Synthesis, Antibacterial Activity and Quantum-Chemical Studies of Novel 2-Arylidenehydrazinyl-4-arylthiazole Analogues

Alam, Mohammad Sayed; Liu, Lijun; Lee, Yong‐Eok; Lee, Dong‐Ung

doi:10.1248/cpb.59.568

Cited by 46 publications

(17 citation statements)

References 23 publications

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“…In our series, 4-Br-phenyl derivative displayed the most powerful growth inhibitory effect against C. albicans strain. Para-substitution of phenyl ring was endowed with better antimicrobial properties, this aspect being in agreement with literature [31,32]. These results indicate that introduction of different electron-withdrawing atoms or groups in different positions of the aryl ring [33] plays an important role in the antimicrobial activity of the hydrazones tested here.…”

Section: -18supporting

confidence: 91%

New Hydrazones Bearing Thiazole Scaffold: Synthesis, Characterization, Antimicrobial, and Antioxidant Investigation

et al. 2015

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New series of hydrazones 5-18 were synthesized, in good yields, by reacting 4-methyl-2-(4-(trifluoromethyl)phenyl)thiazole-5-carbohydrazide with differently substituted benzaldehyde. The resulting compounds were characterized via elemental analysis, physico-chemical and spectral data. An antimicrobial screening was done, using Gram (+), Gram (−) bacteria and one fungal strain. Tested molecules displayed moderate-to-good growth inhibition activity. 2,2-Diphenyl-1-picrylhydrazide assay was used to test the antioxidant properties of the compounds. Monohydroxy (14-16), para-fluorine (13) and 2,4-dichlorine (17) derivatives exhibited better free-radical scavenging ability than the other investigated molecules.

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Section: -18supporting

confidence: 91%

New Hydrazones Bearing Thiazole Scaffold: Synthesis, Characterization, Antimicrobial, and Antioxidant Investigation

et al. 2015

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“…20) Briefly, to a stirred solution of thiosemicarbazide (1 mmol) in an ethanolwater mixture, an ethanolic solution of a substituted benzaldehyde (1 mmol) was added slowly and refluxed for 10-20 min. After cooling the reaction mixture to ambient temperature, the mixture was filtered to provide a solid crude product, which was crystallized from ethanol to furnish pure compounds 2a-j at yields of 83-94%.…”

Section: Methodsmentioning

confidence: 99%

“…2-(3,4-Dihydroxybenzylidine)hydrazinecarbothioamide (2a) (20), 136 (65). The spectral data of compounds 2g-j was described in our previous study.…”

Section: Methodsmentioning

confidence: 99%

“…The spectral data of compounds 2g-j was described in our previous study. 20) General Procedure for the Preparation of 1,3-Thiazole Analogues (3a-p) The novel 1,3-thiazole analogues were prepared by the modification of our previous methods.…”

Section: Methodsmentioning

confidence: 99%

“…16) More recently, Netalkar et al 17) reported that some novel transition metal complexes of benzothiazoles showed DNA binding and cleavage properties and anti-tuberculosis activity, and TuranZitouni et al 18) reported some new (3,4-diaryl-3H-thiazol-2-ylidene) pyrimidin-2-yl amine derivatives had anti-HIV activity and selective human MAO-B inhibitory activity of novel 1-(4-arylthiazol-2-yl)-2-(3-methylcyclohexylidene) hydrazine derivatives. 19) In our previous study, 20) we observed that 2-arylidenehydrazinyl-4-arylthiazoles possessing bromine and methoxy group at the 4-position of benzylidine phenyl ring showed significant antibacterial activity. Therefore, in the present study, we designed and synthesized a series of novel 2-arylidenehydrazinyl-4-arylthiazole analogues bearing different substituents, e.g.…”

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confidence: 93%

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Synthesis, Antibacterial, Antioxidant Activity and QSAR Studies of Novel 2-Arylidenehydrazinyl-4-arylthiazole Analogues

2014

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A novel series of 2-arylidenehydrazinyl-4-arylthiazole analogues (3a-p) was designed and synthesized in excellent yields using a rapid, simple, efficient methodology. Sixteen novel compounds were screened for in vitro antimicrobial activities against eleven bacteria, namely, Staphylococcus aureus, Listeria monocytogenes, Enterococcus faecalis, Bacillus subtilis, Klebsiella pneumonia, Citrobacter freundii, Cronobacter sakazakii, Salmonella enteritidis, Escherichia coli, Yersinia pestis, and Pseudomonas aeruginosa. All 16 compounds showed significant anti-bacterial activities against both Gram-positive and Gram-negative bacteria. In particular, compound 3g showed potent inhibition of E. coli and K. pneumonia, compound 3i inhibited E. faecalis, compound 3n S. tythi and E. faecalis, and compound 3c E. coli and C. sakazakii. In fact, our results indicate that most of the compounds synthesized exhibit strong antibacterial activity. The qualitative structureantibacterial activity relationships (QSAR) were studied using the physicochemical and quantum-chemical parameters of the ab initio Hartree-Fock model at the RHF/6-31G level of theory. A good qualitative correlation between predicted physicochemical parameters (log P and polar surface area (PSA)) and antibacterial activity has been found. The synthesized compounds were also evaluated for antioxidant activity. Compounds 3j, 3a and 3i exhibited the greatest antioxidant activity, with IC 50 values of 0.66, 0.81, and 1.08 µM, respectively, which were comparable to that of ascorbic acid (IC 50 0.87 µM). The promising antibacterial and antioxidant activities of some of these synthesized 2-arylidenehydrazinyl-4-arylthiazole derivatives, together with the results of quantum-chemical studies, could be helpful for the development of drugs to combat diseases caused by microorganisms and oxidative stress.

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Selective Formation of 2‐(2‐Aminophenyl)benzothiazoles via Copper‐Catalyzed Aerobic C−C Bond Cleavage of Isatins

Wang

Deng

et al. 2020

Adv Synth Catal

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Herein, two kinds of structurally significant 2-(2-aminophenyl)benzothiazoles were selectively generated by the copper-catalyzed aerobic CÀ C bond cleavage of isatins. Morpholine served not only as a reactant but a promoter in the threecomponent assembly of 2-(2-aminophenyl)benzothiazoles. Also it proved to be an efficient additive for the formation of free amino 2-(2-aminophenyl) benzothiazoles. This protocol represents a stepeconomic entry to the title compounds with a range of compatible functionalities.

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Synthesis, Antibacterial Activity and Quantum-Chemical Studies of Novel 2-Arylidenehydrazinyl-4-arylthiazole Analogues

Cited by 46 publications

References 23 publications

New Hydrazones Bearing Thiazole Scaffold: Synthesis, Characterization, Antimicrobial, and Antioxidant Investigation

New Hydrazones Bearing Thiazole Scaffold: Synthesis, Characterization, Antimicrobial, and Antioxidant Investigation

Synthesis, Antibacterial, Antioxidant Activity and QSAR Studies of Novel 2-Arylidenehydrazinyl-4-arylthiazole Analogues

Selective Formation of 2‐(2‐Aminophenyl)benzothiazoles via Copper‐Catalyzed Aerobic C−C Bond Cleavage of Isatins

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