Microwave‐Assisted Synthesis, Antioxidant, and Antimicrobial Evaluation of Piperazine‐Azole‐Fluoroquinolone Based 1,2,4‐Triazole Derivatives

Ozdemir, Serap Basoglu; Demirbaş, Neslihan; Demırbas, Ayhan; Ayaz, Faik Ahmet; Çolak, Nesrin

doi:10.1002/jhet.3336

Cited by 19 publications

(7 citation statements)

References 41 publications

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“…To achieve the goal, as starting materials were used 4-R1-3-(morpholinomethyl)-4H-1,2,4triazole-5-thioles (1-5) which were synthesized and described by us earlier [18]. Synthesis 4-((5-((cyclohexylmethyl)thio)-4-R1-4H-1,2,4-triazol-3-yl)methyl)morpholine (6)(7)(8)(9)(10) was realized due to the interaction of initial thiols 1-5 with (bromomethyl)cyclohexane with adding the equivalent of sodium hydroxide in 1-propanol ( Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

“…The obtained elemental analysis values are in good agreement with theoretical data. Furthermore, the molecular weight and individuality of all compounds(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) were confirmed by GS/MS. In substances chromatograms, there are individual peaks of the synthesized compounds, and the mass spectra of these compounds showed a molecular peak corresponding to the exact theoretical mass.…”

mentioning

confidence: 78%

“…Thus, the synthetic strategy actively examines modern approaches to optimizing the process of creating new molecules [3,4]. One of the options for this optimization is the use of microwave synthesis systems, which allow not only to increase the final output of reaction products but also to significantly accelerate its yield [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

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Microwave-Assisted Synthesis of Some New Derivatives of 4-Substituted-3-(Morpholinomethyl)-4h-1,2,4-Triazole-5-Thioles

Shcherbyna¹

2019

Ankara Universitesi Eczacilik Fakultesi Dergisi

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Objective: The purpose of this work is to synthesize new series of 4-((5-((cyclohexylmethyl)thio)-4-R1-4H-1,2,4-triazol-3-yl)methyl)morpholines and 4-((4-R1-5-(pyridin-2-ylthio)-4H-1,2,4-triazol-3yl)methyl)morpholines using a microwave synthesis system. Material and Method: As starting compounds are used 4-R1-3-(morpholinomethyl)-4H-1,2,4-triazole-5thioles (where, R1=H, methyl, ethyl, phenyl, amino). Synthesis was carried out using a microwave synthesis system Milestone Flexi Wave. The structure of synthesized compounds is confirmed by the use of modern methods of analysis 1 H NMR, 13 C NMR spectroscopy, elemental analysis and gas chromatography-mass spectrometry (GS/MS). Result and Discussion: As a result of the conducted experiment, the synthesis method is optimized for 4-((5-((cyclohexylmethyl)thio)-4-R1-4H-1,2,4-triazol-3-yl)methyl)morpholines and 4-((4-R1-5-(pyridin-2-ylthio)-4H-1,2,4-triazol-3-yl)methyl)morpholines by microwave irradiation. It was established that the reactions proceed to the end in all described conditions, but the reaction with the parameters t=10 min, T=160 о С is the most technologically optimal. This approach has allowed reducing energy costs and increasing the yield of target compounds. As a result, a class of new derivatives of 1,2,4-triazole has been obtained, which can be used in further pharmacological studies as valuable biological agents.

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Section: Resultsmentioning

confidence: 99%

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confidence: 78%

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Microwave-Assisted Synthesis of Some New Derivatives of 4-Substituted-3-(Morpholinomethyl)-4h-1,2,4-Triazole-5-Thioles

Shcherbyna¹

2019

Ankara Universitesi Eczacilik Fakultesi Dergisi

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“…Of these compounds, 1,2,4triazoles are known to be used to improve the pharmacokinetic properties (excretion, metabolism, distribution and absorption) of drugs [8]. Furthermore, 1,2,4-triazole derivatives have significant pharmacological properties [9], for example analgesic [10], antifungal [11], antibacterial [12,13], anticonvulsant [14], anti-inflammatory [15], antiviral [16], antimalarial [17] and antioxidant [18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Identification of Some New Derivatives of ([Benzyl Thio) Benzimidazole -N- (Methylene-5-Yl)] - 4,5- Di Substituted 1,2,4-Triazole and Evaluation of Their Activity as Antimicrobial and Anti-Inflammatory Agents

