Streptonigrin

Streptonigrin

Names
Preferred IUPAC name 5-Amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylic acid
Other names Rufocromomycin, nigrin, bruneomycin [1]
Identifiers
CAS Number	3930-19-6  Y
3D model (JSmol)	Interactive image
ECHA InfoCard	100.021.366
PubChem CID	5298
UNII	261Q3JB310  Y
CompTox Dashboard (EPA)	DTXSID00960034
SMILES CC1=C(C(=C(N=C1C(=O)O)C2=NC3=C(C=C2)C(=O)C(=C(C3=O)N)OC)N)C4=C(C(=C(C=C4)OC)OC)O
Properties
Chemical formula	C25H22N4O8
Molar mass	506.471 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

A total synthesis of streptonigrin was reported in 2011. ^[3]

References

1. "Streptonigrin". NCI Drug Dictionary. National Cancer Institute.
2. 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.
3. 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. Bibcode:2011JAChS.13316418D. doi:10.1021/ja207835w. PMID   21942896.