Convenient access to 1,3,4-trisubstituted pyrazoles carrying 5-nitrothiophene moiety via 1,3-dipolar cycloaddition of sydnones with acetylenic ketones and their antimicrobial evaluation

Satheesha, N.; Kalluraya, Balakrishna; Lingappa, B. T.; Shenoy, Shaliny; Puranic, Vedavati G.

doi:10.1016/j.ejmech.2007.08.002

Cited by 144 publications

(19 citation statements)

References 4 publications

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“…This representative procedure for preparing an amino acid is identified as Route 1 . 32 Sydnone 2b was then synthesized as an off-white solid (72% overall yield) from the resulting amino acid following Protocol 1 : 1 H NMR (400 MHz, CDCl 3 ) δ 7.74-7.67 (m, 2H), 7.64-7.56 (m, 2H), 6.79 (s, 1H).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes

et al. 2011

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Section: Methodsmentioning

confidence: 99%

Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes

et al. 2011

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“…Especially, thiophene derivatives have been reported to possess broad spectrum of biological properties including anti-inflammatory, analgesic, anti-depressant, anti-microbial and anti-convulsant activities (Molvi et al, 2007;SatheeshaRai et al, 2008;Ashalatha et al, 2007). Now, presently available active anti-epileptic drugs like tiagabine, etizolam, brotizolam are containing thiophene moiety in their structures as active pharmacophore (Polivka et al, 1984;Noguchi et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and vibrational spectral (FT-IR, FT-Raman) studies, NLO properties & NBO analysis of (E)-N'(thiophen-2yl methylene)isonicotinohydrazide using quantum chemical method

Nathiya

Saleem

Bharani

et al. 2018

IJAC

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FT-IR (4000-400 cm-1) and FT-Raman (3500-50 cm-1) spectra of (E)-N'(thiophen-2yl methylene)isonicotinohydrazide (TMINH) molecule was recorded in solid phase. The optimized geometry was calculated by B3LYP method with 6-311++G(d,p) basis set. The harmonic vibrational frequencies, infrared (IR) intensities and Raman scattering activities of the title compound were performed at same level of theory. The complete vibrational assignments were performed on the basis of the Total energy distribution (TED) of the vibrational modes, calculated with scaled quantum mechanical (SQM) method. The calculated first hyperpolarizability may be attractive for further studies on non-linear optical (NLO) properties of material. Stability of the molecule arising from hyperconjugative interaction and charge delocalization was analyzed using natural bond orbital (NBO) analysis. Highest occupied molecular orbital-Lowest unoccupied molecular orbital (HOMO-LUMO) energy gap explains the eventual charge transfer interactions taking place within the title molecule. A study on the electronic properties, such as excitation energies and wavelengths, were performed by time-dependent (TD-DFT) approach. Molecular electrostatic potential (MEP) provides the information on the electrophilic, nucleophilic and free radical prone reactive sites of the molecule. The thermodynamic properties such as heat capacity, entropy and enthalpy of the title compound were calculated at different temperatures in gas phase. 1H and 13C-NMR chemical shifts of the molecule were calculated using Gauge-independent atomic orbital (GIAO) method.To establish information about the interactions between human cytochrome protein and this novel compound theoretically, docking studies were carried out using Schrödinger software.

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“…In recent years, attention has increasingly been given to the synthesis of pyrazole derivatives as a source of new antibacterial agents. Pyrazole derivatives have been reported to possess diverse biological activities such as antibacterial 2,3 , antifungal 4,5 , herbicidal 6 , insecticidal 7 , anti-inflammatory 8,9 , anticonvulsant 10 , antitumor 11 , anti-oxidant 12 , etc. Further, phenoxyethanol has been used as antimicrobial preservative in vaccine preparations 13 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and study of antibacterial activity of some 1-phenyl-3-aryl-5-(4-(2-ethanoloxy) phenyl)-1H-pyrazoles

Goyal¹,

Jain²,

Jain³

2013

Orientjchem.

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A series of 1-phenyl-3-aryl-5-(4-(2-ethanoloxy) phenyl)-1H-pyrazoles were synthesized from chalcones and studied for their in vitro antibacterial activity. Chalcones i.e.,1-aryl-3-(4-hydroxyphenyl) prop-2-en-1-ones, 1 on reaction with phenyl hydrazine yielded the corresponding 1-phenyl-3-aryl-5-(4-hydroxyphenyl)-1H-pyrazoles 2 which on further reaction with 3-chloroethanol furnished the title compounds 3. These compounds were characterized by CHN analyses, IR, mass and 1 H NMR spectral data. All the compounds were evaluated for their in vitro antibacterial activity against two Gram negative strains (Escherichia coli and Pseudomonas aeruginosa) and two Gram positive strains (Bacillus subtilis and Staphylococcus aureus) and their minimum inhibitory concentration (MIC) were determined.

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Convenient access to 1,3,4-trisubstituted pyrazoles carrying 5-nitrothiophene moiety via 1,3-dipolar cycloaddition of sydnones with acetylenic ketones and their antimicrobial evaluation

Cited by 144 publications

References 4 publications

Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes

Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes

Synthesis and vibrational spectral (FT-IR, FT-Raman) studies, NLO properties & NBO analysis of (E)-N'(thiophen-2yl methylene)isonicotinohydrazide using quantum chemical method

Synthesis and study of antibacterial activity of some 1-phenyl-3-aryl-5-(4-(2-ethanoloxy) phenyl)-1H-pyrazoles

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