Suaad

Halah

Yasser

2021

eijs

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New 2-Mercaptobenzimidazole derivatives were synthesized. 4,5-disubsitituted 1,2,4-Triazole compounds 1b-2c were synthesized from 2-(benzylthio) benzimidazole compound a, which was then reacted with (NaH) in dioxane at a temperature of (0-5 C°) to produce the salt of compound a. Then the salt was reacted with ethyl chloro acetate to yield Ethyl 2-(benzylthio) benzimidazole acetate compound b. Compound b was converted to triazole derivatives by two pathways. The first pathway was reacting compound b with semicarbazide, thiosemicarbazide and phenylsemicarbazide in DMSO as a solvent to gain compounds 1b-3b, which were then cyclized by refluxed with 2N (NaOH) to yield 1,2,4-triazole derivatives compounds 4b-6b. The second pathway involved the treatment of compound b with hydrazine hydrate to produce N-acetohydrazide-2-(benzyl thio) benzimidazole c. Compound c was refluxed with carbon disulfide (CS2) in KOH alcoholic solution to obtain the salt compound 1c. The salt was treated with hydrazine hydrate to yield 1,2,4-triazole derivative compound 2c. The newly synthesized compounds b-2c were identified by FTIR, 1H-NMR and 13C-NMR and their physical properties were measured. Furthermore, their anti-microbial activities were tested against two Gram-positive and two Gram-negative bacteria and against one strain of fungi. Also, some of these synthesized compounds were tested for their anti-inflammatory activities.

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“…The search for biologically active compounds among 1,2,4-triazole derivatives is being carried out by teams of scientists from many countries of the world [7][8][9][10][11][12][13][14]. An interesting fact remains the attempt of many scientists to combine 1,2,4-triazole with various functional substitutes, which in the "complex" may be promising for the detection of new types of pharmacological activity.…”

Section: Introductionmentioning

confidence: 99%

Microwave Synthesis of New N-R-3-(Alkylthio)-5-(Thiophen-2-Ylmethyl)-1,2,4-Triazol-4-Amines

Сафонов

2020

Ankara Universitesi Eczacilik Fakultesi Dergisi

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Objective: The aim of this work is to synthesize 3-(alkylthio)-5-(thiophen-2-ylmethyl)-1,2,4-triazol-4amines by the Milestone Flexi Wave microwave synthesis system and to prove structure synthesized compounds.Material and Method: The initial compounds 3-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-5-thioles (1-5) were synthesized at the Department of Toxicological and Inorganic Chemistry of the Zaporizhzhya State Medical University (Ukraine). Milestone Flexi Wave microwave synthesis system was used to synthesize 3-(alkylthio)-5-(thiophen-2-ylmethyl)-1,2,4-triazol-4-amines. The elemental analysis of synthesized compounds was established by the universal analyzer Elementar Vario L cube (CHNS). The 1 H spectra (at 400 MHz and 100 MHz) were recorded in DMSO-d6 on a Varian MR-400 spectrometer and analysed with ADVASP™ Analyzer program. The completeness of the reactions and the individuality of the resulting compounds were controlled by the gas chromatograph Agilent 7890B with a 5977B mass spectrometry detector.Result and Discussion: The reaction was carried out in an alcoholic medium by adding a catalytic amount of HCl to 5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiols. Methyl and i-propyl alcohols were used as alcohols. The mixture was heated for 45 minutes at a temperature of 150°C, a pressure 14.4 bar, ΔMW = 200 W.The signals of are consented with the proposed structure. The elemental analysis (CHNS) was accomplished for synthesized compounds to confirm their basic chemical structures and revealed acceptable agreement with the calculated percentages.

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Microwave‐Assisted Synthesis, Antioxidant, and Antimicrobial Evaluation of Piperazine‐Azole‐Fluoroquinolone Based 1,2,4‐Triazole Derivatives

Cited by 19 publications

References 41 publications

Microwave-Assisted Synthesis of Some New Derivatives of 4-Substituted-3-(Morpholinomethyl)-4h-1,2,4-Triazole-5-Thioles

Microwave-Assisted Synthesis of Some New Derivatives of 4-Substituted-3-(Morpholinomethyl)-4h-1,2,4-Triazole-5-Thioles

Synthesis and Identification of Some New Derivatives of ([Benzyl Thio) Benzimidazole -N- (Methylene-5-Yl)] - 4,5- Di Substituted 1,2,4-Triazole and Evaluation of Their Activity as Antimicrobial and Anti-Inflammatory Agents

Microwave Synthesis of New N-R-3-(Alkylthio)-5-(Thiophen-2-Ylmethyl)-1,2,4-Triazol-4-Amines

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