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21 results on '"Pinkerton, David M."'

6. Synthesis of the seco‐Limonoid BCD Ring System Identifies a Hsp90 Chaperon Machinery (p23) Inhibitor.

Author

Pinkerton, David M., Chow, Sharon, Eisa, Nada H., Kainth, Kashish, Vanden Berg, Timothy J., Burns, Jed M., Guddat, Luke W., Savage, G. Paul, Chadli, Ahmed, and Williams, Craig M.

Subjects
*HEAT shock proteins, *MOLECULAR chaperones, *LIMONOIDS, *ANTINEOPLASTIC agents, *STRUCTURE-activity relationships, *DOUBLE bonds
Abstract

D‐Ring‐seco‐limonoids (tetranortriterpenoids), such as gedunin and xylogranin B display anti‐cancer activity, acting via inhibition of Hsp90 and/or associated chaperon machinery (e.g. p23). Despite this, these natural products have received relatively little attention, both in terms of an enabling synthetic approach (which would allow access to derivatives), and as a consequence their structure–activity relationship (SAR). Disclosed herein is a generally applicable synthetic route to the BCD ring system of the seco‐D‐ring double bond containing limonoids. Furthermore, cell based assays revealed the first skeletal fragment that exhibited inhibition of the p23 enzyme at a level which was equipotent to that of gedunin, despite being much less structurally complex. The first synthetic route to the BCD ring system of the seco‐D‐ring limonoids has been devised. A synthetic intermediate displayed an equipotent p23 enzyme inhibitory effect to that of the more complex gedunin. [ABSTRACT FROM AUTHOR]

Published
2019
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15. Antimicrobial and Cytotoxic Activities of Synthetically Derived Tambjamines C and E - J, BE-18591, and a Related Alkaloid from the Marine Bacterium Pseudoalteromonas tunicata

Author

Pinkerton, David M., primary, Banwell, Martin G., additional, Garson, Mary J., additional, Kumar, Naresh, additional, de Moraes, Manoel Odorico, additional, Cavalcanti, Bruno C., additional, Barros, Francisco W. A., additional, and Pessoa, Cláudia, additional

Published
2010
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16. (+)-Hexacyclinol

Author

Pinkerton, David M., primary, Banwell, Martin G., additional, and Willis, Anthony C., additional

Published
2010
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21. Gaining Synthetic Appreciation for the Gedunin ABC Ring System.

Author

Pinkerton DM, Vanden Berg TJ, Bernhardt PV, and Williams CM

Abstract

Gedunin, first isolated in 1960, displays a remarkable range of biological activity, but has yet to receive dedicated synthetic attention from a ground up construction perspective. Presented herein is a successfully executed approach to the fully functionalized ABC ring system of this challengingly complex natural product., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2017
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