Synthesis, molecular docking and QSAR studies of 2, 4-disubstituted thiazoles as antimicrobial agents

Arora, Preeti; Narang, Rakesh; Bhatia, Sonam; Nayak, Satheesha B; Singh, Sachin Kumar; Narasimhan, Balasubramanian

doi:10.7324/japs.2015.50206

Cited by 28 publications

(16 citation statements)

References 58 publications

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“…The activity data for all compounds were taken from different scientific groups in terms of inhibitory activity (MIC μg/ml) (Jasmine et al, 2012; Shruthi et al, 2012; Jayanna et al, 2013; Hareesh et al, 2015; Preeti et al, 2015; Talavara et al, 2016). Fifty compounds out of hundred, were selected as a training set based following criteria that will produce a good quantitative structural activity relationship (QSAR) model.…”

Section: Methodsmentioning

confidence: 99%

Angular Phenozaxine Ethers as Potent Multi-microbial Targets Inhibitors: Design, Synthesis, and Molecular Docking Studies

Ezeokonkwo

Ogbonna²,

Okafor

et al. 2017

Front. Chem.

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The reaction of diaza-5H-benzo[a]phenoxazin-5-one and 5H-benzo[a]phenoxazin-5-one with various phenols catalyzed by Pd/t-BuXPhos/K3PO4 system gave previously unknown ether derivatives (7a–f and 8a–f) in good yields. UV-visible, FTIR, and 1H NMR data were used to confirm structures of the synthesized compounds. The parent compounds and the derivatives were screened in-silico for their drug-likeness and binding affinities to the microbial targets through molecular docking. Molinspiration software and AutoDock were used for the drug-likeness and docking studies, respectively. All the synthesized compounds showed strong drug-likeness. They also showed excellent binding affinities with glucosamine-6-phosphate synthase (2VF5), AmpC beta-lactamase (1KE4), and Lanosterol-14α-demethylase (3JUV), with compound 7e having the highest binding energies −9.5, −9.3, and −9.3 kcal/mol, respectively. These were found to be higher than the binding energies of the standard drugs. The binding energies of ciprofloxacin with 2VF5 and 1KE4 were −7.8 and −7.5 kcal/mol, respectively, while that of ketoconazole with 3JUV was −8.6 kcal/mol. The study showed that the synthesized compounds have multi-target inhibitory effects and can be very useful in multi-drug resistance cases. A 2D quantitative structural activity relationship (QSAR) model against target Glucosamine-6-phosphate synthase (2VF5) was developed using partial least squares regression (PLS) with good internal prediction (R2 = 0.7400) and external prediction (R2_ predicted = 0.5475) via Molecular Operating Environment (2014).

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Section: Methodsmentioning

confidence: 99%

Angular Phenozaxine Ethers as Potent Multi-microbial Targets Inhibitors: Design, Synthesis, and Molecular Docking Studies

Ezeokonkwo

Ogbonna²,

Okafor

et al. 2017

Front. Chem.

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“…The highest activity showed by T3 might be due to the presence of electron donating group which is methoxy (OCH 3 ), which enhance its interaction towards the tested bacteria. Incorporation of methoxy group in the thiazole compound has boosted the antimicrobial activity in terms of increase in lipophilicity behavior that easily penetrated into the membrane of bacterial strains [29]. Besides, methoxy group also provides electron donating behaviour which enhanced the overall antibacterial activity of the synthesized compound [30].…”

Section: Antibacterial Activitiesmentioning

confidence: 99%

Synthesis and Molecular Docking of 2,4,5-Trisubstituted-1,3-Thiazole Derivatives as Antibacterial Agents

