ChemInform Abstract: Chemistry of 2‐Amino‐3‐cyanopyridines

Gouda, Moustafa A.; Berghot, M. A.; Ghani, Ghada E. Abd El; Khalil, Abd El‐Galil M.

doi:10.1002/chin.201413261

Cited by 4 publications

(6 citation statements)

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“…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]. Numerous thiazole derivatives display promising antibacterial activity via their inhibitory efficacy of the MurB enzyme involved in the biosynthesis of bacterial cell walls [8][9][10][11][12].…”

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

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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.

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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

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“…From 2‐(2‐cyano‐acetylamino)‐4,5,6,7‐tetrahydro‐benzo[b]thiophene‐3‐carboxamide, Gouda et al reported 4,5,6,7‐tetrahydrobenzothiophene moiety based thiazole and pyrazole derivatives. The derivatives were assessed for antimicrobial activity against Bacillus theringiensis , K. pneumoniae , B. fabe and F. oxysporum by agar diffusion technique in comparison to Ampicillin.…”

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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“…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

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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.

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ChemInform Abstract: Chemistry of 2‐Amino‐3‐cyanopyridines

Abstract: Review: 47 refs.

Cited by 4 publications

References 1 publication

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

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

A retrospect on antimicrobial potential of thiazole scaffold

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

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