Enantioseparation and anti-rhinovirus activity of 3-benzylchroman-4-ones

Quaglia, M.G.; Desideri, N.; Bossù, E.; Sgro, Rosanna; Conti, Cinzia

doi:10.1002/(sici)1520-636x(1999)11:5/6<495::aid-chir23>3.0.co;2-5

Cited by 26 publications

(4 citation statements)

References 16 publications

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“…In addition, the synthesized flavonoids exhibited a wide spectrum of anti-picornavirus activity. However, the resolved isomers showed a similar antiviral activity (Quaglia et al, 1999), different to that of the enantiomers of flavans and isoflavans (Quaglia et al, 1991(Quaglia et al, , 1992(Quaglia et al, , 1993. Among homo-isoflavonoids, the most active compounds had a chiral centre in position 3 of the chroman-4-one ring (Desideri et al, 1997).…”

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Synthesis and Anti-Rhinovirus Activity of 2-Styrylchromones

Desideri¹,

Conti

Mastromarino

et al. 2000

Antivir Chem Chemother

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2-Styrylchromones were synthesized as vinylogues of 2-phenylchromones (flavones), a broad class of anti-rhinovirus compounds. The antiviral activity of 2-styrylchromones and 3-hydroxy-1-(2-hydroxyphenyl)-5-phenyl-2,4-pentadien-1-ones, which are intermediates in the synthesis, was evaluated against two selected serotypes of human rhinovirus, 1B and 14, by a plaque reduction assay in HeLa cell cultures. All of the compounds interfered with HRV 1B replication, with the exception of 3-hydroxy-1-(2-hydroxyphenyl)-5-(4-methoxyphenyl)-2,4-pentadien-1-one. The majority of derivatives were also found to be effective against serotype 14, often with a higher potency.

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confidence: 95%

“…Among homo-isoflavonoids, the most active compounds had a chiral centre in position 3 of the chroman-4-one ring (Desideri et al, 1997). However, the resolved isomers showed a similar antiviral activity (Quaglia et al, 1999), different to that of the enantiomers of flavans and isoflavans (Quaglia et al, 1991(Quaglia et al, , 1992(Quaglia et al, , 1993.…”

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Synthesis and Anti-Rhinovirus Activity of 2-Styrylchromones

Desideri¹,

Conti

Mastromarino

et al. 2000

Antivir Chem Chemother

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“…There is very little information available on the analysis of the other two herbal drugs, namely, dragons's blood and Sappan Lignum, except for a method employing Raman spectroscopic analysis [27], which has been found useful to assess the quality of dragon's blood and to distinguish between the resins derived from Dracaena and Croton. Separation of racemic and synthetic homoisoflavones using a chiral phase column has been reported [84].…”

Section: Separation and Analysis Of Homoisoflavonoidsmentioning

confidence: 99%

Naturally Occurring Homoisoflavonoids: Phytochemistry, Biological Activities and Synthesis

Abegaz

Mutanyatta-Comar

Nindi

2007

Natural Product Communications

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This review covers the phytochemical, biological properties, and synthesis of naturally occurring homoisoflavonoids. Homoisoflavonoids are a very important class of secondary metabolites whose numbers have grown from 20 in 1981 to 157 at the present time. They are found to occur in seven plant families. For the purpose of this review they are classified into five groups: 3-benzylchroman-4-ones, 3-benzylflavans, Δ3,9 and Δ2,3 3-benzylchroman-4-ones, benzocyclobutenes (scillascillins) and rearranged homoisoflavonoids (brazilin and related compounds). Biosynthetically, the 3-benzylchroman-4-ones and the 3-hydroxy-derivatives have been shown to arise from a chalcone precursor (sappanchalcone) and there is strong evidence that this isolable intermediate can be converted into the diverse structures such as the benzocyclobutenes (scillascillins) and the rearranged, brazilin-type compounds. Homoisoflavonoids possess a wide range of biological activities, including, antimicrobial, antimutagenic, anti-inflammatory, antidiabetic, etc, properties. The review also surveys the chemical synthesis of natural homoisoflavonoids. Analytical methods for the determination of these important metabolites are also reviewed. The last section is devoted to a brief review of the diagnostic NMR spectroscopic features of homoisoflavonoids. A comprehensive Table has also been compiled listing all known metabolites, their sources, melting points and optical rotation values (where available) and references.

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“…Based on the MTDL drug design strategy, Sterling et al incorporated the pharmacophores of rivastigmine (an AChE inhibitor, Figure 1) and rasagiline (an MAO inhibitor, Figure 2) to a single molecular entity to give a novel dual AChE and MAO-B inhibitors, ladostigil (Figure 2), the Phase II clinical trials of which is in progress 31 . Homoisoflavonoids, which have been found to possess various biological properties, such as antifungal 32 , antiviral 33,34 , anti-proliferative 32 , antioxidant 35 and anti-inflammatory 36 activities, were also proven to be potent and selective MAO-B inhibitors 37 . Inspired by the outcomes of ladostigil, we have developed a series of tacrine-contained hybrids targeted to both AChE and MAO-B in earlier studies 38,39 .…”

Section: Introductionmentioning

confidence: 99%