The DOI matches its Crossref record; 4 of the 4 references it cites were found in a registry or an index.
Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design
Open accessAbstract
The electronic properties and relatively small size of fluorine endow it with considerable versatility as a bioisostere and it has found application as a substitute for lone pairs of electrons, the hydrogen atom, and the methyl group while also acting as a functional mimetic of the carbonyl, carbinol, and nitrile moieties. In this context, fluorine substitution can influence the potency, conformation, metabolism, membrane permeability, and P-gp recognition of a molecule and temper inhibition of the hERG channel by basic amines. However, as a consequence of the unique properties of fluorine, it features prominently in the design of higher order structural metaphors that are more esoteric in their conception and which reflect a more sophisticated molecular construction that broadens biological mimesis. In this Perspective, applications of fluorine in the construction of bioisosteric elements designed to enhance the in vitro and in vivo properties of a molecule are summarized.
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Cites
Spread of Artemisinin Resistance in Plasmodium falciparum Malaria
Ashley, E. A., Dhorda, M., Fairhurst, R. M., Amaratunga, C., Lim, P., Suon, S., Sreng, S., Anderson, J. M., Mao, S., Sam, B., et al. (2014) · New England Journal of Medicine · doi:10.1056/nejmoa1314981 · Cited by 2,205
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Correction of the F508del-CFTR protein processing defect in vitro by the investigational drug VX-809
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AG-221, a First-in-Class Therapy Targeting Acute Myeloid Leukemia Harboring Oncogenic IDH2 Mutations
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Cited by
U.S. FDA Approved Drugs from 2015–June 2020: A Perspective
Bhutani, P., Joshi, G., Raja, N., Bachhav, N., Rajanna, P. K., Bhutani, H., Paul, A. T., & Kumar, R. (2021) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.0c01786 · Cited by 815
Bioisosteres of the Phenyl Ring: Recent Strategic Applications in Lead Optimization and Drug Design
Subbaiah, M. A. M., & Meanwell, N. A. (2021) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.1c01215 · Cited by 710
Self-citationTay, N. E. S., Lehnherr, D., & Rovis, T. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00384 · Cited by 518
Xu, R., Wang, K., Rizzi, J. P., Huang, H., Grina, J. A., Schlachter, S. T., Wang, B., Wehn, P. M., Yang, H., Dixon, D. D., et al. (2019) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.9b00719 · Cited by 220
Wackett, L. P. (2022) · Microbial Biotechnology · doi:10.1111/1751-7915.13928 · Cited by 165
Metadata
- Authors
- Meanwell, N. A.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2018-02-05
- Volume
- 61
- Issue
- 14
- Pages
- 5822-5880
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2785609333
- Cited by
- 2,655
- References
- 4
- FWCI
- 79.88
- Type
- journal article
- Language
- en
- Open access
- green
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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.
