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85885

Streptonigrin from Streptomyces flocculus

≥98.0% (TLC)

Synonym(s):

Bruneomycin, Nigrin

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About This Item

Empirical Formula (Hill Notation):
C25H22N4O8
CAS Number:
3930-19-6
Molecular Weight:
506.46
EC Number:
223-501-8
UNSPSC Code:
12352200
MDL number:
MFCD00063401
Beilstein/REAXYS Number:
599390
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assay

≥98.0% (TLC)

antibiotic activity spectrum

viruses

mode of action

DNA synthesis | interferes

storage temp.

2-8°C

SMILES string

COc1ccc(c(O)c1OC)-c2c(C)c(nc(c2N)-c3ccc4C(=O)C(OC)=C(N)C(=O)c4n3)C(O)=O

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)

InChI key

PVYJZLYGTZKPJE-UHFFFAOYSA-N

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 1 Oral

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Guido Verniest et al.
The Journal of organic chemistry, 75(2), 424-433 (2009-12-19)
ABC analogues of the antitumor antibiotic lavendamycin, which contain the key metal chelation site and redox-active quinone unit essential for biological activity, were prepared via the palladium(0)-catalyzed cross-coupling reaction of various 2-haloheteroaromatics with 2-stannylated pyridines and quinolines. Using the Stille
Dylan B England et al.
Organic letters, 10(16), 3631-3634 (2008-07-17)
A series of N-propargylindole-2-carboxamides were found to undergo a AuCl 3-catalyzed cycloisomerization to give beta-carbolinones in high yield. The corresponding beta-chlorocarboline derivative was prepared and used for Pd(0)-catalyzed cross-coupling chemistry directed toward the synthesis of lavendamycin analogues.
Franco Rongioletti et al.
Journal of the American Academy of Dermatology, 69(1), 66-72 (2013-03-05)
Scleromyxedema is associated with a monoclonal gammopathy and other comorbidities. Its prognostic and therapeutic features are poorly documented because most reports deal with single cases or small series. We sought to describe the characteristics of patients with scleromyxedema regarding demographics
Timothy J Donohoe et al.
Journal of the American Chemical Society, 133(41), 16418-16421 (2011-09-29)
The synthesis of the potent antitumor agent (±)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted
Wen Cai et al.
Bioorganic & medicinal chemistry, 18(5), 1899-1909 (2010-02-13)
A series of lavendamycin analogues with two, three or four substituents at the C-6, C-7 N, C-2', C-3' and C-11' positions were synthesized via short and efficient methods and evaluated as potential NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor agents. The compounds were
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