Microwave-Assisted Synthesis of some Novel Azoles and Azolopyrimidines as Antimicrobial Agents

Novel 2-thiazolyl-pyridazinedione derivatives were prepared via multicomponent synthesis under microwave irradiation as ecofriendly energy source and using the eco-friendly naturally occurring chitosan basic catalyst with high/efficient yields and short reaction time. All the prepared compounds were fully characterized by spectroscopic methods, and their in-vitro biological activities were investigated. The obtained results were compared with those of standard antibacterial/antifungal agents. DFT calculations and molecular docking studies were used to investigate the electronic properties and molecular interactions with specific microbial receptors.

show abstract

“…In continuation of our previous work to synthesize bioactive heterocyclic compounds under mild conditions [38][39][40][41][42][43].…”

Section: Synthesismentioning

confidence: 99%

Microwave-Assisted One Pot Three-Component Synthesis of Novel Bioactive Thiazolyl-pyridazinediones As Potential Antimicrobial Agents against Antibiotic-Resistant Bacteria

Abu-Melha

Gomha

Abouzid

et al. 2020

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

“…The preparation of thiazoles was reported in many publications [1][2][3] as they exhibit a significant role in medicinal chemistry [4]. Thiazole derivatives demonstrate good biological spectrum including antibacterial, and antifungal activities [5][6][7][8], in addition to their inhibitory activities of bacterial DNA gyrase B [9].…”

Section: Introductionmentioning

confidence: 99%

Pyridine‐2(1H)‐thiones: Versatile precursors for one‐pot synthesis of new nicotinonitrile‐thiazole hybrids

Sanad

Mekky

Said

et al. 2021

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

In the current study, we report a facile procedure for the preparation of a new series of nicotinonitrile-thiazoles, in excellent isolated yields. For this purpose, pyridine-2(1H)-thiones were investigated as key building blocks for the synthesis of new nicotinonitrile-linked 2-hydroxybenzaldehyde derivatives. To prepare the target thiazole hybrids, a facile one-pot procedure was developed involving amine-mediated reaction of the prior aldehydes, thiosemicarbazide, and the appropriate of hydrazonyl chlorides. The reaction conditions of this one-pot protocol were optimized by repeating the reaction using different solvents and amines. The optimized conditions were conducting the reaction in dioxane containing triethylamine at 100 C for 5 h. The prior protocol gave, in each case, new series of nicotinonitrile-linked thiazole and thiazol-4(5H)-one hybrids, bearing aryldiazenyl or arylhydrazineylidene units. Repeating the prior one-pot protocol using the appropriate halogen containing reagents instead of hydrazonyl chlorides afforded the target thiazoles in excellent isolated yields. By considering their elemental analyses and spectral findings, the structures of the new hybrids were clarified.

show abstract

“…On the contrary, several publications reported the synthesis of 2‐hydrazineylthiazole derivatives [ 7–9 ] because they exhibit an important role in medicinal chemistry, [ 10 ] such as antibacterial and antifungal agents, [ 11–13 ] as well as inhibitors for bacterial DNA gyrase B. [ 14 ] Several thiazoles exhibit promising antibacterial activities by their inhibition of the MurB enzyme, which is responsible for the biosynthesis of bacterial cell walls.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, in‐vitro and in‐silico study of novel thiazoles as potent antibacterial agents and MurB inhibitors

Sanad

Ahmed

Mekky

2020

Archiv der Pharmazie

View full text Add to dashboard Cite

Efficient procedures are herein reported for the synthesis of novel hybrid thiazoles via a one‐pot three‐component protocol. The protocol involves the reaction of novel aldehyde, thiosemicarbazide and halogen‐containing reagents in solvent‐ and catalyst‐free conditions. The structures of the new thiazoles were elucidated by elemental analyses and spectroscopic data. The in‐vitro antibacterial screening and MurB enzyme inhibition assays were performed for the novel thiazoles. The thiazol‐4(5H)‐one derivative 6d, with p‐MeO, exhibits the best antibacterial activities with minimum inhibitory concentration values of 3.9, 3.9, 7.8, and 15.6 μg/ml against Staphylococcus aureus, Klebsiella pneumoniae, Streptococcus mutans, and Escherichia coli, respectively, as compared to the reference antibiotic drugs. It also exhibits the highest inhibition of the MurB enzyme with an IC50 of 8.1 μM. The structure–activity relationship was studied to determine the effect of the structures of the newly prepared molecules on the strength of the antibacterial activities. Molecular docking was also performed to predict the binding modes of the new thiazoles in the active sites of the E. coli MurB enzyme.

show abstract

Microwave-Assisted Synthesis of some Novel Azoles and Azolopyrimidines as Antimicrobial Agents

Cited by 24 publications

References 32 publications

Microwave-Assisted One Pot Three-Component Synthesis of Novel Bioactive Thiazolyl-pyridazinediones As Potential Antimicrobial Agents against Antibiotic-Resistant Bacteria

Microwave-Assisted One Pot Three-Component Synthesis of Novel Bioactive Thiazolyl-pyridazinediones As Potential Antimicrobial Agents against Antibiotic-Resistant Bacteria

Pyridine‐2(1H)‐thiones: Versatile precursors for one‐pot synthesis of new nicotinonitrile‐thiazole hybrids

Synthesis, in‐vitro and in‐silico study of novel thiazoles as potent antibacterial agents and MurB inhibitors

Contact Info

Product

Resources

About