Synthesis of robustin and related 4-hydroxy-3-phenyl coumarins and isoflavones

Jain, A. C.; Jain, Sanjay Kumar; Singh, Jagjeet

doi:10.1016/s0040-4020(01)97120-0

Cited by 10 publications

(6 citation statements)

References 3 publications

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“…Considering these factors and the close similarity of its spectral properties with those of glabridin, structure 9 was considered most likely for hispaglabridin A. This was confirmed by reaction of glabridin with 3-methyl-but-2-en-l-ol in the presence of BF3-Et20 (22). Four products were seen on tic.…”

Section: Discussionmentioning

confidence: 77%

Antimicrobial Agents From Higher Plants. Antimicrobial Isoflavanoids and Related Substances From Glycyrrhiza glabra L. var. typica

Mitscher¹,

Park²,

Clark³

et al. 1980

J. Nat. Prod.

136

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Bioassay-directed fractionation of Glycyrrhiza glabra L. var. typica resulted in the isolation and characterization of glabridin (I), glabrol (2), glabrene (3), 3-hydroxyglabrol (4), 4'-O-methylglabridin (5), 3'-methoxyglabridin (6), formononetin (7), phaseollinisoflavan (8), hispaglabridin A (9), hispaglabridin B (13), salicylic acid and O-acetyl salicylic acid. Of these, hispaglabridin A, hispaglabridin B, 4'-O-methylglabridin, glabridin, glabrol and 3-hydroxyglabrol possess significant antimicrobial activity in vitro; hispaglabridin A, hispaglabridin B, 3'-methoxyglabridin, 4'-O-methylglabridin 3-hydroxyglabrol, phaseollinisoflavan, salicylic acid, and O, acetyl salicylic acid are newly found in Glycyrrhiza sp.; and hispaglabridin A, hispaglabridin B, 3'-methoxyglabridin, 4'-O-methylglabridin, and 3-hydroxyglabrol are new to the literature and their structures are proposed herein.

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Section: Discussionmentioning

confidence: 77%

Antimicrobial Agents From Higher Plants. Antimicrobial Isoflavanoids and Related Substances From Glycyrrhiza glabra L. var. typica

Mitscher¹,

Park²,

Clark³

et al. 1980

J. Nat. Prod.

136

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“…In robustin 44 synthesis the addition of 2‐methyl‐3‐buten‐2‐ol to 2,4‐dihydroxy‐6‐methoxy phenylbenzylketone 139 using boron trifluoride diethyl etherate in dioxane at room temperature proceeded to give the mixture of the mono‐substituted products, prenylated at C‐3 and C‐5 for 140 and 141 , respectively, as well as the disubstituted product 142 (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

The Synthetic and Biological Aspects of Prenylation as the Versatile Tool for Estrogenic Activity Modulation

2017

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Prenyl group is a ubiquitous structural moiety in natural compounds showing a wide spectrum of different biological activities with potential benefits for human health. This review presents the current knowledge on the prenylation of aromatic compounds such as flavonoids and coumarins. The references to the ‘classical’ methods that encompass Friedel‐Crafts reaction using prenyl alcohol and boron trifluoride, and alkylation with prenyl bromide in the presence of strong bases are given in comparison with the most state‐of‐the‐art prenylation methods. This review highlights the marked advance that has been achieved so far and makes prenyl group installment a versatile tool in the synthesis of drug candidates, natural compounds, and building blocks. Different aspects of prenyl group assembling methods are reported in more than 30 syntheses of natural substances and their analogues. The last part highlights a role of prenylation in flavonoid bioavailability and bioactivity modulation especially regarding their estrogenicity.

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“…Coumarins with benzodioxol and benzodioxane structural fragments are often isolated from plants [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. The natural bioregulators of coumarin series are convenient subjects for chemical modifications.…”

Section: Introductionmentioning

confidence: 99%