Design, Synthesis, Antibacterial Evaluation and Molecular Docking Studies of Some Newer Baenzothiazole Containing Aryl and Alkaryl Hydrazides

Gurram, Swarupa Rani; Azam, Mohammed Afzal

doi:10.1002/cbdv.202100117

Cited by 5 publications

(1 citation statement)

References 41 publications

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“…In 2021, Gurram et al 81 reported 27 novel benzothiazoles with antibacterial activity, among which compounds 16a−e exhibited good antibacterial activity against MRSA after the primary screening (Figure 17). The SARs revealed that benzothiazole compounds whose substituents had strong electronegative groups at the C-2 or C-4 positions and electron-withdrawing groups (EWGs) at the C-3 or C-5 positions of benzene all had strong anti-MRSA activity.…”

Section: -Aminobenzothiazolesmentioning

confidence: 99%

Current Development of Thiazole-Containing Compounds as Potential Antibacterials against Methicillin-Resistant Staphylococcus aureus

Liu,

Xu,

Xue

et al. 2024

ACS Infect. Dis.

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The emergence of multi-drug-resistant bacteria is threatening to human health and life around the world. In particular, methicillin-resistant Staphylococcus aureus (MRSA) causes fatal injuries to human beings and serious economic losses to animal husbandry due to its easy transmission and difficult treatment. Currently, the development of novel, highly effective, and low-toxicity antimicrobials is important to combat MRSA infections. Thiazole-containing compounds with good biological activity are widely used in clinical practice, and appropriate structural modifications make it possible to develop new antimicrobials. Here, we review thiazole-containing compounds and their antibacterial effects against MRSA reported in the past two decades and discuss their structure−activity relationships as well as the corresponding antimicrobial mechanisms. Some thiazole-containing compounds exhibit potent antibacterial efficacy in vitro and in vivo after appropriate structural modifications and could be used as antibacterial candidates. This Review provides insights into the development of thiazole-containing compounds as antimicrobials to combat MRSA infections.

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Section: -Aminobenzothiazolesmentioning

confidence: 99%

Current Development of Thiazole-Containing Compounds as Potential Antibacterials against Methicillin-Resistant Staphylococcus aureus

Liu,

Xu,

Xue

et al. 2024

ACS Infect. Dis.

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Novel Benzothiazole–Benzonitrile‐Based Fluorescent Chromophore: Synthesis, DFT, Antimicrobial Properties

Nami,

Hossan

2024

Luminescence

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The synthetic strategy for the benzothiazole–benzonitrile chromophore 6 involved three sequences of reactions. It was initiated by condensation of 2‐amino‐4‐nitrothiophenol (2) with 4‐(piperidin‐1‐yl)benzaldehyde (1) to produce the corresponding 5‐nitrobenzothiazole compound 3 followed by reduction of compound 3 into the 5‐aminobenzothiazole compound 4 and then ended by condensation of 5‐aminobenzothiazole compound 4 with 4‐formylbenzonitrile (5). The chromophore's absorption and emission spectra have been measured in EtOH and presented good Stokes' shift ( = 8363 cm−1). The DFT configuration of the frontier molecular orbits in gas and solvated ground state (So) were compared with the solvated excited state (S1). The synthesized chromophore 6 was assessed for its antimicrobic properties against a group of bacterial and fungal strains. The minimum inhibitory concentration (MIC) values were determined using standard broth microdilution assay. Notably, chromophore 6 exhibited remarkable MIC values against Staphylococcus aureus and Escherichia coli (< 48 and < 118 μg/mL). Regarding the antibacterial effectiveness against both S. aureus and E. coli, molecular docking was performed to simulate their binding interactions with two protein structures, PDB:2eg7 and PDB:3u2k. The SwissADME study has been applied to explore the pharmacokinetic and pharmacodynamic characteristics of chromophore 6.

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Ligand-based design and synthesis of N'-Benzylidene-3,4-dimethoxybenzohydrazide derivatives as potential antimicrobial agents; evaluation by in vitro, in vivo, and in silico approaches with SAR studies

Eldin

Saleh

Alotaibi

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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Herein, a series of N' -benzylidene-3,4-dimethoxybenzohydrazide derivatives were designed and synthesised to target the multidrug efflux pump (MATE). The antibacterial activities were screened against S. aureus , Acinetobacter , S. typhi , E. coli , and P. aeruginosa , whereas their antifungal activities were screened against C. albicans . Compounds 4a , 4h , and 4i showed the most promising antibacterial and antifungal activities. Moreover, compounds 4h and 4i being the broader and superior members regarding their antimicrobial effects were selected to be further evaluated via in vivo testing using biochemical analysis and liver/kidney histological examination. Additionally, molecular docking was carried out to attain further deep insights into the synthesised compounds' binding modes. Also, ADMET studies were performed to investigate the physicochemical/pharmacokinetics features and toxicity parameters of the synthesised derivatives. Finally, a structure-antimicrobial activity relationship study was established to facilitate further structural modifications in the future. Highlights A series of new N' -benzylidene-3,4-dimethoxybenzohydrazide derivatives were designed and synthesised targeting the multidrug efflux pump (MATE) guided by the pharmacophoric features of the co-crystallized native inhibitor of the target protein. The newly synthesised compounds were assessed through in vitro , in vivo , and in silico approaches. Using the agar well diffusion assay, the antibacterial activities of the synthesised compounds were screened against S. aureus , Acinetobacter , S. typhi , E. coli , and P. aeruginosa , whereas, their antifungal activities were screened against C. albicans . The minimal inhibitory concentration (MIC) and the minimal bactericidal concentration (MBC) of the synthesised compounds were investigated on variable microbial species. Compounds ( 4h and 4i ) -as the broader and superior members regarding their antimicrobial effects- were further evaluated via in vivo testing using bio-chemical analysis and liver/kidney histological examination. A molecular docking study and ADMET in silico ...

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Design, Synthesis, Antibacterial Evaluation and Molecular Docking Studies of Some Newer Baenzothiazole Containing Aryl and Alkaryl Hydrazides

Cited by 5 publications

References 41 publications

Current Development of Thiazole-Containing Compounds as Potential Antibacterials against Methicillin-Resistant Staphylococcus aureus

Current Development of Thiazole-Containing Compounds as Potential Antibacterials against Methicillin-Resistant Staphylococcus aureus

Novel Benzothiazole–Benzonitrile‐Based Fluorescent Chromophore: Synthesis, DFT, Antimicrobial Properties

Ligand-based design and synthesis of N'-Benzylidene-3,4-dimethoxybenzohydrazide derivatives as potential antimicrobial agents; evaluation by in vitro, in vivo, and in silico approaches with SAR studies

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