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Efficient MW‐Assisted Synthesis of Some New Isoquinolinone Derivatives With In Vitro Antitumor Activity
Author(s) -
Hekal Mohamed H.,
Abu ElAzm Fatma S. M.
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.2916
Subject(s) - chemistry , isoquinoline , acetic anhydride , in vitro , anthranilic acid , nucleophile , microwave irradiation , combinatorial chemistry , organic chemistry , biochemistry , catalysis
An efficient and convenient synthesis of novel [1,3]oxazino[3,2‐b]isoquinoline‐5,12‐dione derivative 4 was achieved by the reaction of anthranilic acid with homophthalic anhydride under microwave irradiation, followed by cyclization with acetic anhydride. Some new isoquinolinone and fused isoquinolinone derivatives were prepared via reaction of compound 4 with different nitrogen nucleophiles by using reflux and a focused microwave reactor. Microwave irradiation favored the formation of the desired products with improved yields and shortened reaction times. This is a simple and green method for the synthesis of isoquinolinone derivatives. The structures of the prepared compounds were elucidated by IR, 1 H‐NMR, and mass spectroscopy. Some of the newly prepared compounds were tested in vitro against a panel of three human tumor cell lines, namely, hepatocellular carcinoma (liver) HepG2, colon cancer HCT‐116, and mammary gland breast MCF‐7. Almost all of the tested compounds showed satisfactory activity.