1. Synthesis, and prediction of molecular properties and antimicrobial activity of some acylhydrazones derived from $N$-(arylsulfonyl)methionine
- Author
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Şükriye Küçükgüzel, Sevil Şenkardeş, Erik De Clercq, Hasan Erdinç Sellitepe, Şengül Alpay Karaoğlu, Christophe Pannecouque, Arif Bozdeveci, Taibi Ben Hadda, Esra Tatar, İlkay Küçükgüzel, Tatar, Esra, Senkardes, Sevil, Sellitepe, Hasan Erdinc, Kucukguzel, Sukriye Guniz, Karaoglu, Sengul Alpay, Bozdeveci, Arif, De Clercq, Erik, Pannecouque, Christophe, Ben Hadda, Taibi, Kucukguzel, Ilkay, RTEÜ, Fen - Edebiyat Fakültesi, Biyoloji Bölümü, and Karaoğlu, Şengül Alpay
- Subjects
BIOLOGICAL-ACTIVITIES ,Bacillus cereus ,MRSA ,Antimicrobial activity ,010402 general chemistry ,Hydrazide ,ANTIFUNGAL ACTIVITY ,01 natural sciences ,Enterococcus faecalis ,microwave-assisted synthesis ,Microwave-assisted synthesis ,HYDRAZIDE DERIVATIVES ,chemistry.chemical_compound ,HIV-1 REVERSE-TRANSCRIPTASE ,RIBONUCLEASE-H ,Solubility ,L-methionine ,ADME ,Acylhydrazones ,Sulfonyl ,chemistry.chemical_classification ,antimicrobial activity ,biology ,N-ACYLHYDRAZONES ,010405 organic chemistry ,ANTI-HIV ,General Chemistry ,ANTIVIRAL EVALUATION ,biology.organism_classification ,Antimicrobial ,Combinatorial chemistry ,0104 chemical sciences ,chemistry ,Lipinski's rule of five ,PROTEIN SYNTHASE III ,COLORIMETRIC ASSAY ,Acylhydrazones,antimicrobial activity,$L$-methionine,microwave-assisted synthesis,MRSA - Abstract
Sellitepe, Hasan Erdinc/0000-0001-5339-6940; Pannecouque, Christophe/0000-0002-1254-4473; Tatar, Esra/0000-0003-3490-8597; Kucukguzel, Ilkay/0000-0002-7188-1859; senkardes, sevil/0000-0002-0523-459X; BOZDEVECI, ARIF/0000-0002-0729-9143 WOS: 000376305300013 A series of 38 new acylhydrazones [3-40], derived from (2S)-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. Research Fund of Marmara UniversityMarmara University [SAG-A-060510-0109] This work was supported by the Research Fund of Marmara University, project number: SAG-A-060510-0109.
- Published
- 2016