Straightforward syntheses of nitriles, acrylates, and acrylamides in aqueous propan-1,2-diol: a catalyst free and waste free methodology

Jayalakshmi, Lakshmi Narayanan; Karuppasamy, Ayyanar; Sivaramakarthikeyan, Ramar; Devadoss, Vellasamy; Ramalingan, Chennan

doi:10.1016/j.tetlet.2015.05.052

Cited by 3 publications

(4 citation statements)

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“…The synthetic strategy pathway of the new pyrazole derivatives is depicted from Schemes – . First, 2-(4-oxothiazolidin-2-ylidene) derivatives ( 1a and 1b ) were used as precursor builders to synthesize many biologically and pharmaceutically active heterocycles. , The thiazolidin-4-one derivatives 1a and 1b were coupled with 1,3-diaryl-1 H -pyrazole-4-carboxaldehyde derivatives 2a and 2b in the presence of ethanol catalyzed with piperidine to produce 4-oxo-5-((substituted-1 H -pyrazol-4-yl)methylene)thiazolidin-2-ylidene derivatives ( 3a , and 3b – d ) and failed to obtain 2-(4-oxo-4,5-dihydrothiazol-2-yl)-3-(1-,3-(diaryl)-1 H -pyrazol-4-yl)acryl derivatives 4a – d . The condensation reaction proceeds through the endocyclic methylene rather than the exocyclic one .…”

Section: Resultsmentioning

confidence: 99%

“…The formation of thiazolin-4-one derivatives 4a–d was supposed to proceed by reaction of 2-((1,3-diaryl-1 H -pyrazol-4-yl)methylene)malononitrile or ethoxy carbonyl malononitrile 6a–d with sulfanylacetic acid in dimethyl formamide (DMF) that contains catalytic amounts of piperidine, but the reaction proceeds by two different pathways. Cyclization of 2-((1,3-diaryl-1 H -pyrazol-4-yl)methylene)malononitrile 6a and 6b formed 3-(1,3-diaryl-1 H -pyrazol-4-yl)-2-(4-oxo-4,5-dihydrothiazol-2-yl)acrylonitrile 4a and 4b , while ethyl 2-cyano-3-(1,3-diaryl-1 H -pyrazol-4-yl)acrylate 6c and 6d formed ethyl 4-amino-2-(1,3-diaryl-1 H -pyrazol-4-yl)thiophene-3-carboxylate 7a and 7b (the suggested mechanism is illustrated in Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…2-(4-Oxothiazolidin-2-ylidene)acetonitrile (1a) and ethyl-2-(4-oxothiazolidin-2-ylidene)acetate (1b) were prepared according to the reported method. 35 Furthermore, 1,3-diphenyl-1H-pyrazole-4-carbaldehyde (2a), 1-phenyl-3-(p-tolyl)-1H-pyrazole-4-carbaldehyde (2b), 37 2-cyano-N- (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide ( 9), 41,56 The MIC of the target compounds (having inhibition zones > 9 mm) was then determined using the broth microdilution method. 58 Two-fold serial dilutions of the tested compounds were prepared to give a concentration range 0.125−128 μg/mL.…”

Section: Discussionmentioning

confidence: 99%

“…2-(4-Oxothiazolidin-2-ylidene)acetonitrile ( 1a ) and ethyl-2-(4-oxothiazolidin-2-ylidene)acetate ( 1b ) were prepared according to the reported method . Furthermore, 1,3-diphenyl-1 H -pyrazole-4-carbaldehyde ( 2a ), 1-phenyl-3-( p -tolyl)-1 H -pyrazole-4-carbaldehyde ( 2b ), 2-cyano- N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)acetamide ( 9 ), , and N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)carbonohydrazonoyldicyanide ( 12 ) were also prepared.…”

