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Synthesis and Biological Evaluation of Aromatic Analogues of Conduritol F, l-chiro-Inositol, and Dihydroconduritol F Structurally Related to the Amaryllidaceae Anticancer Constituents
journal contribution
posted on 2006-07-21, 00:00 authored by Artem S. Kireev, Oleg N. Nadein, Vincent J. Agustin, Nancy E. Bush, Antonio Evidente, Madhuri Manpadi, Marcia A. Ogasawara, Shiva K. Rastogi, Snezna Rogelj, Scott T. Shors, Alexander KornienkoPancratistatin is a potent anticancer natural product, whose clinical evaluation is hampered by the limited
natural abundance and the stereochemically complex structure undermining practical chemical preparation.
Fifteen aromatic analogues of conduritol F, l-chiro-inositol, and dihydroconduritol F that possess four
of the six pancratistatin stereocenters have been synthesized and evaluated for anticancer activity. These
compounds serve as truncated pancratistatin analogues lacking the lactam ring B, but retaining the crucial
C10a−C10b bond with the correct stereochemistry. The lack of activity of these compounds provides
further insight into pancratistatin's minimum structural requirements for cytotoxicity, particularly the
criticality of the intact phenanthridone skeleton. Significantly, these series provide rare examples of simple
aromatic conduritol and inositol analogues and, therefore, this study expands the chemistry and biology
of these important classes of compounds.
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phenanthridone skeletonC 10a bondConduritol Finositol analogueslactam ring BBiological Evaluationpancratistatin stereocenterschemical preparationpancratistatin analoguesDihydroconduritol F Structurally RelatedcompoundAmaryllidaceae Anticancer ConstituentsPancratistatinAromatic Analoguesconduritol Fdihydroconduritol Fanticancer activity
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