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A dideazatetrahydrofolate analog lacking a chiral center at C-6: N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5yl)ethyl[benzoyl]-L-glutamic acid is an inhibitor of thymidylate synthase
Open accessAbstract
N-[4-[2-(2-Amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5- yl)ethyl]benzoyl]-L-glutamic acid (15), prepared in five steps from 2-pivaloyl-7-deazaguanine, has been found to be an antitumor agent with its primary site of action at thymidylate synthase rather than purine synthesis. This compound appears to be a promising candidate for clinical evaluation.
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Cited by
Scagliotti, G. V., Parikh, P., von Pawel, J., Biesma, B., Vansteenkiste, J., Manegold, C., Serwatowski, P., Gatzemeier, U., Digumarti, R., Zukin, M., et al. (2008) · Journal of Clinical Oncology · doi:10.1200/jco.2007.15.0375 · Cited by 3,203
Phenotypic screening in cancer drug discovery — past, present and future
Moffat, J. G., Rudolph, J., & Bailey, D. (2014) · Nature Reviews Drug Discovery · doi:10.1038/nrd4366 · Cited by 507
Antifolates in cancer therapy: Structure, activity and mechanisms of drug resistance
Gonen, N., & Assaraf, Y. G. (2012) · Drug Resistance Updates · doi:10.1016/j.drup.2012.07.002 · Cited by 437
Standing the test of time: targeting thymidylate biosynthesis in cancer therapy
Wilson, P. M., Danenberg, P. V., Johnston, P. G., Lenz, H.-J., & Ladner, R. D. (2014) · Nature Reviews Clinical Oncology · doi:10.1038/nrclinonc.2014.51 · Cited by 388
Phenotypic drug discovery: recent successes, lessons learned and new directions
Vincent, F., Nueda, A., Lee, J., Schenone, M., Prunotto, M., & Mercola, M. (2022) · Nature Reviews Drug Discovery · doi:10.1038/s41573-022-00472-w · Cited by 348
Metadata
- Authors
- Taylor, E. C., Kuhnt, D., Shih, C., Rinzel, S. M., Grindey, G. B., Barredo, J., Jannatipour, M., & Moran, R. G.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1992-11
- Volume
- 35
- Issue
- 23
- Pages
- 4450-4454
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2020159902
- Cited by
- 254
- References
- 0
- FWCI
- 1.78
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: A dideazatetrahydrofolate analog lacking a chiral center at C-6: N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5yl)ethyl[benzoyl]-L-glutamic acid is an inhibitor of thymidylate synthase. https://app.cochat.ai/papers/10.1021/jm00101a023
- The paper
- Taylor, E. C., Kuhnt, D., Shih, C., Rinzel, S. M., Grindey, G. B., Barredo, J., Jannatipour, M., & Moran, R. G. (1992). A dideazatetrahydrofolate analog lacking a chiral center at C-6: N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5yl)ethyl[benzoyl]-L-glutamic acid is an inhibitor of thymidylate synthase. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm00101a023
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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