Synthesis and antibacterial activity of 2-(2,4-dinitrophenyl)-3,5-diphenyl (substituted)-6-aryl-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d] thiazoles

Sahu, Susant Kumar; Mishra, SK; Mohanta, RK; Pattanayak, Shakti Prasad; Panda, CS

doi:10.4103/0250-474x.26686

Cited by 10 publications

(3 citation statements)

References 5 publications

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“…The first step of the general approach involves the conversion of thiazolidinone 1 into its arylidene derivative 2 via Claisen condensation with an aldehyde. In the second step, condensation of 5-arylidenethiazolidinones [16,17] with different hydrazine derivatives was attempted to furnish the desired tetrahydropyrazolo [3,4-d]thiazoles 3 (Scheme 1). Unfortunately, our several attempts by using acidic and basic reagents (acetic acid, sodium acetate, piperidine) and different solvents (methanol, trifluoroethanol, acetonitrile, tetrahydrofuran) did not bring about the desired ring closure reaction.…”

Section: Resultsmentioning

confidence: 99%

Facile synthesis of substituted dihydro-1H-pyrazolo[3,4-d]thiazoles through enaminones of 4-thiazolidinones

Gautam

Chaudhary

2014

Heterocyclic Communications

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A short two-step synthesis of substituted dihydro- 1H-pyrazolo[3,4-d]thiazoles from 4-thiazolidinones is described. 4-Thiazolidinones are easily synthesized by the reaction of thiosemicarbazones of carbonyl compounds and chloroacetic acid. Upon treatment with Lawesson's reagent and dimethylformamide-dimethylacetal, 5-dimethylaminomethylene-3-methylthiazolidine-4-thiones are formed, which undergo condensation with hydrazine derivatives to furnish substituted dihydro-1H-pyrazolo [3,4-d]thiazoles. The structure of the synthesized compounds was established by elemental analysis and analysis of spectral data.

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Section: Resultsmentioning

confidence: 99%

Facile synthesis of substituted dihydro-1H-pyrazolo[3,4-d]thiazoles through enaminones of 4-thiazolidinones

Gautam

Chaudhary

2014

Heterocyclic Communications

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“…The 1, 2,4-triazole exhibit broad spectrum of pharmacological properties such as antibacterial and antifungal activities [20]. The thiazolidin-4one ring has reported to a wide range of pharmacologic activities which include antimicrobial [21], antifungal [22], antitumor [23], anti-diabetic activity [24], anti-inflammatory [25] and stomach toxicity [26]. The first generation antifungal agent triazoles, fluconazole and itraconazole, have revolutionised the treatment of serious fungal infections such as mucosal and invasive candidiasis and cryptococcal meningitis [3].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some new heterocyclic derivatives from aromatic carbonyl compounds and assessment of their antimicrobial activity

2023

JPTCP

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This research work involves synthesis of 18 heterogeneous tetra, penta lateral cyclic compounds (1,3,1,2, Carbothioamide; Thiazole-4-one; Azetidin-2one; Oxazol) compounds. The thiazolidine-4-one was prepared by reaction of p-chlorobenzoic acid with thiosemicarbazide to yield the compound-1, which was treated with p-tolualdehyde to produce compound-2 followed by refluxing (2) with mercaptoacetic acid in dry benzene to yield thiazolidine-4-one compound (3). The reaction of p-nitro benzoic acid with ethanol in the presence of sulphonic acid yielded compound-4 and the reaction of ( 4) with thiosemicarbazide and 4% NaOH led to produce ring closure giving rise to 1,2,4-triazole (6). The thiosemicarbazone was prepared by the reaction of thiosemicarbazide with different aldehyde (7-9) compounds, A2-substituted -1,3-thiazolidine-4-one were synthesized by the reaction of thiosemicarbazone with chloroacetic acid in the presence of anhydrous sodium acetate yielded (10-12) compounds. The compound-15 was made by the reaction of p-amino benzoic acid with ethyl chloroacetate produced compound-13, then treated with urea to obtain the compound-14 followed by 4-phenyl phenacyl bromide to prepare compound-15. The 2azetidinone derivative was synthesized by many steps started from cyclization of p-bromoacetophenon with urea in iodine to yield compound-16 which was reacted with p-bromobenzaldehyde to yield compound-17. Schiff base has been treated with chloroacetyl chloride in the presence of catalytic amount of tri-ethyl amine to produce compound-18. All the synthesized compounds were characterized spectroscopically by both FT-IR spectroscopy and by H1-NMR, and C13-NMR for others. Almost all showed matching features and the validity of the proposed structure. The following synthesized compounds (2,3,6,11,13,15,17,18) were also tested against two types of bacteria (Staphylococcus aureus and Escherichia coli and fungus Candida albicans where they showed potential antibacterial and antifungal activities, respectively.

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“…By heating together 2‐phenyl(substituted)‐3‐aryl‐5‐benzylidine(substituted)‐thiazolidine‐4‐ones and 2,4‐dinitrophenyl hydrazine, Sahu et al synthesized 2‐(2,4‐dinitrophenyl)‐3,5‐diphenyl(substituted)‐6‐aryl‐3,3a,5,6‐tetrahydro‐2H‐pyrazolo[3,4‐d]thiazoles. The synthesized compounds were inspected at a concentration of 100 μg/mL by agar cup plate method to detect the antibacterial activity against St. aureus , Actinomycus pyoginus , E. coli and Klebsiella aeruginosa .…”

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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Synthesis and antibacterial activity of 2-(2,4-dinitrophenyl)-3,5-diphenyl (substituted)-6-aryl-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d] thiazoles

Abstract: thiazoles d] thiazoles d] thiazoles d] thiazoles d] thiazoles

Cited by 10 publications

References 5 publications

Facile synthesis of substituted dihydro-1H-pyrazolo[3,4-d]thiazoles through enaminones of 4-thiazolidinones

Facile synthesis of substituted dihydro-1H-pyrazolo[3,4-d]thiazoles through enaminones of 4-thiazolidinones

Synthesis of some new heterocyclic derivatives from aromatic carbonyl compounds and assessment of their antimicrobial activity

A retrospect on antimicrobial potential of thiazole scaffold

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