Synthesis of <i>N</i>‐substituted α‐aminoacids from 4‐hydroxycoumarin

Hamdi, Maâmar; Sakellariou, R.; Speziale, V.

doi:10.1002/jhet.5570290723

Cited by 22 publications

(10 citation statements)

References 6 publications

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“…The quick reaction led to the desired product without obtaining any product from the intramolecular condensation of 4-hydroxycoumarin [27]. We have observed previously [28] that the reaction between hydroxyacetylcoumarin and boron compounds substantially increases the acidity of Ha atoms.…”

Section: Resultsmentioning

confidence: 86%

Expedious synthesis for α, β-unsaturated coumarin derivatives using boran chelates: A novel class of potential antibacterial and antioxidant agents

Hamdi

Bouabdallah

Romerosa

et al. 2010

Comptes Rendus. Chimie

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Section: Resultsmentioning

confidence: 86%

Expedious synthesis for α, β-unsaturated coumarin derivatives using boran chelates: A novel class of potential antibacterial and antioxidant agents

Hamdi

Bouabdallah

Romerosa

et al. 2010

Comptes Rendus. Chimie

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“…35-13.42 and between d 8.44-9.10 and d 8.75-9.90 ascribed to =C-NH and (=CH-N) protons, respectively. The splitting was due to the existence of Z and E isomers (Hamdi et al, 1992;Skaellariou et al, 1990). 13 C NMR of reference compounds is also reported.…”

Section: H Nmr Spectramentioning

confidence: 99%

Synthesis, characterization, and urease inhibition of 5-substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-diones

et al. 2010

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5-Substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione and its anilines, amino pyridines and hydrazides derivatives were prepared in a good to excellent yields. In the first step 8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-dione (1) was prepared by reacting 4-methyl-2-aminopyridine, with diethylmalonate. Compounds substituted pyrido[1,2-a]pyrimidine-2,4(3H)-diones (PPMDO) (2)-(17) were prepared by condensing 8-methyl-2H-pyrido[1,2-a] pyrimidine-2,4(3H)-dione in the presence of triethylorthoformte (TEF) and dimethylformamide (DMF), with respective amino components viz. 2-aminoacetophenone, 3-aminoacetophenone, 4-aminoacetophenone, 2,4,6-trimethylaniline, 2-fluoroaniline, 3-fluoroaniline, 4-fluoroaniline, 2-aminothiophenol, 2-amino-4-methylpyridine, 2-amino-5-methylpyridine, 2-amino-5-nitropyridine, Benzoic hydrazide, 4-nitrobenzoic hydrazide, 4-bromobenzoic hydrazide, 4-chlorobenzoic hydrazide and 4-hydroxybenzoic hydrazide, respectively. The chemical structures of all the compounds were elucidated by IR, 1 H-NMR, 13 C-NMR and elemental analysis data. The synthesized compounds were screened for their in vitro urease inhibition activity, by the phenol hypochlorite method. These compounds were found to exhibit either no or low to moderate or significant activity. The compounds (9) and (14) showed comparatively much higher activity. However, the compound (9) was found to be the most active one.

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“…In the NOESY spectrum, EXSY correlations (equilibrium spots) of NH and H-1″ confirmed the presence of two isomers as an inseparable mixture ( Figure S9, Supporting Information ). An extensive literature survey has indicated that 4-hydroxy-6-methyl-2-pyrone and glycine in 2-propanol in the presence of triethyl orthoformate led to 6 ( Scheme 2 ), and the 1 H NMR spectra in previous studies displayed a pair of signals due to the existence of E and Z isomers [ 24 , 25 ]. Comparison of the NMR data of 1 and 6 indicated that they had the same phenomenon of imine–enamine tautomerism ( Figure S10, Supporting Information ).…”

Section: Resultsmentioning

confidence: 99%

Anti-Neuroinflammatory Agent, Restricticin B, from the Marine-Derived Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells

Choi

et al. 2020

Marine Drugs

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A new compound containing a triene, a tetrahydropyran ring and glycine ester functionalities, restricticin B (1), together with four known compounds (2–5) were obtained from the EtOAc extract of the marine-derived fungus Penicillium janthinellum. The planar structure of 1 was determined by detailed analyses of MS, 1D and 2D NMR data. The relative and absolute configurations of 1 were established via the analyses of NOESY spectroscopy data, the comparison of optical rotation values with those of reported restricticin derivatives and electronic circular dichroism (ECD). All the compounds were screened for their anti-neuroinflammatory effects in lipopolysaccharide (LPS)-induced BV-2 microglia cells. Restricticin B (1) and N-acetyl restricticin (2) exhibited anti-neuroinflammatory effects by suppressing the production of pro-inflammatory mediators in activated microglial cells.

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Synthesis of N‐substituted α‐aminoacids from 4‐hydroxycoumarin

Abstract: A new series, the N‐(methylene‐4‐oxocoumarinyl)aminoacids were synthesized by condensation of 4‐hydroxycoumarin with α‐aminoacids in the presence of excess ethyl orthoformate.

Cited by 22 publications

References 6 publications

Expedious synthesis for α, β-unsaturated coumarin derivatives using boran chelates: A novel class of potential antibacterial and antioxidant agents

Expedious synthesis for α, β-unsaturated coumarin derivatives using boran chelates: A novel class of potential antibacterial and antioxidant agents

Synthesis, characterization, and urease inhibition of 5-substituted-8-methyl-2H-pyrido[1,2-a]pyrimidine-2,4(3H)-diones

Anti-Neuroinflammatory Agent, Restricticin B, from the Marine-Derived Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells

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