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Synthesis, DFT Study, and Antitumor Activity of Some New Heterocyclic Compounds Incorporating Isoxazole Moiety
Author(s) -
Hamama Wafaa S.,
Ibrahim Mona E.,
Zoorob Hanafi H.
Publication year - 2017
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201700064
Subject(s) - chemistry , isoxazole , moiety , derivative (finance) , annulation , alkylation , benzene , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , financial economics , economics
Thiazolidin‐4‐one derivative 3 was synthesized by the transformation of chloroacetamide derivative 2 with NH 4 SCN.The condensation of 3 with p ‐anisaldehyde afforded the corresponding arylidene derivative 4 . Also, the alkylation of chloroacetamide derivative 2 with different heterocyclic compounds was investigated. Annulation of 5‐amino‐3‐methylisoxazole ( 1 ) with α‐halocarbonyl compounds 12 and 14 furnished pyrrolo[3,2‐d]isoxazole and isoxazolo[5,4‐b]azepin‐6‐one derivatives 13 and 15 , respectively, while reaction of 1 with 1‐chloro‐4‐(chloromethyl)benzene gave the monoalkylated product 17 . The newly synthesized compounds were screened for their antitumor activity, and the geometry optimizations are in a good agreement with the experimentally observed data.