Synthesis of New Pyrazolothiazole Derivatives from 4-Thiazolidinones

Turgut, Zühal; Yolaçan, Çiğdem; Aydoğan, Feray; Bağdatlı, Emine; Öcal, Nüket

doi:10.3390/12092151

Cited by 35 publications

(16 citation statements)

References 8 publications

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“…literature, [48][49][50] however, no detailed design and study of biological properties specially on nematicidal activity was made. This fact aroused our interest to design and synthesize some of the interesting and new bis-pyrazolothiazoles from bissalicylaldehyde and to evaluate their nematicidal activity along with antimicrobial activities.…”

Section: Synthesis Nematicidal and Antimicrobial Properties Of Bis-[mentioning

confidence: 99%

Synthesis, Nematicidal and Antimicrobial Properties of Bis-[4-methoxy-3-[3-(4-fluorophenyl)-6-(4-methylphenyl)-2(aryl)-tetrahydro-2H-pyrazolo[3,4-d]thiazol-5-yl]phenyl]methanes

Reddy

Srinivas

Nagaraj

2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new series of bis-[4-methoxy-3-[3-(4-fluorophenyl)-6-(4-methylphenyl)-2-(aryl)-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d][1,3]thiazol-5-yl]phenyl]methanes 6a-r was synthesized by the reaction of arylidine derivative of methylene-bis-thiazolidinones 5a-c with aryl/alkyl hydrazines. Chemical structures of all the new compounds were established by IR, (1)H-NMR, (13)C-NMR, MS and elemental data. The compounds 6a-r were evaluated for their nematicidal activity against Ditylenchus myceliophagus and Caenorhabdites elegans by aqueous in vitro screening technique. Amongst them compounds containing N-benzylpyrazole moiety (6d, 6j, 6p), and N-methylpyrazole moiety (6f, 6l, 6r) showed significant nematicidal activity against both the test nematodes with LD(50) 160-210 ppm, almost equal to the oxamyl standard. Further, these compounds 6a-r were screened for their antibacterial (MZI, MIC and MBC) activity against three representative Gram-positive bacteria viz. Bacillus subtilis (MTCC 441), Bacillus sphaericus (MTCC 11), Staphylococcus aureus (MTCC 96) and three Gram-negative bacteria viz. Pseudomonas aeruginosa (MTCC 741), Klebsiella aerogenes (MTCC 39), Chromobacterium violaceum (MTCC 2656) and also screened for their antifungal (MZI, MIC and MFC) activity against four fungal organisms viz. Candida albicans (ATCC 10231), Aspergillus fumigatus (HIC 6094), Trichophyton rubrum (IFO 9185) and Trichophyton mentagrophytes (IFO 40996). Most of these new compounds showed appreciable activity against test bacteria and fungi, and emerged as potential molecules for further development.

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Section: Synthesis Nematicidal and Antimicrobial Properties Of Bis-[mentioning

confidence: 99%

Synthesis, Nematicidal and Antimicrobial Properties of Bis-[4-methoxy-3-[3-(4-fluorophenyl)-6-(4-methylphenyl)-2(aryl)-tetrahydro-2H-pyrazolo[3,4-d]thiazol-5-yl]phenyl]methanes

Reddy

Srinivas

Nagaraj

2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Furthermore, the 4‐thiazolidinone ring system is a core structure in medicinal chemistry, owing to its broad spectrum of biological activities such as anticancer, antitubercular, anti‐inflammatory, antibacterial, antimycobacterial, anti‐HIV, anticonvulsant, antiprotozoan, antihistaminic, and as analgesic agents …”

Section: Introductionmentioning

confidence: 99%

Synthesis and in vitro evaluation of novel tetralin‐pyrazolo[3,4‐b]pyridine hybrids as potential anticancer agents

Hamza

Hamdy

Zarie

et al. 2019

Journal of Heterocyclic Chem

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“…Besides, they are also utilised as chemical antecedents for many compounds, for example polymethine cyanine dyes (El-Aal 2003). More recently, these derivatives were used in the synthesis of pyrazolothiazole derivatives (Turgut et al 2007) and monofluoro-β lactams (Fuchigami et al 1992). Consequently, number of protocols have been developed and reported for the synthesis of 4-thiazolidinone including one-step, two-step or via one-pot multicomponent reactions (Kumar et al 2013).…”

Section: Introductionmentioning

confidence: 99%

Utilisation of Home Laundry Effluent (HLE) as a catalyst for expeditious one-pot aqueous phase synthesis of highly functionalised 4-thiazolidinones

et al. 2013

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BackgroundThe impact of global warming and associated climate changes have built up pressure to focus on the option of green chemistry over traditional one for long term sustainability of the environment. Considering the fact, for the first time, efficient HLE catalysed expeditious one-pot synthesis of highly functionalised 4-thiazolidinones has been developed.ResultsThese hybrid molecules were synthesized in good to excellent yields. The ease of work-up of the reactions less time required and mild conditions are notable features of this protocol. It was inferred that halogen containing derivatives were well suited to this condensation-cyclization reaction with varying rates to afford 4-thiazolidine derivatives. In general, the substitution on the aldehyde part was shown as a main determinant for reaction time and the product yield.ConclusionFor the first time home laundry effluent (HLE) owing to the surfactant like property has been successfully utilised as catalyst for the synthesis of a series of novel 4-thiazolidinone derivatives through one pot, three component condensation-cyclization reaction. The uniqueness of the present protocol lies in the operational simplicity, ability to reduce the demand for organic solvents, reduce the energy and carbon footprint, and meet a wide range of economic needs.Electronic supplementary materialThe online version of this article (doi:10.1186/2193-1801-2-466) contains supplementary material, which is available to authorized users.

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Synthesis of New Pyrazolothiazole Derivatives from 4-Thiazolidinones

Abstract: Abstract:The synthesis of new 2,3,5,6-aryl substituted tetrahydro-2H-pyrazolo[3,4-d]-thiazoles 4a-j as potential biologically active compounds by the cyclocondensation of phenyl hydrazine with new 5-arylidene derivatives 2a-j of 2,3-disubstituted-1,3-thiazolidin-4-ones 1a-e is reported.

Cited by 35 publications

References 8 publications

Synthesis, Nematicidal and Antimicrobial Properties of Bis-[4-methoxy-3-[3-(4-fluorophenyl)-6-(4-methylphenyl)-2(aryl)-tetrahydro-2<i>H</i>-pyrazolo[3,4-<i>d</i>]thiazol-5-yl]phenyl]methanes

Synthesis, Nematicidal and Antimicrobial Properties of Bis-[4-methoxy-3-[3-(4-fluorophenyl)-6-(4-methylphenyl)-2(aryl)-tetrahydro-2<i>H</i>-pyrazolo[3,4-<i>d</i>]thiazol-5-yl]phenyl]methanes

Synthesis and in vitro evaluation of novel tetralin‐pyrazolo[3,4‐b]pyridine hybrids as potential anticancer agents

Utilisation of Home Laundry Effluent (HLE) as a catalyst for expeditious one-pot aqueous phase synthesis of highly functionalised 4-thiazolidinones

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