Ipriflavone, an Antiostheophorotic Agent

Böcskei, Zsolt; Simon, Kálmán; Varga, Márton; Hermecz, István

doi:10.1107/s0108270195015241

Cited by 4 publications

(3 citation statements)

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“…The somewhat lower values for II, by virtue of the possibility of a longer side chain may show a less flapping tendency(higher potential barrier to free rotation) than I. These dihedral angles are nevertheless, in the range observed in the previously determined isoflavone structures from 32° to 75° (LAKSHMI, KUMAR, SENTHILSELVAN & SUBRAMANIAN, 1996;SHOJA , 1992 a,b;BRETON, PRECIGOUX, COURSEILLE & HOSPITAL, 1975;KANEDA, IITAKA & SHIBATA, 1973;ACHARYA, PURANIK, TAVALE & ROW, 1986;BÖCSKEL, SIMON, VARGA & HERMECZ, 1996;MAZUREK et al, 1998). Despite the biochemical activity of flavones and isoflavones few are listed in the Cambridge data file.…”

Section: Resultsmentioning

confidence: 94%

The Crystal Structures of O,O-Dimethylalpinumisoflavone and 5-O-Methyl-4'-O-(3-methyl-but-2-en-1-yl)alpinumisoflavone

Kingsford-Adaboh

Osei-Fosu

Asomaning

et al. 2001

Cryst. Res. Technol.

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The petrol extract of the rootbark of Milletia Thonningii obtained by column chromatography afforded sixteen different crystalline samples to be isolated. The crystal structures of two of these compounds, O,O‐Dimethylalpinumisoflavone (I) and 5‐O‐Methyl‐4'‐O‐(3‐methyl‐but‐2‐en‐1‐yl)alpinumisoflavone (II) are being reported here. (II) has two independent molecules in the asymmetric unit and differs from (I) in a longer side chain attached to C(15) of the phenyl ring. The structural features of the three molecules in the title compounds are reported and compared. The derivatives, being subject of this article are the first reported crystal structures where the isoflavone fragment is fused to a further six membered ring that results in a tricyclic ring system. The benzopyrone fragments are planar. The dihedral angles between the benzopyrone fragment and the phenyl ring being 55.38(6)° for (I) and 44.75(15)° /44.64(15)° for the respective independent molecules of (II) are within the range of values observed for similar structures.

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Section: Resultsmentioning

confidence: 94%

The Crystal Structures of O,O-Dimethylalpinumisoflavone and 5-O-Methyl-4'-O-(3-methyl-but-2-en-1-yl)alpinumisoflavone

Kingsford-Adaboh

Osei-Fosu

Asomaning

et al. 2001

Cryst. Res. Technol.

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“…47 Analysis of the synthetic isoflavone, ipriflavone (7-isopropoxyisoflavone) which is used in the treatment of bone loss in osteoporosis, indicated that the molecular structure was dominated by the dihedral angle of 50 between the planes of the aryl and benzopyran moieties. 48 The synthesis of isoflavones can be broadly divided into three main synthetic pathways: the formylation of deoxybenzoins, the oxidative rearrangement of chalcones and flavanones, and the arylation of a preformed chromanone ring. Synthetic procedures using 2 -hydroxyphenyl benzyl ketones and 2 -hydroxychalcones have been reviewed.…”

Section: Isoflavonesmentioning

confidence: 99%

Isoflavonoids and related compounds

Boland¹,

Donnelly²

1998

Nat. Prod. Rep.

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“…The ten atoms of the fused benzopyran ring system are approximately planar and inclined at 8.7(3)°to the aryl ring. In 6-hydroxyflavone 14 this angle is 9.8(2)°but in ipriflavone 15 it is closer to 50.0°. The torsion angle C2 -C1 -C12 -C17 is 8.9(8)°and the C1 -C12 bond length here is 1.457( 7) Å.…”

Section: X-ray Crystallographymentioning

confidence: 89%