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Publication Details
AFRICAN RESEARCH NEXUS
SHINING A SPOTLIGHT ON AFRICAN RESEARCH
chemistry
Synthesis of structurally simplified analogues of pancratistatin: Truncation of the cyclitol ring
Journal of Organic Chemistry, Volume 74, No. 18, Year 2009
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Description
(Chemical Equation Presented) Pancratistatin is a phenanthridone-type natural product isolated from several plants of the Amaryllidaceae family. Its potent antiproliferative, antivascular, antiviral, and antiparasitic properties have attracted the attention of synthetic, biological, and medicinal chemists. Pancratistatin's low natural availability and complex structure have steered many of these research projects toward the preparation of its simplified synthetic analogues with useful levels of activity. In this work we have developed synthetic chemistry aimed at the preparation of pancratistatin analogues with a truncated cyclitol portion of the molecule. The described synthetic pathways are based on a highly anti-diastereoselective arylcuprate conjugate addition to γ-alkoxy-α,β-enoates and syn-selective azidation at the α-position of ester enolates. Analogues with the formally cleaved C3-C4 bond, and thus containing an open ring C, as well as a compound containing a truncated lactol moiety in lieu of the cyclitol,were prepared. Several of the analogues exhibited weak antiproliferative activity, with the highest potency observed in the case of the lactol analogue. From these results implications for the design of future pancratistatin analogues are discussed. Furthermore, the synthetic pathways can be used to construct pancratistatin-mimetic libraries, in which the cyclitol moiety is replaced by other cyclic motifs. © 2009 American Chemical Society.
Authors & Co-Authors
Manpadi, Madhuri
United States, Socorro
New Mexico Institute of Mining and Technology
Kireev, Artem S.
United States, Socorro
New Mexico Institute of Mining and Technology
Magedov, Igor V.
United States, Socorro
New Mexico Institute of Mining and Technology
Altig, Jeff A.
United States, Socorro
New Mexico Institute of Mining and Technology
Tongwa, Paul
United States, Las Vegas
New Mexico Highlands University
Antipin, Mikhail Yu
United States, Las Vegas
New Mexico Highlands University
Russian Federation, Moscow
A.n.nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Evidente, Antonio
Italy, Naples
Università Degli Studi Di Napoli Federico Ii
van Otterlo, Willem A. L.
South Africa, Johannesburg
University of the Witwatersrand
Kornienko, Alexander V.
United States, Socorro
New Mexico Institute of Mining and Technology
Statistics
Citations: 23
Authors: 9
Affiliations: 5
Identifiers
Doi:
10.1021/jo901494r
ISSN:
00223263