Synthesis of Angular Pyrrolocoumarins

Gonzalez, Jose; Lobo‐Antunes, Joana; Pérez‐Lourido, Paulo; Santana, Lourdes; Uriarte, Eugenio

doi:10.1055/s-2002-20952

Cited by 22 publications

(9 citation statements)

References 13 publications

(14 reference statements)

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“…The dihedral angles between these planes in crystal packing are AˆA=2.65(3)°, AˆB = 13.39(3)°, BˆC = 2.99(4)° and AˆC =10.76(2)°. The bond lengths and bond angles observed in this structure are comparable with those reported for other coumarin derivatives in CSD (e.g., GEHWEW [33] and MOFJIA [34]). The packing of molecules in the unit cell gives some indication of the types of interaction that such a molecule would show in biological systems.…”

Section: Resultssupporting

confidence: 84%

Determination of the Absolute Configuration of Aegelinol by Crystallization of Its Inclusion Complex with β-Cyclodextrin

et al. 2012

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Abstract:The absolute configuration and structure of aegelinol, a pyranocoumarin isolated from Ferulago asparagifolia Boiss (Apiaceae), has been determined by crystallography. Crystal structure of the inclusion complex of aegelinol in β-cyclodextrin was determined (a = 15.404(1) Å, b = 15.281(1) Å, c = 17.890(1) Å, α = 99.662(1), β = 113.4230(1), γ = 102.481(1)°, P1; R 1 = 6.71%) and allowed unambiguous determination of the absolute configuration of the stereogenic center of aegelinol. The pyranocoumarin guest is included within the cylindrical cavity formed by dimeric β-cyclodextrin molecules with a head-to-head arrangement. Crystal structure of aegelinol alone was also determined (a = 6.8921(3) Å, b = 11.4302(9) Å, c = 44.964(3) Å, P2 1 2 1 2 1 ; R 1 = 4.44%) and allowed precise determination of its geometry. Aegelinol crystallizes with three molecules in the asymmetric unit held together by H-bonds and π-stacking interactions. OPEN ACCESSCrystals 2012, 2 1442

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Section: Resultssupporting

confidence: 84%

Determination of the Absolute Configuration of Aegelinol by Crystallization of Its Inclusion Complex with β-Cyclodextrin

et al. 2012

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“…59 The most comprehensive approach was recently revealed by Yao and coworkers, 60 who reported several strategies towards both pyrrolo[f]/[g]coumarins. 59 The most comprehensive approach was recently revealed by Yao and coworkers, 60 who reported several strategies towards both pyrrolo[f]/[g]coumarins.…”

Section: Scheme 28 Synthesis Of Angelicinmentioning

confidence: 99%

π-Expanded coumarins: synthesis, optical properties and applications

et al. 2015

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Coumarins fused with other aromatic units have recently emerged as a hot topic of research. Their synthesis is partly based on classical methodologies such as Pechmann reaction or Knoevenagel condensation, but it also sparked the discovery of completely new pathways. In very recent years so-called vertically-expanded coumarins were synthesized, effectively expanding the portfolio of existing architectures. A subtle relationship exists between the structure of fused coumarins and their optical properties. Although absorption of UV-radiation and light is unifying theme among these π-expanded coumarins, the fluorescence properties strongly depend on the structure. The mode of fusion, the type of additional ring and the presence of electron-donating and electron-withdrawing substituents all influence the photophysical parameters. Recent advances made it possible to modulate their absorption from 300 nm to 550 nm, resulting in new coumarins emitting orange light. This review serves as a guide through both synthesis strategies and structure-property relationship nuances. Strong intramolecular charge-transfer character made it possible to reach suitable values of two-photon absorption crosssection. Photophysical advantages of π-expanded coumarins have been already utilized in fluorescence probes and two-photon excited fluorescence microscopy.

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“…In the first the formation of the pyrrole fragment is achieved from the reaction of aminocoumarins and benzoin, [8] or the Fischer reaction of the corresponding hydrazones, [9 -12] or from amine oxide rearrangement of the corresponding N-methyl-N-prop-2-ynylcoumarins, [13] or from chloroacetylation of aminocoumarin and subsequent reduction [14]. In the second route the pyranone fragment is introduced by Pechmann cyclization of hydroxyindole [15] or by formylation of hydroxyindole and cyclization with acetic anhydride.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel angular fused Pyrrolocoumarins

Kontogiorgis

Litinas

Makri

et al. 2008

Journal of Enzyme Inhibition and Medicinal Chemistry

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Angular pyrrolocoumarins were synthesized from the reaction of 4-hydroxyindole or 5-hydroxyindole with DMAD and PPh 3 and were tested for anti-inflammatory and antioxidant activity. These compounds significantly inhibited the carrageenininduced paw edema (60.5% -73.4%) and have important scavenging activity. Although their interaction with the free stable radical DPPH is not high, compound 9 is the most potent (73.4%) in the in vivo experiment. Compound 7 seems to be a potent LOX inhibitor. An attempt was made to correlate the biological results with their structural characteristics and physicochemical parameters.

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Synthesis of Angular Pyrrolocoumarins

Cited by 22 publications

References 13 publications

Determination of the Absolute Configuration of Aegelinol by Crystallization of Its Inclusion Complex with β-Cyclodextrin

Determination of the Absolute Configuration of Aegelinol by Crystallization of Its Inclusion Complex with β-Cyclodextrin

π-Expanded coumarins: synthesis, optical properties and applications

Synthesis and biological evaluation of novel angular fused Pyrrolocoumarins

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