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Merck
CN

A76907

6-Thioguanine

98%

Synonym(s):

2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol

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About This Item

Empirical Formula (Hill Notation):
C5H5N5S
CAS Number:
154-42-7
Molecular Weight:
167.19
EC Number:
205-827-2
UNSPSC Code:
12352200
MDL number:
MFCD00233553
Beilstein/REAXYS Number:
157765

Key Documents

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InChI

1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)

InChI key

WYWHKKSPHMUBEB-UHFFFAOYSA-N

SMILES string

NC1=Nc2nc[nH]c2C(=S)N1

assay

98%

mp

≥300 °C (lit.)

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Biochem/physiol Actions

Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
15927DW
1602JH
08708LR
08521MS
00903AP

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Gustavo H B Maegawa et al.
The Journal of biological chemistry, 282(12), 9150-9161 (2007-01-24)
Late-onset GM2 gangliosidosis is composed of two related, autosomal recessive, neurodegenerative diseases, both resulting from deficiency of lysosomal, heterodimeric beta-hexosaminidase A (Hex A, alphabeta). Pharmacological chaperones (PC) are small molecules that can stabilize the conformation of a mutant protein, allowing
Elif Gürsoy et al.
European journal of medicinal chemistry, 42(3), 320-326 (2006-12-06)
A series of arylidenehydrazides (3a-3i) were synthesized from [6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetic acid hydrazide. The structures of new compounds were determined by analytical and spectral (IR, (1)H NMR, (13)C NMR, EIMS) methods. The synthesized compounds (3a-3i) were evaluated in the National Cancer Institute's
Jignesh M Doshi et al.
Journal of medicinal chemistry, 49(26), 7731-7739 (2006-12-22)
The structure-activity relationship studies of ethyl 2-amino-6-cyclopentyl-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (1, HA 14-1), an antagonist of the antiapoptotic Bcl-2 proteins, are reported. A series of analogues of 1 with varied functional groups at the 6-position of the chromene ring were synthesized. These candidates
Sonia G Das et al.
Journal of medicinal chemistry, 52(19), 5937-5949 (2009-09-12)
Rapid development of multiple drug resistance against current therapies is a major barrier in the treatment of cancer. Therefore, anticancer agents that can overcome acquired drug resistance in cancer cells are of great importance. Previously, we have demonstrated that ethyl
Alex M Aronov et al.
Journal of medicinal chemistry, 51(5), 1214-1222 (2008-02-22)
Small molecule protein kinase inhibitors are widely employed as biological reagents and as leads in the design of drugs for a variety of diseases. We investigated the phenomenon of kinase-likeness, i.e., the propensity of ligands to inhibit protein kinases, in
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