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SML1824

Sigma-Aldrich

GSK983

≥98% (HPLC)

Synonyme(s) :

GSK260983, N-[(1R)-6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-2-pyridinecarboxamide

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About This Item

Formule empirique (notation de Hill):
C18H16ClN3O
Numéro CAS:
827591-02-6
Poids moléculaire :
325.79
Numéro MDL:
MFCD28978021
Code UNSPSC :
51111800
ID de substance PubChem :
329826082
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Activité optique

[α]/D +175 to +195°, c = 1 in methylene chloride

Conditions de stockage

protect from light

Couleur

white to beige

Solubilité

DMSO: 10 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

ClC1=CC=C(NC2=C3CCC[C@H]2NC(C4=NC=CC=C4)=O)C3=C1

InChI

1S/C18H16ClN3O/c19-11-7-8-14-13(10-11)12-4-3-6-15(17(12)21-14)22-18(23)16-5-1-2-9-20-16/h1-2,5,7-10,15,21H,3-4,6H2,(H,22,23)

Clé InChI

WJQBOBGVBBZLJU-UHFFFAOYSA-N

Actions biochimiques/physiologiques

GSK983 blocks RNA virus replication with EC50 values of 10–40 nM, and also blocks cell proliferation. GSK983 acts by inhibition of dihydroorotate dehydrogenase (DHODH), necesssary for pyrimidine biosynthesis. Exogenous deoxycytidine was able to reduce GSK983 cytotoxicity, allowing cells to synthesize DNA, but still preventing RNA virus replication. GSK983 was active against dengue fever and Venezuelan equine encephalitis viruses.
GSK983 is a tetrahydrocarbazole or a broad spectrum antiviral lead compound. GSK983 acts by stimulating a subset of interferon-stimulated genes.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H315,H319

Classification des risques

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

GSK983: a novel compound with broad-spectrum antiviral activity.
Harvey R, et al.
Antiviral Research, 82(1), 1-11 (2009)
Kristjan S Gudmundsson et al.
Bioorganic & medicinal chemistry letters, 19(15), 4110-4114 (2009-06-27)
Synthesis of a series of tetrahydrocarbazole amides with potent activity against human papillomaviruses is described. Synthetic approaches allowing for variation of the substitution pattern of the tetrahydrocarbazole and the amide are outlined and resulting changes in antiviral activity and certain
Richard M Deans et al.
Nature chemical biology, 12(5), 361-366 (2016-03-29)
Broad-spectrum antiviral drugs targeting host processes could potentially treat a wide range of viruses while reducing the likelihood of emergent resistance. Despite great promise as therapeutics, such drugs remain largely elusive. Here we used parallel genome-wide high-coverage short hairpin RNA
Robert Harvey et al.
Antiviral research, 82(1), 1-11 (2009-02-04)
GSK983, a novel tetrahydrocarbazole, inhibits the replication of a variety of unrelated viruses in vitro with EC(50) values of 5-20 nM. Both replication of the adenovirus Ad-5 and the polyoma virus SV-40, and episomal maintenance of human papillomaviruses (HPV) and
Yajie Yu et al.
Cell death & disease, 12(9), 821-821 (2021-09-01)
Metabolic reprogramming is an integral part of the growth-promoting program driven by the MYC family of oncogenes. However, this reprogramming also imposes metabolic dependencies that could be exploited therapeutically. Here we report that the pyrimidine biosynthetic enzyme dihydroorotate dehydrogenase (DHODH)
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