10383. Dehydroequol

Nomenclature

CAS number: 81267-65-4
3-(4-Hydroxyphenyl)-2H-1-benzopyran-7-ol; 7-hydroxy-3-(4-hydroxyphenyl)-2H-1-benzopyran; isoflav-3-ene-4′,7-diol; haginin E; idronoxil; phenoxodiol; NV-06.
C15H12O3; mol wt 240.25.
C 74.99%, H 5.03%, O 19.98%.

Description and references

Naturally occurring isoflavonoid derivative with pro-apoptotic, antitumor activity; proposed metabolite of daidzein, q.v. Prepn: A. J. Liepa, Aust. J. Chem. 34, 2647 (1981). Isoln from the legume, Lespedeza homoloba Nakai, Leguminosae: T. Miyase et al., Phytochemistry 52, 303 (1999) DOI PubMed. Preparative method from daidzein: A. Heaton, N. Kumar, WO 0049009 (2000 to Novogen). Synthesis: S.-R. Li et al., Tetrahedron Lett. 50, 2121 (2009) DOI. Vasodilatory activity: J. P. F. Chin-Dusting et al., Br. J. Pharmacol. 133, 595 (2001) DOI PubMed. Inhibition of DNA topoisomerase II: A. I. Constantinou, A. Husband, Anticancer Res. 22, 2581 (2002). Mechanism of apoptotic action: A. B. Alvero et al., Cancer 106, 599 (2006) DOI PubMed. Clinical pharmacokinetics: P. L. de Souza et al., Cancer Chemother. Pharmacol. 58, 427 (2006) DOI PubMed. Review of pharmacology and clinical development: G. Mor et al., Curr. Opin. Investig. Drugs 7, 542-548 (2006) PubMed.

Chemical structure

Properties

Needles from methanol/benzene, mp 231° (dec). uv max: 245.5, 333 nm (log ε 4.20, 4.39)

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic