The DOI matches its Crossref record; 9 of the 9 references it cites were found in a registry or an index.
The “Cyclopropyl Fragment” is a Versatile Player that Frequently Appears in Preclinical/Clinical Drug Molecules
Open accessAbstract
Recently, there has been an increasing use of the cyclopropyl ring in drug development to transition drug candidates from the preclinical to clinical stage. Important features of the cyclopropane ring are, the (1) coplanarity of the three carbon atoms, (2) relatively shorter (1.51 Å) C–C bonds, (3) enhanced π-character of C–C bonds, and (4) C–H bonds are shorter and stronger than those in alkanes. The present review will focus on the contributions that a cyclopropyl ring makes to the properties of drugs containing it. Consequently, the cyclopropyl ring addresses multiple roadblocks that can occur during drug discovery such as (a) enhancing potency, (b) reducing off-target effects, (c) increasing metabolic stability, (d) increasing brain permeability, (e) decreasing plasma clearance, (f) contributing to an entropically more favorable binding to the receptor, (g) conformational restriction of peptides/peptidomimetics to prevent proteolytic hydrolysis, and (h) altering drug p K a to reduce its P-glycoprotein efflux ratio.
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Ivanov, I. I., McKenzie, B. S., Zhou, L., Tadokoro, C. E., Lepelley, A., Lafaille, J. J., Cua, D. J., & Littman, D. R. (2006) · Cell · doi:10.1016/j.cell.2006.07.035 · Cited by 5,145
DrugBank: a comprehensive resource for in silico drug discovery and exploration
Wishart, D. S. (2006) · Nucleic Acids Research · doi:10.1093/nar/gkj067 · Cited by 3,892
Honigberg, L. A., Smith, A. M., Sirisawad, M., Verner, E., Loury, D., Chang, B., Li, S., Pan, Z., Thamm, D. H., Miller, R. A., et al. (2010) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1004594107 · Cited by 1,561
Structural and functional diversity of native brain neuronal nicotinic receptors
Gotti, C., Clementi, F., Fornari, A., Gaimarri, A., Guiducci, S., Manfredi, I., Moretti, M., Pedrazzi, P., Pucci, L., & Zoli, M. (2009) · Biochemical Pharmacology · doi:10.1016/j.bcp.2009.05.024 · Cited by 469
Qian, F., Engst, S., Yamaguchi, K., Yu, P., Won, K.-A., Mock, L., Lou, T., Tan, J., Li, C., Tam, D., et al. (2009) · Cancer Research · doi:10.1158/0008-5472.can-08-4889 · Cited by 350
Distinct binding mode of multikinase inhibitor lenvatinib revealed by biochemical characterization.
Okamoto, K., Ikemori-Kawada, M., Jestel, A., von König, K., Funahashi, Y., Matsushima, T., Tsuruoka, A., Inoue, A., & Matsui, J. (2015) · ACS Medicinal Chemistry Letters · doi:10.1021/ml500394m · Cited by 285
Turner, J. R., Castellano, L. M., & Blendy, J. A. (2010) · The Journal of Pharmacology and Experimental Therapeutics · doi:10.1124/jpet.110.166280 · Cited by 88
Futatsugi, K., Kung, D. W., Orr, S. T. M., Cabral, S., Hepworth, D., Aspnes, G., Bader, S., Bian, J., Boehm, M., Carpino, P. A., et al. (2015) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.5b01006 · Cited by 88
Kozikowski, A. P., Eaton, J. B., Bajjuri, K. M., Chellappan, S. K., Chen, Y., Karadi, S., He, R., Caldarone, B., Manzano, M., Yuen, P., et al. (2009) · ChemMedChem · doi:10.1002/cmdc.200900079 · Cited by 36
Cited by
Kwon, K., Simons, R. T., Nandakumar, M., & Roizen, J. L. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00444 · Cited by 389
Wrobleski, S. T., Moslin, R., Lin, S., Zhang, Y., Spergel, S., Kempson, J., Tokarski, J. S., Strnad, J., Zupa-Fernandez, A., Cheng, L., et al. (2019) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.9b00444 · Cited by 382
A Survey of the Structures of US FDA Approved Combination Drugs
Das, P., Delost, M. D., Qureshi, M. H., Smith, D. T., & Njardarson, J. T. (2019) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.8b01610 · Cited by 312
Peese, K. M., Allard, C. W., Connolly, T., Johnson, B. L., Li, C., Patel, M., Sorensen, M. E., Walker, M. A., Meanwell, N. A., McAuliffe, B., et al. (2019) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.8b01473 · Cited by 39
Metadata
- Authors
- Talele, T. T.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-06-30
- Volume
- 59
- Issue
- 19
- Pages
- 8712-8756
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2422726141
- Cited by
- 1,023
- References
- 9
- FWCI
- 28.06
- Type
- journal article
- Language
- en
- Open access
- green
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- Talele, T. T. (2016). The “Cyclopropyl Fragment” is a Versatile Player that Frequently Appears in Preclinical/Clinical Drug Molecules. Journal of Medicinal Chemistry. https://doi.org/10.1021/acs.jmedchem.6b00472
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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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