivatives 8a , 8b via alkylation at position 4. Moreover, coupling reaction of 1 with different diazonium salts gave the corresponding mono and bisazo dyes of isoxazole derivative. The newly synthesized compounds were screened for their antitumor activity compared with 5‐fluorouracil as a well‐known cytotoxic agent using Ehrlich ascites carcinoma cells. Interestingly, the obtained results showed clearly that compounds 3 , 15 , 8b , 4 , 8a , and 5 exhibited high antitumor activity than 5‐fluorouracil.