Literature DB >> 35164333

Synthesis, Biological Evaluation and Molecular Docking Studies of 5-Indolylmethylen-4-oxo-2-thioxothiazolidine Derivatives.

Volodymyr Horishny1, Athina Geronikaki2, Victor Kartsev3, Vasyl Matiychuk4, Anthi Petrou2, Pavel Pogodin5, Vladimir Poroikov5, Theodora A Papadopoulou6, Ioannis S Vizirianakis6,7, Marina Kostic8, Marija Ivanov8, Marina Sokovic8.   

Abstract

BACKGROUND: Infectious diseases represent a significant global strain on public health security and impact on socio-economic stability all over the world. The increasing resistance to the current antimicrobial treatment has resulted in the crucial need for the discovery and development of novel entities for the infectious treatment with different modes of action that could target both sensitive and resistant strains.
METHODS: Compounds were synthesized using the classical organic chemistry methods. Prediction of biological activity spectra was carried out using PASS and PASS-based web applications. Pharmacophore modeling in LigandScout software was used for quantitative modeling of the antibacterial activity. Antimicrobial activity was evaluated using the microdilution method. AutoDock 4.2® software was used to elucidate probable bacterial and fungal molecular targets of the studied compounds.
RESULTS: All compounds exhibited better antibacterial potency than ampicillin against all bacteria tested. Three compounds were tested against resistant strains MRSA, P. aeruginosa and E. coli and were found to be more potent than MRSA than reference drugs. All compounds demonstrated a higher degree of antifungal activity than the reference drugs bifonazole (6-17-fold) and ketoconazole (13-52-fold). Three of the most active compounds could be considered for further development of the new, more potent antimicrobial agents.
CONCLUSION: Compounds 5b (Z)-3-(3-hydroxyphenyl)-5-((1-methyl-1H-indol-3-yl)methylene)-2-thioxothiazolidin-4-one and 5g (Z)-3-[5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxo-thiazolidin-3-yl]-benzoic acid as well as 5h (Z)-3-(5-((5-methoxy-1H-indol-3-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)benzoic acid can be considered as lead compounds for further development of more potent and safe antibacterial and antifungal agents.

Entities:  

Keywords:  4-oxo-2-thioxothiazolidine; CYP51; MurB; antibacterial; antifungal; biological activity prediction; docking; microdilution method

Mesh:

Substances:

Year:  2022        PMID: 35164333      PMCID: PMC8839324          DOI: 10.3390/molecules27031068

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  54 in total

1.  Synthesis of novel 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties as potential antibacterial agents.

Authors:  Li-Li Xu; Chang-Ji Zheng; Liang-Peng Sun; Jing Miao; Hu-Ri Piao
Journal:  Eur J Med Chem       Date:  2011-12-13       Impact factor: 6.514

2.  Quinazolinone-based rhodanine-3-acetic acids as potent aldose reductase inhibitors: Synthesis, functional evaluation and molecular modeling study.

Authors:  Sherihan El-Sayed; Kamel Metwally; Abdalla A El-Shanawani; Lobna M Abdel-Aziz; Ahmed A El-Rashedy; Mahmoud E S Soliman; Luca Quattrini; Vito Coviello; Concettina la Motta
Journal:  Bioorg Med Chem Lett       Date:  2017-08-24       Impact factor: 2.823

3.  Kinetic characterization of wild-type and S229A mutant MurB: evidence for the role of Ser 229 as a general acid.

Authors:  T E Benson; C T Walsh; V Massey
Journal:  Biochemistry       Date:  1997-01-28       Impact factor: 3.162

4.  Synthesis and antimicrobial evaluation of L-phenylalanine-derived C5-substituted rhodanine and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone.

Authors:  Xin Jin; Chang-Ji Zheng; Ming-Xia Song; Yan Wu; Liang-Peng Sun; Yin-Jing Li; Li-Jun Yu; Hu-Ri Piao
Journal:  Eur J Med Chem       Date:  2012-08-27       Impact factor: 6.514

Review 5.  [Computer-aided drug design: from discovery of novel pharmaceutical agents to systems pharmacology].

Authors:  V V Poroikov
Journal:  Biomed Khim       Date:  2020-01

6.  Exploring Anti-inflammatory Potential of Thiazolidinone Derivatives of Benzenesulfonamide via Synthesis, Molecular Docking and Biological Evaluation.

Authors:  Sanjay B Bari; Sandip D Firake
Journal:  Antiinflamm Antiallergy Agents Med Chem       Date:  2016

7.  Uncovering the pharmacological response of novel sesquiterpene derivatives that differentially alter gene expression and modulate the cell cycle in cancer cells.

Authors:  Melpomeni G Akrivou; Vera P Demertzidou; Nikoleta F Theodoroula; Fani M Chatzopoulou; Konstantinos A Kyritsis; Nikolaos Grigoriadis; Alexandros L Zografos; Ioannis S Vizirianakis
Journal:  Int J Oncol       Date:  2018-09-03       Impact factor: 5.650

8.  Potent BACE-1 inhibitor design using pharmacophore modeling, in silico screening and molecular docking studies.

Authors:  Shalini John; Sundarapandian Thangapandian; Sugunadevi Sakkiah; Keun Woo Lee
Journal:  BMC Bioinformatics       Date:  2011-02-15       Impact factor: 3.169

Review 9.  The antimicrobial resistance crisis: causes, consequences, and management.

Authors:  Carolyn Anne Michael; Dale Dominey-Howes; Maurizio Labbate
Journal:  Front Public Health       Date:  2014-09-16

10.  Synthesis and Bioactivity Evaluation of N-Arylsulfonylindole Analogs Bearing a Rhodanine Moiety as Antibacterial Agents.

Authors:  Ming-Xia Song; Song-Hui Li; Jiao-Yang Peng; Ting-Ting Guo; Wen-Hui Xu; Shao-Feng Xiong; Xian-Qing Deng
Journal:  Molecules       Date:  2017-06-14       Impact factor: 4.411

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