Asymmetric Primaquine and Halogenaniline Fumardiamides as Novel Biologically Active Michael Acceptors

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Zrinka RajićBranka Zorc

Abstract

Novel primaquine (PQ) and halogenaniline asymmetric fumardiamides 4a⁻f, potential Michael acceptors, and their reduced analogues succindiamides 5a⁻f were prepared by simple three-step reactions: coupling reaction between PQ and mono-ethyl fumarate (1a) or mono-methyl succinate (1b), hydrolysis of PQ-dicarboxylic acid mono-ester conjugates 2a,b to corresponding acids 3a,b, and a coupling reaction with halogenanilines. 1-[bis(Dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) was used as a coupling reagent along with Hünig's base. Compounds 4 and 5 were evaluated against a panel of bacteria, several Mycobacterium strains, fungi, a set of viruses, and nine different human tumor cell lines. p-Chlorofumardiamide 4d showed significant activity against Staphylococcus aureus,Streptococcus pneumoniae and Acinetobacter baumannii, but also against Candida albicans (minimum inhibitory concentration (MIC) 6.1⁻12.5 µg/mL). Together with p-fluoro and p-CF₃ fumardiamides 4b,f, compound 4d showed activity against Mycobacterium marinum and 4b,f against M. tuberculosis. In biofilm eradication assay, most of the bacteria, particularly S. aureus, showed susceptibility to fumardiamides. m-CF₃ and m-chloroa...Continue Reading

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Citations

Aug 4, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Maja BeusBranka Zorc
Oct 13, 2020·Molecular Diversity·Ivana PerkovićBranka Zorc
Oct 23, 2019·Acta Pharmaceutica : a Quarterly Journal of Croatian Pharmaceutical Society and Slovenian Pharmaceutical Society, Dealing with All Branches of Pharmacy and Allied Sciences·Branka ZorcIvana Perković
Jul 2, 2019·Acta Pharmaceutica : a Quarterly Journal of Croatian Pharmaceutical Society and Slovenian Pharmaceutical Society, Dealing with All Branches of Pharmacy and Allied Sciences·Maja BeusBranka Zorc

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Methods Mentioned

BETA
amidation
column chromatography
column
NMR
Assay

Software Mentioned

Chemicalize
GraphPad Prism
Waters MassLynx
. org

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