2019

MJAS

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The emergence of antibiotic resistance against bacterial strains has attracted great interest in the discovery and development of new antibacterial agents. Thiazole derivatives have been widely used in the biological as well as pharmacological fields and their efficiency as pharmaceutical drugs are well established. In this study, a series of thiazole derivatives were synthesized in reaction between 3-chloroacetyl acetone and ammonium thiocyanate followed by incorporating selected amines in one-pot synthesis manner. The compounds were structurally characterized by Fourier Transform Infrared (FTIR), Proton Nuclear Magnetic Resonance ( 1 H NMR), Ultraviolet-Visible (UV-Vis) and Gas Chromatography-Mass Spectrometry (GC-MS). Their antibacterial properties were screened using disc diffusion technique against selected Gram-positive (Bacillus cereus and Staphylococcus epidermidis) as well as Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) with T3 exhibited the most potent antibacterial activity. Molecular docking studies were also performed against Glucosamine-6-phosphate (GlcN-6-P) synthase which is known as the essential building block of most bacteria. The docking result displayed that T3 exhibited the minimum binding energy of -7.09 kcal mol -1 as compared to T1 and T2 with -6.49 and -6.76 kcal mol -1 , respectively which is in agreement with antibacterial result. The output of this preliminary study will contribute in structural enhancement in drug discovery. AbstrakKewujudan rintangan terhadap bakteria telah menarik minat dalam penemuan dan perkembangan agen antibakteria yang terkini. Terbitan tiazol telah digunakan dengan meluas dalam bidang biologi dan farmakologi di mana keberkesanannya sebagai ubat farmaseutikal telah ditemui. Dalam kajian ini, terbitan tiazol telah disintesis dengan menindakbalaskan α-haloketon (3-kloroasetil aseton), ammonium tiosianat dan beberapa sebatian amina terpilih secara sintesis satu pot. Produk tindak balas yang terhasil telah dicirikan dengan Transformasi Fourier-Inframerah (FTIR), Proton Resonans Magnet Nukleus ( 1 H NMR), Ultralembayung-Sinar Nampak (UV-Vis) serta Kromatografi Gas-Spektrometer Jisim (GC-MS). Sifat antibakteria sebatian ini telah disaring menggunakan teknik serapan cakera terhadap bakteria Gram-positif (Bacillus cereus dan Staphylococcus epidermidis) dan Gram-negatif (Escherichia coli dan Pseudomonas aeruginosa) dengan T3 menunjukkan aktiviti antibakteria yang paling berkesan. Penyatuan molekul telah dilakukan terhadap enzim Glukosamina-6-fosfat sintase (GlcN-6-P) yang merupakan unsur binaan penting bagi kebanyakan bakteria. Merujuk kepada keputusan penyatuan molekul, T3 menunjukkan tenaga pengikatan yang paling minima iaitu -7.09 kcal mol -1 berbanding T1 dan T2 masing-masing pada -6.49 dan -6.76 kcal mol -1 , menunjukkan nilai-nilai ini bersetuju dengan keputusan saringan antibakteria. Keputusan kajian awal ini akan menyumbang kepada penambahbaikan struktur untuk penghasilan ubat.

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“…Narang and coworkers reported 2,4‐disubstituted thiazole derivatives from 2‐amino‐4‐phenylthiazole and screened them against B. subtilis , E. coli , S. aureus , A. niger and C. albicans for antimicrobial effectiveness in reference to Ciprofloxacin and Fluconazole. Complementing with molecular docking study outcomes, enhanced activity was observed by methoxy group (MIC 4.49‐4.60 μm/mL) inclusion at para position of phenyl ring ( 55 ).…”

Section: Introductionmentioning

confidence: 99%

A retrospect on antimicrobial potential of thiazole scaffold

Mishra

Mujwar

et al. 2020

Journal of Heterocyclic Chem

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Due to its appreciable diversity in biological actions, thiazole and its substituted components, a significant class of heterocyclic compounds has developed as an influential scaffold in the field of chemical sciences. The variability of thiazole core has been expressed through the effective instigation of its anticancer (Dasatinib, Tiazofurin), antiretroviral (Ritonavir, Brecanavir), antimicrobial (Sulfathiazole, Ravuconazole) and anti-inflammatory (Fenclozic acid, Meloxicam) derivatives. This reasonable diversity in the physiological reaction pattern led many scientists to refine and develop new structural alternatives with much more efficient pharmacological action. This review is crucial for previous studies and projects to survey the antimicrobial activity of thiazole and thiazole related compounds to the mid of 2019.

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Synthesis, molecular docking and QSAR studies of 2, 4-disubstituted thiazoles as antimicrobial agents

Cited by 28 publications

References 58 publications

Angular Phenozaxine Ethers as Potent Multi-microbial Targets Inhibitors: Design, Synthesis, and Molecular Docking Studies

Angular Phenozaxine Ethers as Potent Multi-microbial Targets Inhibitors: Design, Synthesis, and Molecular Docking Studies

Synthesis and Molecular Docking of 2,4,5-Trisubstituted-1,3-Thiazole Derivatives as Antibacterial Agents

A retrospect on antimicrobial potential of thiazole scaffold

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