The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Influenza Neuraminidase Inhibitors Possessing a Novel Hydrophobic Interaction in the Enzyme Active Site: Design, Synthesis, and Structural Analysis of Carbocyclic Sialic Acid Analogues with Potent Anti-Influenza Activity
Abstract
The design, synthesis, and in vitro evaluation of the novel carbocycles as transition-state-based inhibitors of influenza neuraminidase (NA) are described. The double bond position in the carbocyclic analogues plays an important role in NA inhibition as demonstrated by the antiviral activity of 8 (IC50 = 6.3 microM) vs 9 (IC50 > 200 microM). Structure-activity studies of a series of carbocyclic analogues 6a-i identified the 3-pentyloxy moiety as an apparent optimal group at the C3 position with an IC50 value of 1 nM for NA inhibition. The X-ray crystallographic structure of 6h bound to NA revealed the presence of a large hydrophobic pocket in the region corresponding to the glycerol subsite of sialic acid. The high antiviral potency observed for 6h appears to be attributed to a highly favorable hydrophobic interaction in this pocket. The practical synthesis of 6 starting from (-)-quinic acid is also described.
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Cites
PROCHECK: a program to check the stereochemical quality of protein structures
Laskowski, R. A., MacArthur, M. W., Moss, D. S., & Thornton, J. M. (1993) · Journal of Applied Crystallography · doi:10.1107/s0021889892009944 · Cited by 24,581
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
Inhibition of neuraminidase activity by derivatives of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid
Meindl, P., Bodo, G., Palese, P., Schulman, J., & Tuppy, H. (1974) · Virology · doi:10.1016/0042-6822(74)90080-4 · Cited by 287
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Nicholson, K., Aoki, F., Osterhaus, A., Trottier, S., Carewicz, O., Mercier, C., Rode, A., Kinnersley, N., & Ward, P. (2000) · The Lancet · doi:10.1016/s0140-6736(00)02288-1 · Cited by 785
Antiviral agents active against influenza A viruses
De Clercq, E. (2006) · Nature Reviews Drug Discovery · doi:10.1038/nrd2175 · Cited by 668
Functional balance between haemagglutinin and neuraminidase in influenza virus infections
Wagner, R., Matrosovich, M., & Klenk, H. (2002) · Reviews in Medical Virology · doi:10.1002/rmv.352 · Cited by 608
Hayden, F. G., Treanor, J. J., Fritz, R. S., Lobo, M., Betts, R. F., Miller, M., Kinnersley, N., Mills, R. G., Ward, P., & Straus, S. E. (1999) · JAMA · doi:10.1001/jama.282.13.1240 · Cited by 550
Use of the Selective Oral Neuraminidase Inhibitor Oseltamivir to Prevent Influenza
Hayden, F. G., Atmar, R. L., Schilling, M., Johnson, C., Poretz, D., Paar, D., Huson, L., Ward, P., & Mills, R. G. (1999) · New England Journal of Medicine · doi:10.1056/nejm199910283411802 · Cited by 512
Metadata
- Authors
- Kim, C. U., Lew, W., Williams, M. A., Liu, H., Zhang, L., Swaminathan, S., Bischofberger, N., Chen, M. S., Mendel, D. B., Tai, C. Y., Laver, W. G., & Stevens, R. C.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1997-01-01
- Volume
- 119
- Issue
- 4
- Pages
- 681-690
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2003926950
- Cited by
- 1,100
- References
- 3
- FWCI
- 37.11
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Influenza Neuraminidase Inhibitors Possessing a Novel Hydrophobic Interaction in the Enzyme Active Site: Design, Synthesis, and Structural Analysis of Carbocyclic Sialic Acid Analogues with Potent Anti-Influenza Activity. https://app.cochat.ai/papers/10.1021/ja963036t
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- Kim, C. U., Lew, W., Williams, M. A., Liu, H., Zhang, L., Swaminathan, S., Bischofberger, N., Chen, M. S., Mendel, D. B., Tai, C. Y., Laver, W. G., & Stevens, R. C. (1997). Influenza Neuraminidase Inhibitors Possessing a Novel Hydrophobic Interaction in the Enzyme Active Site: Design, Synthesis, and Structural Analysis of Carbocyclic Sialic Acid Analogues with Potent Anti-Influenza Activity. Journal of the American Chemical Society. https://doi.org/10.1021/ja963036t
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
