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
Beilstein Reference	599390
ChEBI	CHEBI:9287
ChEMBL	ChEMBL11417
ChemSpider	10207545
ECHA InfoCard	100.021.366
EC Number	223-501-8
Gmelin Reference	1240693
KEGG	C02081
PubChem CID	5298
UNII	261Q3JB310  Y
CompTox Dashboard (EPA)	DTXSID00960034
InChI InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34) Key: PVYJZLYGTZKPJE-UHFFFAOYSA-N
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
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300
Precautionary statements	P264, P270, P301+P316, P321, P330, P405, P501
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]

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

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. 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.
4. 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.