Flavonoids from Phlomis tuberosa

Khokhorina, T A; Peshkova, V. A.; Glyzin, V. I.

doi:10.1007/bf00565810

Cited by 2 publications

(1 citation statement)

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“…for 1 of natural origin: 180–181°C [6]), 328–330 (lit. for 1′ of natural origin: 328–330°C [20]), 197–198°C and 171–183°C, respectively. HPLC and purity data for the known compounds 1 , 11 and 12 are as follows.…”

Section: Methodsmentioning

confidence: 99%

Direct Semi-Synthesis of the Anticancer Lead-Drug Protoapigenone from Apigenin, and Synthesis of Further New Cytotoxic Protoflavone Derivatives

et al. 2011

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Protoapigenone, a natural flavonoid possessing an unusual p-quinol moiety on its B-ring, is a novel prospective anticancer agent with low toxicity that is currently in development. The first economical, one-step synthesis of protoapigenone from apigenin is described on up to gram scale. 13 new 1′-O-alkylflavone analogs were also synthesized, either from apigenin or β-naphthoflavone. The in vitro cytotoxic activity of each compound was tested on six human cancer cell lines (HepG2, Hep3B, Ca9-22, A549, MCF-7 and MDA-MB-231). In the case of 1′-O-alkyl-protoapigenone derivatives, structure-activity relationships were found depending on the side-chain, and protoapigenone 1′-O-butyl ether was found to exert significantly stronger activity against three of the cell lines (Hep3B, MCF-7 and MDA-MB-231) than its non-substituted analog, protoapigenone itself. In contrast to this, all β-naphthoflavone derivatives bearing the same pharmacophore on their B-ring showed decreased cytotoxic activities when substituted with an O-alkyl side-chain at position 1′, comparing to that of the non-substituted compound.

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Section: Methodsmentioning

confidence: 99%