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Literature DB >> 16183280

A synthesis of 3-deoxydihydrolycoricidine: refinement of a structurally minimum pancratistatin pharmacophore.

James McNulty¹, Vladimir Larichev, Siyaram Pandey.

Abstract

The synthesis of 3-deoxydihydrolycoricidine, a key element toward elucidation of the pancratistatin anticancer pharmacophore, is described. Biological evaluation of this compound showed it to be significantly less active against tumor cells than pancratistatin. In addition to those features previously identified, the requirement of a 2,3,4-triol functionalized ring-C is now definitely established as the minimum pharmacophoric element for potent anticancer activity.

Entities: Chemical Disease

Mesh：

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Year: 2005 PMID： 16183280 DOI： 10.1016/j.bmcl.2005.08.024

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

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Cited

17 in total

1. Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.

Authors: Jonathan Collins; Uwe Rinner; Michael Moser; Tomas Hudlicky; Ion Ghiviriga; Anntherese E Romero; Alexander Kornienko; Dennis Ma; Carly Griffin; Siyaram Pandey
Journal: J Org Chem Date: 2010-05-07 Impact factor: 4.354

2. A novel synthetic C-1 analogue of 7-deoxypancratistatin induces apoptosis in p53 positive and negative human colorectal cancer cells by targeting the mitochondria: enhancement of activity by tamoxifen.

Authors: Dennis Ma; Phillip Tremblay; Kevinjeet Mahngar; Pardis Akbari-Asl; Jonathan Collins; Tomas Hudlicky; James McNulty; Siyaram Pandey
Journal: Invest New Drugs Date: 2011-04-15 Impact factor: 3.850

A synthesis of 3-deoxydihydrolycoricidine: refinement of a structurally minimum pancratistatin pharmacophore.

1. Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.

2. A novel synthetic C-1 analogue of 7-deoxypancratistatin induces apoptosis in p53 positive and negative human colorectal cancer cells by targeting the mitochondria: enhancement of activity by tamoxifen.

3. Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation.

Review 4. Chemistry, biology, and medicinal potential of narciclasine and its congeners.

5. Unnatural C-1 homologues of pancratistatin - Synthesis and promising biological activities.

6. TOTAL SYNTHESES OF PANCRATISTATIN. A REVIEW.

7. Synthesis and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide.

8. Amaryllidaceae isocarbostyril alkaloids and their derivatives as promising antitumor agents.

9. Synthesis of structurally simplified analogues of pancratistatin: truncation of the cyclitol ring.

10. Synthesis and biological evaluation of 10-benzyloxy-Narciclasine.