Section: Methodsmentioning

confidence: 99%

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In Vitro Antimicrobial Evaluation, Single-Point Resistance Study, and Radiosterilization of Novel Pyrazole Incorporating Thiazol-4-one/Thiophene Derivatives as Dual DNA Gyrase and DHFR Inhibitors against MDR Pathogens

et al. 2022

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A series of thiazol-4-one/thiophene-bearing pyrazole derivatives as pharmacologically attractive cores were initially synthesized using a hybridization approach. All structures were confirmed using spectra analysis techniques (IR, 1 H NMR, and 13 C NMR). In vitro antimicrobial activities, including the minimum inhibitory concentration (MIC), minimum bactericidal/fungicidal concentration (MBC/MFC), and time-kill assay, were evaluated for the most active derivatives 4a, 5a, 7b, 10, and 13. These derivatives were significantly active against the tested pathogens, with compound 7b as the most active derivative (MIC values range from 0.22 to 0.25 μg/mL). In the MBC and MFC, the active target pyrazole derivatives showed -cidal activities toward the pathogenic isolates. Further, the inhibition of biofilm formation of Staphylococcus aureus and Staphylococcus epidermidis was also carried out. Additionally, these derivatives displayed significant antibiofilm potential with a superior % reduction in the biofilm formation compared with Ciprofloxacin. The target derivatives behaved synergistically with Ciprofloxacin and Ketoconazole, reducing their MICs. Hemolytic results revealed that these derivatives were nontoxic with a significantly low hemolytic activity (%lysis range from 3.23 to 15.22%) compared with Triton X-100 and showed noncytotoxicity activity with IC 50 values > 60 μM. In addition, these derivatives proved to be active DNA gyrase and DHFR inhibitors with IC 50 ranging between 12.27−31.64 and 0.52−2.67 μM, respectively. Furthermore, compound 7b showed bactericidal activity at different concentrations in the time-kill assay. Moreover, a gamma radiation dose of 10.0 kGy was efficient for sterilizing compound 7b and enhancing its antimicrobial activity. Finally, molecular docking simulation of the most promising derivatives exhibited good binding energy with different interactions.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

In Vitro Antimicrobial Evaluation, Single-Point Resistance Study, and Radiosterilization of Novel Pyrazole Incorporating Thiazol-4-one/Thiophene Derivatives as Dual DNA Gyrase and DHFR Inhibitors against MDR Pathogens

et al. 2022

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ChemInform Abstract: Straightforward Syntheses of Nitriles, Acrylates, and Acrylamides in Aqueous Propan‐1,2‐diol: A Catalyst Free and Waste Free Methodology.

et al. 2015

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Some New Pyrazolyl Pyrazolones and Cyanopyrazolyl Acrylates: Design, Synthesis and Biological Evaluation

et al. 2019

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The present work is aimed to report several new synthetically and medicinally important pyrazole derivatives. Herein, a series of new 3‐amino‐4‐((3‐aryl‐1‐phenyl‐1H‐pyrazol‐4‐yl) methylene)‐1H‐pyrazol‐5(4H)‐ones (4) were synthesized by the reaction of ethyl 2‐cyano‐3‐(3‐aryl‐1‐phenyl‐1H‐pyrazol‐4‐yl) acrylates (3) and hydrazine hydrate in good yields. All the fourteen compounds (3 and 4) were evaluated for the in vitro antibacterial activity against, Staphylococcus aureus and Bacillus subtilis (Gram Positive), Escherichia coli and Pseudomonas aeruginosa (Gram negative) and the antifungal activity against Candida albicans and Saccharomyces cerevisiae. The tested compounds were found to be active against both the Gram positive strains.

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Straightforward syntheses of nitriles, acrylates, and acrylamides in aqueous propan-1,2-diol: a catalyst free and waste free methodology

Cited by 3 publications

References 44 publications

In Vitro Antimicrobial Evaluation, Single-Point Resistance Study, and Radiosterilization of Novel Pyrazole Incorporating Thiazol-4-one/Thiophene Derivatives as Dual DNA Gyrase and DHFR Inhibitors against MDR Pathogens

In Vitro Antimicrobial Evaluation, Single-Point Resistance Study, and Radiosterilization of Novel Pyrazole Incorporating Thiazol-4-one/Thiophene Derivatives as Dual DNA Gyrase and DHFR Inhibitors against MDR Pathogens

ChemInform Abstract: Straightforward Syntheses of Nitriles, Acrylates, and Acrylamides in Aqueous Propan‐1,2‐diol: A Catalyst Free and Waste Free Methodology.

Some New Pyrazolyl Pyrazolones and Cyanopyrazolyl Acrylates: Design, Synthesis and Biological Evaluation

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