Synthesis and bioactivity of a brasilicardin a analogue featuring a simplified core
Abstract
An analogue 2 of Brasilicardin A, 1 (BraA), a potent immunosuppressive and cytotoxic agent, was synthesized in which the natural tricyclic skeleton was replaced with a synthetically more accessible substituted tetrahydronaphthalene core. BraA, this analogue (BraL), and cyclosporine A were tested for their ability to inhibit the proliferation of human T cells upon CD3/CD28 activation. Although BraL did not impact T cell activation over the dose range tested, this study shows the inhibitory activity of BraA on human T cells for the first time.
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THN-fused C3-spirooxindoles should possess good druglikeness because THN and spirooxindole derivatives are privileged drug-like architectures.
“We started with THN54, 55, 56, 57, 58, 59, 60, 61 and spirooxindole derivatives62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72 because they are privileged drug-like architectures, so the resulting THN-fused C3-spirooxindoles should possess good druglikeness (Fig. 2C).”
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Wang, B., Peng, F., Huang, W., Zhou, J., Zhang, N., Sheng, J., Haruehanroengra, P., He, G., & Han, B. (2020) · Acta Pharmaceutica Sinica B · doi:10.1016/j.apsb.2019.12.013 · Cited by 73 · see citing works
- Authors
- Jung, M. E., Chamberlain, B. T., Koch, P., & Niazi, K. R.
- Affiliations
- California NanoSystems Institute (US)
- NantWorks (United States) (US)
- Corresponding author
- Jung, Michael E.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2015-07-06
- Volume
- 17
- Issue
- 14
- Pages
- 3608-3611
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2222891198
- Cited by
- 20
- References
- 20
- Citations by year
- 2025: 1 · 2024: 2 · 2023: 1 · 2022: 1 · 2021: 3 · 2020: 1 · 2019: 2 · 2018: 3 · 2017: 5 · 2016: 1
- FWCI
- 1.30
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Organic Letters (publishedVersion)
- PubMed (publishedVersion)
- Funders
- California Capital
- NantWorks LLC
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Biological Activity of Diterpenoids and Biflavonoids
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Natural product bioactivities and synthesis
- Keywords
- tricyclic skeleton, immunosuppressants, cytotoxic drugs, T cell proliferation inhibition, cyclosporine, total synthesis
- MeSH terms
- Aminoglycosides, Antineoplastic Agents, Humans, Immunosuppressive Agents, Naphthalenes, T-Lymphocytes, Molecular Structure, Cyclosporine, CD3 Complex, CD28 Antigens
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