Chemistry:Streptonigrin
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Streptonigrin is an aminoquinone antitumor and antibacterial antibiotic produced by Streptomyces flocculus.[1] It is an inhibitor of nitric oxide-dependent activation of soluble guanylyl cyclase.[2]
The first total synthesis of streptonigrin was published in 1980,[3] a different total synthesis with significantly higher yield was reported in 2011.[4]
References
- ↑ Cite error: Invalid
<ref>tag; no text was provided for refs namedNCI - ↑ Severina, I. S.; Pyatakova, N. V.; Postnikov, A. B.; Preobrazhenskaya, M. N.; Khropov, Y. V. (2004). "Antitumor antibiotic streptonigrin and its derivatives as inhibitors of nitric oxide-dependent activation of soluble guanylyl cyclase". European Journal of Pharmacology 483 (2–3): 127–132. doi:10.1016/j.ejphar.2003.10.018. PMID 14729099.
- ↑ Basha, Fatima Z.; Hibino, Satoshi; Kim, Deukjoon; Pye, Walter E.; Wu, Tai-Teh; Weinreb, Steven M. (1980). "Total synthesis of streptonigrin". Journal of the American Chemical Society 102 (11): 3962-3964. doi:10.1021/ja00531a054. https://doi.org/10.1021/ja00531a054.
- ↑ Donohoe, Timothy J.; Jones, Christopher R.; Barbosa, Luiz C. A. (2011). "Total Synthesis of (±)-Streptonigrin: De Novo Construction of a Pentasubstituted Pyridine using Ring-Closing Metathesis". Journal of the American Chemical Society 133 (41): 16418–16421. doi:10.1021/ja207835w. PMID 21942896. Bibcode: 2011JAChS.13316418D.
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