ChemInform Abstract: An Efficient, Simple, One Pot Synthesis of Dihydropyrimidine‐2(1H)‐ones Using Phosphorus Pentoxid.

Deshmukh, M. B.; Anbhule, Prashant V.; Jadhav, S. D.; Mali, A. R.; Jagtap, S. S.; Deshmukh, S. A.

doi:10.1002/chin.200802148

Cited by 6 publications

(3 citation statements)

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“…The one-proton singlet at δ 5.47 is due to C-4 proton of the dihydropyrimidinone ring. Of the three downfield oneproton singlets, the broad singlet at δ 8.74 is assigned to N 1 H of the DHPM, while the one at δ 9.17 is attributed to NH of amide and the broad far downfield singlet at δ 10.0 is due to N 3 H. These assignments are in good agreement with published data [8,15] and further supported by its 13 C NMR data.…”

Section: Spectral Analysis Of Synthesized Compoundssupporting

confidence: 89%

Synthesis, antibacterial studies, and molecular modeling studies of 3,4-dihydropyrimidinone compounds

Ramachandran

Arumugasamy²,

Edayadulla

et al. 2015

J Chem Biol

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The syntheses of dihydropyrimidinones (DHPMs) using solvent-free grindstone chemistry method. All the synthesized compounds exhibited significant activity against pathogenic bacteria. The current effort has been developed to obtain new DHPM derivatives that focus on the bacterial ribosomal A site RNA as a drug target. Molecular docking simulation analysis was applied to confirm the target specificity of DHPMs. The crystal structure of bacterial 16S rRNA and human 40S rRNA was taken as receptors for docking. Finally, the docking score, binding site interaction analysis revealed that DHPMs exhibit more specificity towards 16S rRNA than known antibiotic amikacin. Accordingly, targeting the bacterial ribosomal A site RNA with potential drug leads promises to overcome the bacterial drug resistance. Even though, anti-neoplastic activities of DHPMs were also predicted through prediction of activity spectra for substances (PASS) tool. Further, the results establish that the DHPMs can serve as perfect leads against bacterial drug resistance.

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Section: Spectral Analysis Of Synthesized Compoundssupporting

confidence: 89%

Synthesis, antibacterial studies, and molecular modeling studies of 3,4-dihydropyrimidinone compounds

Ramachandran

Arumugasamy²,

Edayadulla

et al. 2015

J Chem Biol

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“…Anthracene supplied by Aldrich with 99 % purity was used as received. The 5-ethoxy-carbonyl-4-cinnamyl-6-methyl-3,4-dihydropyrimidine-2(1H)-one was synthesized in accordance with the method reported in literature [14] and was purified by recrystallization from ethanol. This was identified by IR, proton NMR spectral data and m.p.…”

Section: Experimental Materialsmentioning

confidence: 99%

Synthesis and photophysical studies on 5-ethoxycarbonyl-4-cinnamyl-6-methyl- 3,4-dihydropyrimidine-2(1H)-one in various solvents

Lad¹,

Mote²,

Bhattar³

et al. 2009

Bull. Chem. Soc. Eth.

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The 5-ethoxycarbonyl-4-cinnamyl-6-methyl-3,4-dihydropyrimidine-2(1H)-one (DHPM) was synthesized via Biginelli reaction and was characterized by NMR, IR, UV-Visible absorption and fluorescence spectroscopy. The fluorescence of the compound exhibits red shift from its absorption spectra and correlated with the solvent polarity. The quantum yield of fluorescence of the DHPM was found to vary with solvent polarity. The absorption spectrum of DHPM overlaps significantly with anthracene fluorescence spectrum. Therefore fluorescence quenching experiments were performed in 1,4-dioxane. The fluorescence of anthracene was found to be quenched and quenching is in accordance with Stern-Volmer relation. The Stern-Volmer constant (KSV = 2.52 x 10 3 M-1) was obtained. The quenching rate constant (kq = 7.145 x 10 11 M-1 s-1) was calculated from the fluorescence lifetime of anthracene measured on time resolved fluorimeter (TRF) in absence of DHPM. The fluorescence quenching explained on the basis of energy transfer from anthracene to DHPM derivative. The rate constant as well as efficiency of energy transfer depends on the distance between donor and acceptor and found to be r = 6.39 nm which indicates energy transfer.

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“…3,4-dihydropyrimidin-2(1H)-ones, Biginelli compounds, have been synthesized by condensing aldehyde, ethylacetoacetate and urea or thiourea under acidic conditions [10]. Methanesulfonic acid [11] and phosphorus pentoxide [12] have been used as catalysts in the past decade. Both of these transformations require conventional heating and use of organic solvents.…”

Section: Introductionmentioning

confidence: 99%

A Green, Expeditious, One-Pot Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones Using a Mixture of Phosphorus Pentoxide-Methanesulfonic Acid at Ambient Temperature

Borse

Patil

et al. 2012

ISRN Organic Chemistry

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ChemInform Abstract: An Efficient, Simple, One Pot Synthesis of Dihydropyrimidine‐2(1H)‐ones Using Phosphorus Pentoxid.

Abstract: Phosphorus Pentoxid. -(DESHMUKH*, M. B.; ANBHULE, P. V.; JADHAV, S. D.; MALI, A. R.; JAGTAP, S. S.; DESHMUKH, S. A.; Indian J. Chem., Sect. B: Org.

Cited by 6 publications

References 0 publications

Synthesis, antibacterial studies, and molecular modeling studies of 3,4-dihydropyrimidinone compounds

Synthesis, antibacterial studies, and molecular modeling studies of 3,4-dihydropyrimidinone compounds

Synthesis and photophysical studies on 5-ethoxycarbonyl-4-cinnamyl-6-methyl- 3,4-dihydropyrimidine-2(1H)-one in various solvents

A Green, Expeditious, One-Pot Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones Using a Mixture of Phosphorus Pentoxide-Methanesulfonic Acid at Ambient Temperature

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