Molecules, Vol. 23, Pages 1724: Asymmetric Primaquine and Halogenaniline Fumardiamides as Novel Biologically Active Michael Acceptors
Molecules, Vol. 23, Pages 1724: Asymmetric Primaquine and Halogenaniline Fumardiamides as Novel Biologically Active Michael Acceptors
Molecules doi: 10.3390/molecules23071724
Authors:
Zrinka Rajić
Maja Beus
Hana Michnová
Josipa Vlainić
Leentje Persoons
Ivan Kosalec
Josef Jampílek
Dominique Schols
Toma Keser
Branka Zorc
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 Mycobacter...
Source: Molecules - Category: Chemistry Authors: Zrinka Raji ć Maja Beus Hana Michnov á Josipa Vlaini ć Leentje Persoons Ivan Kosalec Josef Jamp ílek Dominique Schols Toma Keser Branka Zorc Tags: Article Source Type: research
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