Synthesis, and prediction of molecular properties and antimicrobial activity of some acylhydrazones derived from $N$-(arylsulfonyl)methionine

Authors

ESRA TATAR
SEVİL ŞENKARDEŞ
HASAN ERDİNÇ SELLİTEPE
ŞÜKRİYE GÜNİZ KÜÇÜKGÜZEL
ŞENGÜL ALPAY KARAOĞLU
ARİF BOZDEVECİ
ERIK DE CLERCQ
CHRISTOPHE PANNECOUQUE
TAİBİ BEN HADDA
İLKAY KÜÇÜKGÜZEL

DOI

10.3906/kim-1509-21

Abstract

A series of 38 new acylhydrazones [3-40], derived from (2$S)$-4-(methylsulfanyl)-2-[[(4-methylphenyl)sulfonyl] amino]butanoic acid hydrazide [2], were synthesized and evaluated for their anti-HIV and antimicrobial activity with the further aim to develop acylhydrazones carrying an amino acid side chain. All tested compounds possess stronger activity against gram (+) bacteria. Compound 23 was found active against methicillin-resistant Staphylococcus aureus (MRSA) with a MIC value of 3.9 $\mu $g/mL. The MIC value of compound 30 against Enterococcus faecalis, Listeria monocytogenes, and Bacillus cereus was 8 $\mu $g/mL. A computational study for prediction of ADME and drug-like properties (solubility, drug-likeness, and drug score) as well as potential toxicity profiles of compounds 2-40 was performed using the Molinspiration online property calculation toolkit and Osiris Property Explorer. As most of our compounds meet Lipinski's rule of five, they promise good solubility and permeability. According to Osiris calculations, the majority of our compounds are supposed to be nonmutagenic and nonirritating.

Keywords

Acylhydrazones, antimicrobial activity, $L$-methionine, microwave-assisted synthesis, MRSA

First Page

510

Last Page

534

Recommended Citation

TATAR, ESRA; ŞENKARDEŞ, SEVİL; SELLİTEPE, HASAN ERDİNÇ; KÜÇÜKGÜZEL, ŞÜKRİYE GÜNİZ; KARAOĞLU, ŞENGÜL ALPAY; BOZDEVECİ, ARİF; CLERCQ, ERIK DE; PANNECOUQUE, CHRISTOPHE; HADDA, TAİBİ BEN; and KÜÇÜKGÜZEL, İLKAY (2016) "Synthesis, and prediction of molecular properties and antimicrobial activity of some acylhydrazones derived from $N$-(arylsulfonyl)methionine," Turkish Journal of Chemistry: Vol. 40: No. 3, Article 13. https://doi.org/10.3906/kim-1509-21
Available at: https://journals.tubitak.gov.tr/chem/vol40/iss3/13