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Literature DB >> 14507217

Synthesis of novel C2-C3'N-linked macrocyclic taxoids by means of highly regioselective Heck macrocyclization.

Xudong Geng¹, Michael L Miller, Songnian Lin, Iwao Ojima.

Abstract

[reaction: see text] Novel C2-C3'N-linked macrocyclic taxoids are synthesized using intramolecular Heck reaction in the key step. Macrocyclization proceeds with high regioselectivity in good yield. Taxoids bearing an olefin moiety at C2 and an iodide at C3'N give exo-products exclusively. However, the endo-products are formed with up to 100% regioselectivity just by switching the positions of the olefin and the iodide moieties. Some of these macrocyclic taxoids are significantly cytotoxic.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2003 PMID： 14507217 DOI： 10.1021/ol0354627

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

10 in total

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4. Bridging converts a noncytotoxic nor-paclitaxel derivative to a cytotoxic analogue by constraining it to the T-Taxol conformation.

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Synthesis of novel C2-C3'N-linked macrocyclic taxoids by means of highly regioselective Heck macrocyclization.

Review 1. Drug discovery targeting cell division proteins, microtubules and FtsZ.

2. Evaluation of the tubulin-bound paclitaxel conformation: synthesis, biology, and SAR studies of C-4 to C-3' bridged paclitaxel analogues.

3. Rotational-echo double-resonance NMR distance measurements for the tubulin-bound Paclitaxel conformation.

4. Bridging converts a noncytotoxic nor-paclitaxel derivative to a cytotoxic analogue by constraining it to the T-Taxol conformation.

5. The bioactive Taxol conformation on beta-tubulin: experimental evidence from highly active constrained analogs.

6. Design, synthesis, and biological evaluation of novel C14-C3'BzN-linked macrocyclic taxoids.

Review 7. Recent advances in the study of the bioactive conformation of taxol.

8. Advances in the chemistry of β-lactam and its medicinal applications.

9. A natural love of natural products.

10. The quest for a simple bioactive analog of paclitaxel as a potential anticancer agent.