The DOI matches its Crossref record; 24 of the 24 references it cites were found in a registry or an index.
A Library of Spirooxindoles Based on a Stereoselective Three-Component Coupling Reaction
Abstract
A collection of structurally complex and chemically diverse small molecules is a useful tool to explore cell circuitry. In this article, we report the split-pool synthesis of more than 3000 spirooxindoles on high capacity macrobeads. The key reaction to assemble the spirooxindole core stereoselectively is a Lewis acid variant of the Williams' three-component coupling. After formation, the skeleton was elaborated using Sonogashira couplings, amide forming reactions, and N-acylations of gamma-lactams. The final library was analyzed by sampling individual macrobeads and by using binomial confidence limits. It was determined that at least 82% of the library compounds should have better than 80% purity. To demonstrate the utility of our discovery process, a high-throughput chemical genetic modifier screen was performed using stock solutions of the resultant products. A number of positives were identified as enhancers of the cellular actions of latrunculin B, an actin polymerization inhibitor. Through resynthesis, we confirmed one of the positives and demonstrated that, in yeast cells, it has an EC50 in the sub-micromolar range.
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Cites
Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (1997) · Advanced Drug Delivery Reviews · doi:10.1016/s0169-409x(96)00423-1 · Cited by 11,385
Target-Oriented and Diversity-Oriented Organic Synthesis in Drug Discovery
Schreiber, S. L. (2000) · Science · doi:10.1126/science.287.5460.1964 · Cited by 2,568
Self-citationA Planning Strategy for Diversity‐Oriented Synthesis
Burke, M. D., & Schreiber, S. L. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200300626 · Cited by 1,493
Self-citationHoughten, R. A., Pinilla, C., Blondelle, S. E., Appel, J. R., Dooley, C. T., & Cuervo, J. H. (1991) · Nature · doi:10.1038/354084a0 · Cited by 1,326
General method for rapid synthesis of multicomponent peptide mixtures
FURKA, Á., SEBESTYÉN, F., ASGEDOM, M., & DIBÓ, G. (1991) · International Journal of Peptide and Protein Research · doi:10.1111/j.1399-3011.1991.tb00765.x · Cited by 1,155
Latrunculins: Novel Marine Toxins That Disrupt Microfilament Organization in Cultured Cells
Spector, I., Shochet, N. R., Kashman, Y., & Groweiss, A. (1983) · Science · doi:10.1126/science.6681676 · Cited by 750
Mechanism-Based Target Identification and Drug Discovery in Cancer Research
Gibbs, J. B. (2000) · Science · doi:10.1126/science.287.5460.1969 · Cited by 606
A general and expedient method for the solid-phase synthesis of 1,4-benzodiazepine derivatives
Bunin, B. A., & Ellman, J. A. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00053a067 · Cited by 443
The Asymmetric Total Synthesis of (+)- and (−)-Spirotryprostatin B
Sebahar, P. R., & Williams, R. M. (2000) · Journal of the American Chemical Society · doi:10.1021/ja001133n · Cited by 434
Dissecting glucose signalling with diversity-oriented synthesis and small-molecule microarrays
Kuruvilla, F. G., Shamji, A. F., Sternson, S. M., Hergenrother, P. J., & Schreiber, S. L. (2002) · Nature · doi:10.1038/416653a · Cited by 367
Self-citation
Cited by
Bencivenni, G., Wu, L., Mazzanti, A., Giannichi, B., Pesciaioli, F., Song, M., Bartoli, G., & Melchiorre, P. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200903192 · Cited by 448
Liu, Y., Nappi, M., Arceo, E., Vera, S., & Melchiorre, P. (2011) · Journal of the American Chemical Society · doi:10.1021/ja206517s · Cited by 398
Diastereomeric spirooxindoles as highly potent and efficacious MDM2 inhibitors
Zhao, Y., Liu, L., Sun, W., Lu, J., McEachern, D., Li, X., Yu, S., Bernard, D., Ochsenbein, P., Ferey, V., et al. (2013) · Journal of the American Chemical Society · doi:10.1021/ja3125417 · Cited by 234
Metadata
- Authors
- Lo, M. M.-C., Neumann, C. S., Nagayama, S., Perlstein, E. O., & Schreiber, S. L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-11-19
- Volume
- 126
- Issue
- 49
- Pages
- 16077-16086
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1968550772
- Cited by
- 276
- References
- 24
- FWCI
- 2.73
- Type
- journal article
- Language
- en
- Open access
- closed
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