J. Hadfield, A. McGown, J. Butler
Jan 18, 2000
Citations
0
Influential Citations
15
Citations
Journal
Molecules
Abstract
Department of Biological Sciences, Salford University, Salford, M5 4WT, UK*Author to whom correspondence should be addressed.Received: 2 November 1999 / Accepted: 12 January 2000 / Published: 18 January 2000Abstract: A short, high-yielding synthesis of the antitumour agent irisquinone (1) is de-scribed. The key steps are the palladium catalysed coupling reaction of dec-9-yn-1-ol withiodide (2) to form alkyne (3) and the Fremy’s salt oxidation of phenol (7).Keywords: Irisquinone; antitumour; Chinese medicine.IntroductionThe seeds of Iris pallasi (Iridaceae) have been used in Chinese folk medicine for the treatment ofvarious malignancies and for the treatment of metrorrhagia and vaginal discharge [1]. Irisquinone (1)has been isolated as an active principle [2] from the seed oil of I. pallasi and this 1,4-benzoquinone iseffective against cervical carcinoma, lymphosarcoma, hepatoma and Ehrlich ascites carcinoma (EAC)in mice [2, 3]. Irisquinone (1) damages nuclei of cells and inhibits [3] mitosis in cancer cells. Respira-tion of P388 cells is significantly inhibited by irisquinone (1) and mitochondrial damage to EAC cellshas been noted [4]. Furthermore, levels of cyclic guanosine monophosphate have been shown to in-crease [5] in plasma of tumour bearing mice after treatment with this quinone (1). These results sug-gest that the antitumour action of irisquinone (1) is likely to be different from that of other cytotoxic