Saturated heterocycles, part 161 [1]. Synthesis of 2‐hydroxycycloalkyl‐substituted 1,3,4‐oxadiazoles, 1,3,4‐thiadiazoles and 1,2,4‐triazoles

Fülöp, Ferenc; Semega, E.; Dombi, György; Bernáth, G.

doi:10.1002/jhet.5570270424

Cited by 21 publications

(2 citation statements)

References 16 publications

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“…1 . The previous methods for the synthesis of 2-acylamino-1,3,4-oxadiazoles: ( a ) Two-step procedure to synthesize 2-acylamino-1,3,4-oxadiazoles by cyclization and amidization [22,23,24,25,26,27,28,29,30,31,32,33,34,35]; ( b ) One-step procedure to synthesize 2-acylamino-1,3,4-oxadiazoles by desulfurated cyclization [11,36,37,38,39,40,41]. 2 .…”

Section: Figure Schemes and Tablesmentioning

confidence: 99%

“…To date, different methods have been developed for the synthesis of these heterocyles. The most straightforward synthesis relies on the cyclization of corresponding thiosemicarbazide derivatives with several desulfurating agents [22], such as 1,3-dibromo-5,5-dimethylhydantoin [23]; p -tosyl chloride [24,25]; alkylating agents [26,27], such as methyl iodide and ethyl bromoacetate; carbodiimides [28,29]; mercury (II) acetate [30,31,32]; oxone [33]; and POCl 3 [34] (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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A Useful Synthesis of 2-Acylamino-1,3,4-oxadiazoles from Acylthiosemicarbazides Using Potassium Iodate and the Discovery of New Antibacterial Compounds

Wen

et al. 2019

Molecules

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A useful method for the synthesis of 2-acylamino-1,3,4-oxadiazoles was developed. By using potassium iodate as an oxidant in water at 60 °C, a wide range of 2-acylamino-1,3,4-oxadiazoles were afforded in moderate to excellent yields within two hours. This method could provide a facile shortcut to generate a series of 2-acylamino-1,3,4-oxadiazoles in medicinal chemistry. Interestingly, some highly potent antibiotic compounds were found through this synthetic method, and some of them displayed a significant improvement in activity compared with the corresponding 1,4-diacylthiosemicarbazides. Compound 2n was the most active against Staphylococcus aureus with MIC (minimum inhibitory concentration) of 1.56 mg/mL, and compounds 2m and 2q were the most active against Bacillus subtilis with MIC of 0.78 mg/mL. The preliminary cytotoxic activities of the most potent compounds 2m, 2n, and 2q against the androgen-independent (PC-3) prostate cancer cell line were more than 30 μM (IC50 > 30 μM).

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Section: Figure Schemes and Tablesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Useful Synthesis of 2-Acylamino-1,3,4-oxadiazoles from Acylthiosemicarbazides Using Potassium Iodate and the Discovery of New Antibacterial Compounds

Wen

et al. 2019

Molecules

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ChemInform Abstract: Saturated Heterocycles. Part 161. Synthesis of 2‐Hydroxycycloalkyl‐Substituted 1,3,4‐Oxadiazoles (VII), (IX), 1,3,4‐Thiadiazoles (V) and 1,2,4‐Triazoles (IV).

Fueloep¹,

Semega²,

Dombi³

et al. 1990

ChemInform

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Synthesis of some novel pyridine compounds containing bis‐1,2,4‐triazole/thiosemicarbazide moiety and investigation of their antioxidant properties, carbonic anhydrase, and acetylcholinesterase enzymes inhibition profiles

Bulut

Koçyiğit

Geçibesler

et al. 2017

J Biochem & Molecular Tox

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Some novel derivatives of thiosemicarbazide and 1,2,4-triazole-3-thiol were synthesized and evaluated for their biological activities. The title compounds were prepared starting from readily available pyridine-2,5-dicarboxylic acid. The reaction carboxylic acid with absolute ethanol afforded the corresponding dimethyl pyridine-2,5-dicarboxylate (1). The reaction of dimethyl-2,5-pyridinedicarboxylate (1) with hydrazine hydrate good yielded pyridine-2,5-dicarbohydrazide (2). Refluxing compound 2 with alkyl/aryl isothiocyanate derivatives for 3-8 h afforded 1,4-disubstituted thiosemicarbazides (3a-e). Base-catalyzed intra-molecular dehydrative cyclization of these intermediates furnished the 4,5-disubstituted bis-mercaptotriazoles (4a-e) in good yield (85%-95%). Among the target compounds, 2,2 ′ -(pyridine-2,5-diyldicarbonyl)bis[N-(pmethoxyphenyl)hydrazinecarbothioamide] (3c) showed very high activity with value of 72.93% against 1,1-diphenyl-2-picrylhydrazyl free radical at the concentration of 25 g/mL. The inhibitory effects of the target compounds against acetylcholinesterase (AChE), hCA I, and II were studied. AChE, cytosolic hCA I and II isoforms were potently inhibited by synthesized these derivatives with K i s in the range of 3.07 ± 0.76-87.26 ± 29.25 nM against AChE, in the range of 1.47 ± 0.37-10.06 ± 2.96 nM against hCA I, and in the range of 3.55 ± 0.57-7.66 ± 2.06 nM against hCA II, respectively.

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Saturated heterocycles, part 161 [1]. Synthesis of 2‐hydroxycycloalkyl‐substituted 1,3,4‐oxadiazoles, 1,3,4‐thiadiazoles and 1,2,4‐triazoles

Cited by 21 publications

References 16 publications

A Useful Synthesis of 2-Acylamino-1,3,4-oxadiazoles from Acylthiosemicarbazides Using Potassium Iodate and the Discovery of New Antibacterial Compounds

A Useful Synthesis of 2-Acylamino-1,3,4-oxadiazoles from Acylthiosemicarbazides Using Potassium Iodate and the Discovery of New Antibacterial Compounds

ChemInform Abstract: Saturated Heterocycles. Part 161. Synthesis of 2‐Hydroxycycloalkyl‐Substituted 1,3,4‐Oxadiazoles (VII), (IX), 1,3,4‐Thiadiazoles (V) and 1,2,4‐Triazoles (IV).

Synthesis of some novel pyridine compounds containing bis‐1,2,4‐triazole/thiosemicarbazide moiety and investigation of their antioxidant properties, carbonic anhydrase, and acetylcholinesterase enzymes inhibition profiles

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