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222429

Sigma-Aldrich

5-Methylisatin

95%

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Synonym(s):
5-Methylindole-2,3-dione, NSC 9398
Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
Molecular Weight:
161.16
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

form

solid

mp

180 °C (dec.) (lit.)

solubility

methanol: soluble 25 mg/mL, clear to slightly hazy, orange to red

SMILES string

Cc1ccc2NC(=O)C(=O)c2c1

InChI

1S/C9H7NO2/c1-5-2-3-7-6(4-5)8(11)9(12)10-7/h2-4H,1H3,(H,10,11,12)

InChI key

VAJCSPZKMVQIAP-UHFFFAOYSA-N

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1 of 4

This Item
143510N17807663190
5-Methylisatin 95%

222429

5-Methylisatin

5-Hydroxyindole-2-carboxylic acid ≥96.5%

143510

5-Hydroxyindole-2-carboxylic acid

5-Nitroisatin 97%

N17807

5-Nitroisatin

Ethyl 5-methylindole-2-carboxylate 97%

663190

Ethyl 5-methylindole-2-carboxylate

solubility

methanol: soluble 25 mg/mL, clear to slightly hazy, orange to red

solubility

chloroform/ethanol (1:1): soluble 50 mg/mL, clear to slightly hazy, yellow to brown

solubility

-

solubility

-

form

solid

form

powder

form

powder

form

solid

mp

180 °C (dec.) (lit.)

mp

249 °C (dec.) (lit.)

mp

251 °C (dec.) (lit.)

mp

160-164 °C

General description

5-Methylisatin is an inhibitor of atrial natriuretic peptide (ANP) receptor coupled with guanylyl cyclase (GC).

Application

5-Methylisatin was used as an internal standard during the determination of isatin (indole-2, 3-
dione) in body fluids by capillary column gas chromatography-mass spectrometry (GC—MS).
Reactant for preparation of:
  • Antimycobacterial agents
  • Promoters of central nervous system (CNS) depression in mice
  • Inhibitors of TAK1 kinase
  • Anti-human immunodeficiency virus (HIV) agent
  • Potent herpes simplex virus (HSV) inhibitors
  • Antimicrobial agents
  • IKKβ inhibitors
  • Potential drug to combat human immunodeficiency virus-tuberculosis (HIV-TB) coinfection
  • Cyclooxygenase 1/2 (COX-1/2) and 5-lipoxygenase (5-LOX) inhibitors
  • Antibacterial and anticancer agents

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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Yong Wang et al.
Bioorganic chemistry, 97, 103710-103710 (2020-03-09)
Moenomycin A, the well-known natural product inhibitor of peptidoglycan glycosyltransferase (PGT), is a large amphiphilic molecule of molecular mass of 1583 g/mol and its bioavailablity as a drug is relatively poor. In searching for small-molecule ligands with high inhibition ability targeting
A E Medvedev et al.
Biochemical pharmacology, 57(8), 913-915 (1999-03-23)
Isatin is an endogenous indole and an inhibitor of atrial natriuretic peptide (ANP) receptors coupled with particulate guanylyl cyclase (GC). In this study, several isatin analogues were tested as inhibitors of ANP-stimulated GC in rat brain and heart membranes. None
M Dorneanu et al.
Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi, 100(1-2), 167-171 (1996-01-01)
This paper presents the synthesis of six hydrazones obtained by treating 5-methyl-isatin or 1-morpholino methyl-5-methyl-isatin with 3-(R-phenyl)-6-hydrazino-pyridazine (R = OCH3, Cl, Br) and two complex combination with copper, derived from 3-(p-anisyl-pyridazinyl)-hydrazone-5-methyl-indoline-2- one. The structure of the new compounds was confirmed
J M Halket et al.
Journal of chromatography, 562(1-2), 279-287 (1991-01-02)
A simple procedure based upon capillary column gas chromatography-mass spectrometry (GC-MS) is described for the detection and determination of isatin (indole-2,3-dione) in body fluids and tissues. After addition of 5-methylisatin as internal standard to urine or tissue homogenates, organic extracts

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