6-Methoxy-2-(2,3,4-trimethoxyphenyl)-4H-1-benzopyran-4-one (6,2',3',4'-tetramethoxyflavone)

Wallet, Jc.; Gaydou, E. M.; Tinant, Bernard; Declercq, Jean‐Paul; Baldy, A.; Bonifassi, Pierre

doi:10.1107/s0108270190000257

Cited by 6 publications

(3 citation statements)

References 2 publications

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“…These naturally occurring polyphenolics exhibit a wide range of biological properties (Brahmachari andGorai 2006, 2007), including antioxidant, antitumour, cytotoxic, enzyme inhibitory, antimicrobial, insecticidal and oestrogenic activities; they are also used in the treatment of diabetes and cancer (Wallet et al 1990). Flavonoids are also major components of many plant drugs (e.g.…”

Section: Introductionmentioning

confidence: 99%

X-ray study of weak interactions in two flavonoids

et al. 2007

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X-ray diffraction studies were carried out on single crystals of two flavonoids, viz. 5-hydroxy-6,7,4′-trimethoxyflavone, C 18 H 16 O 6 , (I) and 5-hydroxy-3,7,4′-trimethoxyflavone, C 18 H 16 O 6 , (II). Crystal structures of both the flavonoids were solved by direct methods and refined by full-matrix least-squares procedures. In both the molecules, the benzopyran moiety is planar. The dihedral angle between the phenyl ring and the benzopyran portion is 5⋅50(4)° in (I) and 29⋅11(5)° in (II). In (I), the crystal packing is influenced by O-H…O hydrogen bonds, and weak C-H…O and π…π interactions whereas in (II) the crystal structure is stabilized by the presence of four intermolecular short contacts of the type C-H…O. There is also one C-H…π hydrogen bond with H… centroid distance of < 2⋅7 Å. The molecules are further stabilized by π-π interactions.

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Section: Introductionmentioning

confidence: 99%

X-ray study of weak interactions in two flavonoids

et al. 2007

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“…The present work employs the AM1 semiempirical method in order to calculate some molecular properties (descriptors) of 45 flavonoid compounds (reported in the literature as potent and selective antipicornavirus agents 4 ) and 9 new ones − that are used in an activity prediction study. Our objective in this work is to investigate, in a qualitative way, the structure−activity relationship (SAR) of flavone compounds by using quantum chemical descriptors and other molecular properties.…”

Section: Introductionmentioning

confidence: 99%

“…Structure-activity relationship (SAR) studies with biological molecules can aid in the developing of more effective compounds (by using molecular properties that can be responsible for the biological activity) with the goal of understanding the interaction mechanism between drugs and their biological receptors. [5][6][7][8] The present work employs the AM1 semiempirical method 9 in order to calculate some molecular properties (descriptors) of 45 flavonoid compounds (reported in the literature as potent and selective antipicornavirus agents 4 ) and 9 new ones [10][11][12] that are used in an activity prediction study. Our objective in this work is to investigate, in a qualitative way, the structure-activity relationship (SAR) of flavone compounds by using quantum chemical descriptors and other molecular properties.…”

Section: Introductionmentioning

confidence: 99%

A Study on the Antipicornavirus Activity of Flavonoid Compounds (Flavones) by Using Quantum Chemical and Chemometric Methods

Souza

Molfetta

Honório

et al. 2004

J. Chem. Inf. Comput. Sci.

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The AM1 semiempirical method is employed to calculate a set of molecular properties (variables) of 45 flavone compounds with antipicornavirus activity, and 9 new flavone molecules are used for an activity prediction study. Principal Component Analysis (PCA), Hierarchical Cluster Analysis (HCA), Stepwise Discriminant Analysis (SDA), and K-Nearest Neighbor (KNN) are employed in order to reduce dimensionality and investigate which subset of variables should be more effective for classifying the flavone compounds according to their degree of antipicornavirus activity. The PCA, HCA, SDA, and KNN methods showed that the variables MR (molar refractivity), B(9) (bond order between C(9) and C(10) atoms), and B(25) (bond order between C(11) and R(7) atoms) are important properties for the separation between active and inactive flavone compounds, and this fact reveals that electronic and steric effects are relevant when one is trying to understand the interaction between flavone compounds with antipicornavirus activity and the biological receptor. In the activity prediction study, using the PCA, HCA, SDA, and KNN methodologies, three of the 9 new flavone compounds studied were classified as potentially active against picornaviruses.

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¹³C NMR spectra of a series of 2′,3′,4′‐trimethoxyflavones. Reinvestigation of signal assignment in ¹³C NMR spectra of flavones

Wallet¹,

Gaydou²

1993

Magnetic Reson in Chemistry

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6-Methoxy-2-(2,3,4-trimethoxyphenyl)-4H-1-benzopyran-4-one (6,2',3',4'-tetramethoxyflavone)

Cited by 6 publications

References 2 publications

X-ray study of weak interactions in two flavonoids

X-ray study of weak interactions in two flavonoids

A Study on the Antipicornavirus Activity of Flavonoid Compounds (Flavones) by Using Quantum Chemical and Chemometric Methods

¹³C NMR spectra of a series of 2′,3′,4′‐trimethoxyflavones. Reinvestigation of signal assignment in ¹³C NMR spectra of flavones

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6-Methoxy-2-(2,3,4-trimethoxyphenyl)-4H-1-benzopyran-4-one (6,2',3',4'-tetramethoxyflavone)

Cited by 6 publications

References 2 publications

X-ray study of weak interactions in two flavonoids

X-ray study of weak interactions in two flavonoids

A Study on the Antipicornavirus Activity of Flavonoid Compounds (Flavones) by Using Quantum Chemical and Chemometric Methods

13C NMR spectra of a series of 2′,3′,4′‐trimethoxyflavones. Reinvestigation of signal assignment in 13C NMR spectra of flavones

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¹³C NMR spectra of a series of 2′,3′,4′‐trimethoxyflavones. Reinvestigation of signal assignment in ¹³C NMR spectra of flavones