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Dihydropyrancarboxamides Related to Zanamivir: A New Series of Inhibitors of Influenza Virus Sialidases. 1. Discovery, Synthesis, Biological Activity, and Structure−Activity Relationships of 4-Guanidino- and 4-Amino-4 H-pyran-6-carboxamides
Open accessAbstract
4-Amino- and 4-guanidino-4H-pyran-6-carboxamides 4 and 5 related to zanamivir (GG167) are a new class of inhibitors of influenza virus sialidases. Structure--activity studies reveal that, in general, secondary amides are weak inhibitors of both influenza A and B viral sialidases. However, tertiary amides, which contain one or more small alkyl groups, show much greater inhibitory activity, particularly against the influenza A virus enzyme. The sialidase inhibitory activities of these compounds correlate well with their in vitro antiviral efficacy, and several of the most potent analogues displayed useful antiviral activity in vivo when evaluated in a mouse model of influenza A virus infection. Carboxamides which were highly active sialidase inhibitors in vitro also showed good antiviral activity in the mouse efficacy model of influenza A infection when administered intranasally but displayed modest activity when delivered by the intraperitoneal route.
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Cites
Rational design of potent sialidase-based inhibitors of influenza virus replication
von Itzstein, M., Wu, W.-Y., Kok, G. B., Pegg, M. S., Dyason, J. C., Jin, B., Van Phan, T., Smythe, M. L., White, H. F., Oliver, S. W., et al. (1993) · Nature · doi:10.1038/363418a0 · Cited by 1,862
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Resistance of influenza viruses to neuraminidase inhibitors — a review
MCKIMMBRESCHKIN, J. (2000) · Antiviral Research · doi:10.1016/s0166-3542(00)00103-0 · Cited by 320
Zheng, B.-J., Chan, K.-W., Lin, Y.-P., Zhao, G.-Y., Chan, C., Zhang, H.-J., Chen, H.-L., Wong, S. S. Y., Lau, S. K. P., Woo, P. C. Y., et al. (2008) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0711942105 · Cited by 302
Metadata
- Authors
- Smith, P. W., Sollis, S. L., Howes, P. D., Cherry, P. C., Starkey, I. D., Cobley, K. N., Weston, H., Scicinski, J., Merritt, A., Whittington, A., Wyatt, P., Taylor, N., Green, D., Bethell, R., Madar, S., Fenton, R. J., Morley, P. J., Pateman, T., & Beresford, A.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1998-02-18
- Volume
- 41
- Issue
- 6
- Pages
- 787-797
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2167289817
- Cited by
- 342
- References
- 1
- FWCI
- 6.13
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Dihydropyrancarboxamides Related to Zanamivir: A New Series of Inhibitors of Influenza Virus Sialidases. 1. Discovery, Synthesis, Biological Activity, and Structure−Activity Relationships of 4-Guanidino- and 4-Amino-4 H-pyran-6-carboxamides. https://app.cochat.ai/papers/10.1021/jm970374b
- The paper
- Smith, P. W., Sollis, S. L., Howes, P. D., Cherry, P. C., Starkey, I. D., Cobley, K. N., Weston, H., Scicinski, J., Merritt, A., Whittington, A., Wyatt, P., Taylor, N., Green, D., Bethell, R., Madar, S., Fenton, R. J., Morley, P. J., Pateman, T., & Beresford, A. (1998). Dihydropyrancarboxamides Related to Zanamivir: A New Series of Inhibitors of Influenza Virus Sialidases. 1. Discovery, Synthesis, Biological Activity, and Structure−Activity Relationships of 4-Guanidino- and 4-Amino-4 H-pyran-6-carboxamides. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm970374b
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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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