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E31804

Sigma-Aldrich

Ethyl 5-hydroxy-2-methylindole-3-carboxylate

97%

Synonym(s):

NSC 405600

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About This Item

Empirical Formula (Hill Notation):
C12H13NO3
CAS Number:
7598-91-6
Molecular Weight:
219.24
EC Number:
231-507-7
MDL number:
MFCD00044575
UNSPSC Code:
12352100
PubChem Substance ID:
24894500
NACRES:
NA.22

assay

97%

mp

205-208 °C (lit.)

SMILES string

CCOC(=O)c1c(C)[nH]c2ccc(O)cc12

InChI

1S/C12H13NO3/c1-3-16-12(15)11-7(2)13-10-5-4-8(14)6-9(10)11/h4-6,13-14H,3H2,1-2H3

InChI key

BSNHKSUAAMJXBB-UHFFFAOYSA-N

Application

Reactant for preparation of:
  • Potential anti-inflammatory and analgesic agents[1]
  • Histamine-3 receptor inverse agonists for the treatment of obesity[2]
  • Tubulin Polymerization Inhibitors[3]
  • 4,7-dioxoindole-3-methyl prodrugs[4]
  • Antagonists at M4 muscarinic receptors[5]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
STBH6141
STBD9640V
STBD8595V
06784V
06784

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Thomas M Böhme et al.
Journal of medicinal chemistry, 45(14), 3094-3102 (2002-06-28)
Previously, we reported on PD 102807 (41) as being the most selective synthetic M(4) muscarinic antagonist identified to date. Synthesized analogues of 41 showed no improvement in affinity and selectivity at that time. However, several newly synthesized compounds exhibit a
Badiger, J.; et al.
ARKIVOC (Gainesville, FL, United States), 217-217 (2009)
Ferrer, S.; et al.
Tetrahedron, 59, 3445-3445 (2003)
Pascale David Pierson et al.
Journal of medicinal chemistry, 52(13), 3855-3868 (2009-05-22)
Obesity is a major risk factor in the development of conditions such as hypertension, hyperglycemia, dyslipidemia, coronary artery disease, and cancer. Several pieces of evidence across different species, including primates, underscore the implication of the histamine 3 receptor (H(3)R) in
Jing-Ping Liou et al.
Journal of medicinal chemistry, 51(14), 4351-4355 (2008-07-01)
1-Aroylindoline, 1-aroyl-1,2,3,4-tetrahydroquinoline, and 1-aroylindole derivatives were synthesized and evaluated for anticancer activity. The 4-amino and 4-hydroxy-1-aroylindoles 26 and 27 with IC 50 of 0.9 and 0.6 microM, respectively, exhibited antitubulin activity superior or comparable to that of colchicine and combretastatin

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