Synthesis and Biological Evaluation of New Schiff Bases Derived from 4-Amino-5-(3-fluorophenyl)-1,2,4-triazole-3-thione

被引：13

作者：

Janowska, Sara ^{[1
]}

Khylyuk, Dmytro ^{[1
]}

Janowski, Michal ^{[1
]}

Kosikowska, Urszula ^{[2
]}

Strzyga-Lach, Paulina ^{[3
]}

Struga, Marta ^{[3
]}

Wujec, Monika ^{[1
]}

机构：

[1] Med Univ, Fac Pharm, Dept Organ Chem, 4a Chodzki Str, PL-20093 Lublin, Poland

[2] Med Univ, Fac Pharm, Dept Pharmaceut Microbiol, 1 Chodzki Str, PL-20093 Lublin, Poland

[3] Fac Med, Chair & Dept Biochem, Banacha Str 1, PL-02097 Warsaw, Poland

来源：

MOLECULES | 2023年 / 28卷 / 06期

关键词：

synthesis; Schiff bases; antimicrobial activity; antifungal activity; cytotoxicity; docking studies; ANTIMICROBIAL EVALUATION; METAL-COMPLEXES; DOCKING; 1,3,4-THIADIAZOLES; DERIVATIVES; HYDRAZONES; BEARING; AGAR;

D O I：

10.3390/molecules28062718

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The treatment of infectious diseases is a challenging issue faced by the medical community. The emergence of drug-resistant strains of bacteria and fungi is a major concern. Researchers and medical professionals are working to develop new and innovative treatments for infectious diseases. Schiff bases are one a promising class of compounds. In this work, new derivatives were obtained of the 4-amino-5-(3-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione reaction, with corresponding benzaldehydes with various substituents at position 4. The antibacterial and antifungal activities of all synthesized compounds were tested. Several new substances have shown moderate antifungal activity against Candida spp. The highest activity directed against C. albicans was shown by compound RO4, with a 4-methoxyphenyl moiety and an MIC value of 62.5 mu g/mL. In order to check the toxicity of the synthesized compounds, their effect on cell lines was examined. Additionally, we tried to elucidate the mechanism of the antibacterial and antifungal activity of the tested compounds using molecular docking to topoisomerase IV, D-Alanyl-D-Alanine Ligase, and dihydrofolate reductase.

引用

页数：21

共 65 条

[1] Hybrid Pharmacophore Design, Molecular Docking, Synthesis, and Biological Evaluation of Novel Aldimine-Type Schiff Base Derivatives as Tubulin Polymerization Inhibitor [J].

Ameri, Alieh ;

Khodarahmi, Ghadamali ;

Forootanfar, Hamid ;

Hassanzadeh, Farshid ;

Hakimelahi, Gholam-Hosein .

CHEMISTRY & BIODIVERSITY, 2018, 15 (03)

[2] Pharmacomodulations of the benzoyl-thiosemicarbazide scaffold reveal antimicrobial agents targeting D-alanyl-D-alanine ligase in bacterio [J].

Ameryckx, Alice ;

Pochet, Lionel ;

Wang, Gang ;

Yildiz, Esra ;

Saadi, Bouazza Es ;

Wouters, Johan ;

Van Bambeke, Francoise ;

Frederick, Raphael .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 200

[3] Synthesis, Characterization and Antimicrobial Evaluation of Some New Schiff, Mannich and Acetylenic Mannich Bases Incorporating a 1,2,4-Triazole Nucleus [J].

Aouad, Mohamed R. .

MOLECULES, 2014, 19 (11) :18897-18910

[4]

Arulmurugan S., 2010, RASAYAN J. Chem, V3, P385

[5] Antifungal Susceptibility Testing: Current Approaches [J].

Berkow, Elizabeth L. ;

Lockhart, Shawn R. ;

Ostrosky-Zeichner, Luis .

CLINICAL MICROBIOLOGY REVIEWS, 2020, 33 (03)

[6]

Bihdan O, 2018, RES J PHARM BIOL CHE, V9, P166

[7] An Optimized Workflow for the Discovery of New Antimicrobial Compounds Targeting Bacterial RNA Polymerase Complex Formation [J].

Caputo, Alessia ;

Sartini, Sara ;

Levati, Elisabetta ;

Minato, Ilaria ;

Elisi, Gian Marco ;

Di Stasi, Adriana ;

Guillou, Catherine ;

Goekjian, Peter G. ;

Garcia, Pierre ;

Gueyrard, David ;

Bach, Stephane ;

Comte, Arnaud ;

Ottonello, Simone ;

Rivara, Silvia ;

Montanini, Barbara .

ANTIBIOTICS-BASEL, 2022, 11 (10)

[8] A Review on the Antimicrobial Activity of Schiff Bases: Data Collection and Recent Studies [J].

Ceramella, Jessica ;

Iacopetta, Domenico ;

Catalano, Alessia ;

Cirillo, Francesca ;

Lappano, Rosamaria ;

Sinicropi, Maria Stefania .

ANTIBIOTICS-BASEL, 2022, 11 (02)

[9] Synthesis of Schiff bases modified inulin derivatives for potential antifungal and antioxidant applications [J].

Chen, Yuan ;

Mi, Yingqi ;

Li, Qing ;

Dong, Fang ;

Guo, Zhanyong .

INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2020, 143 :714-723

[10]

Clinical and Laboratory Standards Institute, 2015, Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically-tenth edition: approved standard M07-A10

← 1 2 3 4 5 6 7 →