Synthesis and structure revision of tyroscherin, and bioactivities of its stereoisomers against IGF-1-dependent tumor cells
@article{Ishigami2009SynthesisAS, title={Synthesis and structure revision of tyroscherin, and bioactivities of its stereoisomers against IGF-1-dependent tumor cells}, author={K. Ishigami and R. Katsuta and Chi{\'e} Shibata and Y. Hayakawa and H. Watanabe and T. Kitahara}, journal={Tetrahedron}, year={2009}, volume={65}, pages={3629-3638} }
Synthesis of the proposed structure of tyroscherin, a growth inhibitor of IGF-1-dependent cancer cells, was succeeded by one-pot Julia coupling. However, spectral data of the synthetic compound were not identical with those of natural tyroscherin. The stereochemistry of tyroscherin is revised to be 2S,3R,8R,10R by syntheses of stereoisomers. Synthetic tyroscherin showed more potent activity than its stereoisomers against IGF-1-dependent cancer cells.
17 Citations
Unexpected stereochemical tolerance for the biological activity of tyroscherin.
- Chemistry, Medicine
- Bioorganic & medicinal chemistry
- 2011
- 3
Synthesis of (2RS,8R,10R)-YM-193221 and an Improved Approach to Tyroscherin, Bioactive Natural Compounds from Pseudallescheria sp.
- Chemistry, Medicine
- Bioscience, biotechnology, and biochemistry
- 2010
- 1
Synthesis and biological evaluation of tyrosine modified analogues of the α4β7 integrin inhibitor biotin-R₈ERY.
- Chemistry, Medicine
- Bioorganic & medicinal chemistry
- 2012
- 12
Alkylative ring opening of N-methylaziridinium ions and a formal synthesis of tyroscherin.
- Chemistry, Medicine
- Organic letters
- 2012
- 27
- PDF
N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds
- Chemistry, Medicine
- Beilstein journal of organic chemistry
- 2019
- PDF
The site-specific basicity of thyroid hormones and their precursors as regulators of their biological functions.
- Chemistry, Medicine
- Journal of pharmaceutical and biomedical analysis
- 2012
- 9
References
SHOWING 1-10 OF 10 REFERENCES
Synthesis and structure revision of tyroscherin, a growth inhibitor of IGF-1-dependent tumor cells
- Chemistry
- 2008
- 12
Structure of tyroscherin, an antitumor antibiotic against IGF-1-dependent cells from Pseudallescheria sp.
- Chemistry, Medicine
- The Journal of antibiotics
- 2004
- 18
- PDF
Approach toward the total synthesis of orevactaene. 2. Convergent and stereoselective synthesis of the C18-C31 domain of orevactaene. Evidence for the relative configuration of the side chain.
- Chemistry, Medicine
- The Journal of organic chemistry
- 2002
- 36
Effect of oxygen substituents on two‐ and three‐bond carbon–proton spin–spin coupling constants
- Chemistry
- 2000
- 25