Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

Aly, Ashraf A.; Hassan, Alaa A.; Makhlouf, Maysa M.; Bräse, Stefan

doi:10.3390/molecules25133036

Cited by 64 publications

(25 citation statements)

References 112 publications

(273 reference statements)

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“…The 3a-d, 4a-d, 5a-d and 6a-d derivatives were prepared according to the method which was described in the relevant literature. [23][24][25][26][27] It is well-known that the thiol-thione tautomeric equilibrium exists in 3a-d, 4a-d and 6a-d compounds.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety

2021

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A number of 1,4-dihydropyridine derivatives (9a-d, 10a-d, and 11a-d) were designed and synthesized by the reaction of 1,3,4-oxadiazole-5-thiones and 1,2,4-triazole-5-thiones to 2,6-dibromomethyl-3,5-diethoxycarbonyl-4-(3-ni-trophenyl)-1,4-dihydropyridine. The synthesized compounds were characterrized using FT-IR, 1H-NMR, 13C-NMR spectral data, ESI-MS, and elemental analysis. The cytotoxicity of the synthesized compounds was evaluated in human breast cancer (MCF-7) cells based on the results of MTT assay. The results indicated that compound Diethyl 4-(3-nitrophenyl)-2,6-bis[((5-(3-nitrophenyl)-1,3,4-oxa-diazol-2-yl)thio)methyl]-1,4-dihydro pyridine-3,5-dicarboxylate (9b) with (IC50 = 23 ? 2.32 ?M) was the most potent derivative against MCF-7 cells. Based on the results, the use of oxadiazole moiety in the C2 and C6 positions of 1,4-di-hydropyridine ring system enhanced the cytotoxic potential of these derivatives. Therefore, some of the oxadiazole-substituted 1,4-DHPs may facilitate further modifications which result in the discovery of potent cytotoxic agents.

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Section: Resultsmentioning

confidence: 99%

“…The CHNS analysis was performed using CHNS-932 Leco analyser. The (3a-d) 23,24 , (4a-d) 25 , (5a-d) 26 and (6a-d) 27 compounds were produced according to the reviewed literature.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety

2021

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“…The experimental conditions for the reaction between benzoic acid and thiosemicarbazide in the presence of PPE with predominant formation of intermediate for the thiadiazole, 2-benzyl hydrazine-1-carbothioamide were found. The new approach has potential for extended application: (1) PPE can be utilized as a mild additive for thiosemicarbazide acylation reaction by carboxylic acids; and (2) the thiosemicarbazide acylation products used for synthesis of thiadiazoles can be also utilized for triazoles synthesis [ 23 ].…”

Section: Discussionmentioning

confidence: 99%

A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives

et al. 2021

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The main purpose of the study was the development of a new method for synthesis of 1,3,4-thiadiazol-2-amine derivatives in a one-pot manner using the reaction between a thiosemicarbazide and carboxylic acid without toxic additives such as POCl3 or SOCl2. The reaction was investigated in the presence of polyphosphate ester (PPE). It was found that, in the presence of PPE, the reaction between the thiosemicarbazide and carboxylic acid proceeds in one-pot through three steps with the formation of corresponding 2-amino-1,3,4-thiadiazole. Using the developed approach five, 2-amino-1,3,4-thiadiazoles were synthesized. The structures of all compounds were proven by mass spectrometry, IR, and NMR spectroscopies.

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“…Fused substituted 1,3,4-thiadiazole was prepared by dehydration of 1-(4-hydroxy-2-phenylthiazol-3(2H)-yl) isothiourea show antitubercular [13]. Due to the presence of bromophenyl group 1,3,4-thiadiazole with show antiviral activity as compound [14,15].…”

Section: Condensation Of Substituted 124-triazole and Isoniazide Givesmentioning

confidence: 99%

Synthesis and Study of Some fused Substituted 1,3,4-Thiadiazoles and 1,2,4-Triazoles from 4-Chloro- phenoxy acetic acid and 2,4-dichlorophenoxy acetic acid

Othman¹

2020

J.Edu.Sci.

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In this work the synthesis of some substituted 1,2,4-triazoles and five ring system's reported. 2-(4-Chlorophenoxy) acetic acid (S1) was synthesis from corresponding substituted phenol by its reaction with chloroacetic acid in sodium hydroxide solution, the acids (Q1 and S1) esterified with methanol and sulfuric acid to give esters (Q2 and S2) which converted to acid hydrazides (Q3 and S3) by their reaction with hydrazine hydrate in ethanol. The acid hydrazides (Q3 and S3) were treated with carbon disulfide in potassium hydroxide solution to give potassium salts (Q4 and S4) the formed salts were treated with hydrazine hydrate to give substituted 4-amino-1,2,4-triazoles (Q5 and S5). 4-Amino-1,2,4-Triazole (Q5 and S5) were converted to (Q6 and S6), (Q9 and S9) and (Q10 and S10) by treating with CS2 in pyridine, urea and chloroacetic acid. While reaction of 4-amino-1,2,4-triazole (Q5 and S5) with phenyl isothiocyanate gave thiosemicarbazide derivatives (Q7 and S7) that converted to N-phenyl substituted 1,2,4triazole (Q8 and S8). The structures of the synthesized compounds were confirmed by physical and spectral data.

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Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

Cited by 64 publications

References 112 publications

Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety

Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety

A Novel Approach to the Synthesis of 1,3,4-Thiadiazole-2-amine Derivatives

Synthesis and Study of Some fused Substituted 1,3,4-Thiadiazoles and 1,2,4-Triazoles from 4-Chloro- phenoxy acetic acid and 2,4-dichlorophenoxy acetic acid

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