Oxidative rearrangement of 2′-hydroxychalcones having no substituent at the 3′- and 5′-positions with thallium(<scp>III</scp>) nitrate in methanol

Hòrie, Tokunaru; Kawamura, Yasuhiko; Sakai, Chikako; Akita, Ayako; Sasagawa, Masahiro; Yamada, Toshihide

doi:10.1039/p19960001987

Search citation statements

Order By: Relevance

Paper Sections

Select...

Synthesis Of Isoflavones By Thallium(iii) Nitrate1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2004

2011

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

(1 citation statement)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A mechanism has also been suggested for this transformation (Scheme 12). Later, this oxidative transformation of the 2'hydroxychalcones 16 for the synthesis of variously substituted aurones 17 was successfully utilized by other laboratories [158][159][160][161].…”

Section: Synthesis Of Isoflavones By Thallium(iii) Nitratementioning

confidence: 99%

Synthesis of isoflavones

Lévai

2004

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Section: Synthesis Of Isoflavones By Thallium(iii) Nitratementioning

confidence: 99%

Synthesis of isoflavones

Lévai

2004

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Biomimetic Syntheses and Antiproliferative Activities of Racemic, Natural (−), and Unnnatural (+) Glyceollin I

et al. 2011

View full text Add to dashboard Cite

A 14-step biomimetic synthetic route to glyceollin I (1.5% overall yield) was developed and deployed to produce the natural enantiomeric form in soy, its unnatural stereoisomer, and a racemic mixture. Enantiomeric excess was assessed by asymmetric NMR shift reagents and chiral HPLC. Antiproliferative effects were measured in human breast, ovarian, and prostate cancer cell lines, with all three chiral forms exhibiting growth inhibition (GI) in the low to mid μM range for all cells. The natural enantiomer, and in some cases the racemate, gave significantly greater GI than the unnatural stereoisomer for estrogen receptor positive (ER(+)) versus ER(-) breast/ovarian cell lines as well as for androgen receptor positive (AR(+)) versus AR(-) prostate cancer cells. Surprisingly, differences between ER(+) and ER(-) cell lines were not altered by media estrogen conditions. These results suggest the antiproliferative mechanism of glyceollin I stereoisomers may be more complicated than strictly ER interactions.

show abstract

Oxidative rearrangement of 2′-hydroxychalcones having no substituent at the 3′- and 5′-positions with thallium(III) nitrate in methanol

Cited by 2 publications

References 9 publications

Synthesis of isoflavones

Synthesis of isoflavones

Biomimetic Syntheses and Antiproliferative Activities of Racemic, Natural (−), and Unnnatural (+) Glyceollin I

Contact Info

Product

Resources

About