Synthesis and Anticonvulsant Activity (Chemo Shock) of N-1(substituted-N-4[(4-Oxo-3-Phenyl-3, 4-Dihydro-Quinazoline-2-Ylmethyl) Semicarbazones

Yadav, Meena; Tripathi, Laxmi; Goswami, Diptendu

doi:10.22159/ajpcr.2017.v10i4.16876

Cited by 4 publications

(3 citation statements)

References 42 publications

(43 reference statements)

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“…Although semicarbazones are of considerable interest due to a broad spectrum of their biomedical applications, structural data for these species are quite scarce and desultory. Our processing of the Cambridge Structural Database (CSD; the Supporting Information; Figure S2) revealed only 8 relevant XRD structures .…”

Section: Resultsmentioning

confidence: 99%

“…This functionalization has never been reported as metal‐free or metal‐catalyzed protocols. Our interest in the synthesis of semicarbazones was additionally motivated by the available evidence that they can act as urease inhibitor,, used as insecticides, and demonstrate antifungal, anticonvulsant, antimicrobial, antiproliferative and antitumor activities.…”

Section: Introductionmentioning

confidence: 99%

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Gold‐Catalyzed Functionalization of Semicarbazides with Terminal Alkynes to Achieve Substituted Semicarbazones

et al. 2019

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Gold‐catalyzed functionalization of semicarbazides (ArNHCONHNH2) with various terminal alkynes R2C≡CH (R2 = Alk or Ar) in the presence of Ph3PAuNTf2 (3 mol‐%) grants a range of substituted semicarbazones (16 examples; 64–93 %). This novel metal‐catalyzed coupling proceeds under mild conditions (PhCl, 60 °C) and demonstrates a high functional group tolerance; the reaction is sensitive to the electronic effects of the substituents in terminal alkynes. Inspection of XRD solid‐state structures of three obtained semicarbazones proved their dimerization via weak to moderate strength hydrogen bonding. The structures of the semicarbazones in solutions were studied by concentration dependent 1H NMR and 2D NMR and these experiments proved the presence of H‐bonds between two molecules. The nature and energy of H‐bonding (3.8–5.1 kcal/mol), degree of electron density delocalization, and rotational barriers via various bonds in the equilibrium model structures were studied by DFT calculations at the M06‐2X/6‐311++G** level of theory.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Gold‐Catalyzed Functionalization of Semicarbazides with Terminal Alkynes to Achieve Substituted Semicarbazones

et al. 2019

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“…The compounds screened for their antimicrobial potential against S. pyogenes, S. aureus, P. aeruginosa, and E. coli. All the derivatives have shown promising antimicrobial activity, but the compounds with isopropyl and indole derivatives were having more promising and reproducible effect [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

The SYNTHESIS, SCREENING OF NOVEL 1-SUBSTITUTED-3-(4-OXO-2-PHENYLQUINAZOLIN-3(4H)-YL) UREA AND THIOUREA ANALOGUES AS POTENT ANTIBACTERIALS

Dhokale

Snehal

Bansode

et al. 2019

Int J Pharm Pharm Sci

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Objective: The proposed study is an attempt to determine antibacterial activity of synthesized novel 1-substituted-3-(4-oxo-2-phenylquinazolin-3(4H)-yl) urea and thiourea analogues as potent antibacterials against S. aureus and E. coli bacteria. Methods: The present study reports new series of 1-substituted-3-(4-oxo-2-phenylquinazolin-3(4H)-yl) urea and thiourea derivatives as potent antibacterial agents. Reagents used in the present study were of synthetic grade and solvents were used after distillation. Novel quinazolinone analogues were synthesized by considering substitution pattern, characterization of the synthesized analogues was performed using various techniques like Thin layer chromatography, Melting point, Infrared spectroscopy, Proton NMR spectrometry and Mass spectrometry. TLC of the synthesized analogues was carried out by using (toluene: methanol in the ratio 2:1), melting point was found by open capillary method, IR spectrum was recorded on JASCO V-530, 1H NMR was recorded on Bruker Avance Spectrometer and Mass spectra were obtained from G6460A, triple quadrupole/MS/MS system. In vitro antibacterial activity was performed against S. aureus and E. coli. Results: Six derivatives of quinazolinone analogues were synthesized. The structures of 1-substituted-3-(4-oxo-2-phenylquinazolin-3(4H)-yl) urea and thiourea derivatives were confirmed by physical and spectral analysis. Synthesized molecules showed Rf of 0.45-0.80 in toluene: methanol mobile phase, melting point was carried out by open capillary method and were in range of 90-210 ° C, IR spectrum was recorded in range of 14000-400 cm-1and showed characteristic peaks of NH and of C-O-NH, 1H NMR of the compounds was distinct to confirm structures with delta values in the range of 7.53-11.960, Mass spectra proved parent peaks of synthesized compounds confirming molecular weight. The compounds were assayed for antibacterial activity against S. aureus and E. coli using ciprofloxacin as standard. The synthesized analogues have shown good yield and comparable antibacterial. Conclusion: The present study delivers a convenient and efficient protocol for the quinazolinone analogues synthesis.

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Synthesis, molecular docking and DFT studies on biologically active 1,4-disubstituted-1,2,3-triazole-semicarbazone hybrid molecules

et al. 2019

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Synthesis and Anticonvulsant Activity (Chemo Shock) of N-1(substituted-N-4[(4-Oxo-3-Phenyl-3, 4-Dihydro-Quinazoline-2-Ylmethyl) Semicarbazones

Cited by 4 publications

References 42 publications

Gold‐Catalyzed Functionalization of Semicarbazides with Terminal Alkynes to Achieve Substituted Semicarbazones

Gold‐Catalyzed Functionalization of Semicarbazides with Terminal Alkynes to Achieve Substituted Semicarbazones

The SYNTHESIS, SCREENING OF NOVEL 1-SUBSTITUTED-3-(4-OXO-2-PHENYLQUINAZOLIN-3(4H)-YL) UREA AND THIOUREA ANALOGUES AS POTENT ANTIBACTERIALS

Synthesis, molecular docking and DFT studies on biologically active 1,4-disubstituted-1,2,3-triazole-semicarbazone hybrid molecules

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