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Synthesis of chloro, fluoro, and nitro derivatives of 7‐amino‐5‐aryl‐6‐cyano‐5 H ‐pyrano pyrimidin‐2,4‐diones using organic catalysts and their antimicrobial and anticancer activities
Author(s) -
Aremu Oluwole S.,
Singh Parvesh,
Singh Moganavelli,
Mocktar Chunderika,
Koorbanally Neil A.
Publication year - 2019
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.3695
Subject(s) - chemistry , dabco , malononitrile , catalysis , nitro , aryl , barbituric acid , medicinal chemistry , derivative (finance) , antimicrobial , organic chemistry , alkyl , financial economics , economics
Abstract Chloro, fluoro, and nitro derivatives of 7‐amino‐5‐aryl‐6‐cyano‐5 H ‐pyrano pyrimidin‐2,4‐diones were produced by reacting malononitrile, barbituric acid, and aromatic aldehydes together with a DABCO catalyst in an aqueous one‐pot reaction. This is the first report of these compounds being synthesized with DABCO as a catalyst, which produced the compounds in yields in excess of 90%. The 2,4‐difluoro derivative ( 11 ) was novel. The structures of the synthesized compounds were elucidated by means of 1 H, 13 C, and 2D NMR spectroscopy. Compound 2 (2‐Cl derivative) had MBC values of <200μM against both Staphylococcus aureus and MRSA, and the 2‐nitro derivative 5 had an MBC of 191μM against the Gram–ve E scherichia coli . The synthesized compounds were also tested for their anticancer activity against a HeLa cell line, where all the compounds showed better activity (IC 50 values between 129μM and 340μM) than 5‐fluorouracil, a commonly known anticancer drug.