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Literature DB >> 10571173

Conformationally restricted paclitaxel analogues: macrocyclic mimics of the "hydrophobic collapse" conformation.

T C Boge¹, Z J Wu, R H Himes, D G Vander Velde, G I Georg.

Abstract

Conformationally restricted macrocyclic analogues of paclitaxel were prepared, by connecting the 3'-phenyl group and the 2-benzoate moiety with two-atom tethers to mimic the "hydrophobic collapse" paclitaxel conformation. The analogues did not show activity in a tubulin assembly assay.

Entities: Chemical

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Year: 1999 PMID： 10571173 DOI： 10.1016/s0960-894x(99)00522-3

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

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Cited

10 in total

1. The binding conformation of Taxol in beta-tubulin: a model based on electron crystallographic density.

Authors: J P Snyder; J H Nettles; B Cornett; K H Downing; E Nogales
Journal: Proc Natl Acad Sci U S A Date: 2001-04-17 Impact factor: 11.205

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

Authors: Thota Ganesh; Chao Yang; Andrew Norris; Tom Glass; Susan Bane; Rudravajhala Ravindra; Abhijit Banerjee; Belhu Metaferia; Shala L Thomas; Paraskevi Giannakakou; Ana A Alcaraz; Ami S Lakdawala; James P Snyder; David G I Kingston
Journal: J Med Chem Date: 2007-01-31 Impact factor: 7.446

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

Authors: Younkee Paik; Chao Yang; Belhu Metaferia; Shoubin Tang; Susan Bane; Rudravajhala Ravindra; Natasha Shanker; Ana A Alcaraz; Scott A Johnson; Jacob Schaefer; Robert D O'Connor; Lynette Cegelski; James P Snyder; David G I Kingston
Journal: J Am Chem Soc Date: 2007-01-17 Impact factor: 15.419

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

Authors: Shoubin Tang; Chao Yang; Peggy Brodie; Susan Bane; Rudravajhala Ravindra; Shubhada Sharma; Yi Jiang; James P Snyder; David G I Kingston
Journal: Org Lett Date: 2006-08-31 Impact factor: 6.005

Conformationally restricted paclitaxel analogues: macrocyclic mimics of the "hydrophobic collapse" conformation.

1. The binding conformation of Taxol in beta-tubulin: a model based on electron crystallographic density.

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. Synthesis of novel sterically demanding carbo- and heterocyclic beta-ketoesters.

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

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

Review 8. Modifications of human carboxylesterase for improved prodrug activation.

9. A natural love of natural products.

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