20876-36-2

Basic information

• Product Name: 5-Aminooxindole
• Synonyms: 5-amino-3,3a-dihydro-1H-indol-2(7aH)-one;REF DUPL: 5-Amino-2-oxindole;5-Amino-1,3-dihydro-indol...;5-amino-1,3-dihydro-2H-indol-2-one(SALTDATA: HCl);5-Amino-1,3-dihydro-2H-indol-2-one, 5-Aminoindolin-2-one;5-amino-2-indolinone;TIMTEC-BB SBB010120;CHEMBRDG-BB 4006397
• CAS NO: 20876-36-2
• Molecular Formula: C₈H₈N₂O
• Molecular Weight: 148.16
• Product Categories: Amines;blocks;IndolesOxindoles;Indoline & Oxindole;Indoles
• Mol File: 20876-36-2.mol
• Article Data: 45

Chemical Properties

• Melting Point: 182-186°C
• Boiling Point: 416.8 °C at 760 mmHg
• Flash Point: 205.8 °C
• Appearance: /
• Density: 1.307 g/cm³
• Vapor Pressure: 3.73E-07mmHg at 25°C
• Refractive Index: 1.653
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.91±0.20(Predicted)
• CAS DataBase Reference: 5-Aminooxindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Aminooxindole(20876-36-2)
• EPA Substance Registry System: 5-Aminooxindole(20876-36-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 20876-36-2(Hazardous Substances Data)

Usage

Uses

5-Amino-2-indolinone is useful in the synthesis of anticancer drugs, Cyclin dependent kinase inhibitors and spleen tyrosine kinase (Syk) inhibitors.

InChI:InChI=1/C8H8N2O/c9-6-1-2-7-5(3-6)4-8(11)10-7/h1-3H,4,9H2,(H,10,11)

Upstream product

• 611-09-6 5-nitroisatin 
• 42816-53-5 5-Aminoisatin 
• 6146-52-7 5-nitroindole 
• 59-48-3 2-oxoindole 
• 20870-79-5 5-nitrooxindole 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 1171584-41-0 1-(4-chlorophenyl)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)-urea 
• 1170790-72-3 1-(2-oxo-2,3-dihydro-1H-indol-5-yl)-3-phenylurea 
• 1172464-50-4 1-(4-methoxyphenyl)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)-urea 
• 1427789-19-2 C₁₃H₁₀N₂O₂ 
• 1360449-47-3 (5-fluoro-2-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)pyrimidin-4-yl]ethyl}phenyl)acetonitrile 
• 1360449-50-8 1-(2-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)pyrimidin-4-yl]ethyl}-4-trifluoromethylphenyl)cyclobutanecarbonitrile 
• 1360460-87-2 5-(4-phenethyl-5-trifluoromethylpyrimidin-2-ylamino)-1,3-dihydro-indol-2-one 
• 1360450-91-4 5-{4-[2-(4-fluorophenyl)ethyl]-5-trifluoromethylpyrimidin-2-ylamino}-1,3-dihydro-indol-2-one 

Relevant articles and documents

Design, synthesis and biological evaluation of indole-2-one derivatives as potent BRD4 inhibitors

Bromodomain protein 4 (BRD4) plays a crucial role in transcriptional regulation and is considered to be a viable drug target for cancer treatment. Herein, we designed and synthesized a series of indole-2-one derivatives through scaffold hopping drug desig

Synthesis of novel 3,5-disubstituted-2-oxindole derivatives as antitumor agents against human nonsmall cell lung cancer

This study was aimed at investigating the antitumor activity of novel 2-oxindole derivatives against a well-characterized human nonsmall cell lung cancer (NSCLC) cell line. Test compounds produced an antiproliferative activity in the low micromolar/submicromolar range of concentrations and significantly induced typical apoptotic morphology with cell shrinkage, nuclear condensation and fragmentation, and rupture of cells into debris in a relatively low percentage of A549 cells. Cell cycle arrest occurred at the G1/S phase (1a and 2), and Akt phosphorylation was significantly inhibited at Thr308 and Ser473. The most active compound (1a) has an IC50 6-fold lower than the Akt inhibitor, perifosine. These data suggest that the new compounds may be cytostatic and may have maximum clinical effects in NSCLC patients who do not respond to EGFR inhibitors. These findings prompt us to further explore the oxindole structure as leading scaffold to design new molecules with potent antitumor activity against NSCLC.

A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole-Fused Oxacycles

A unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides has been achieved in the presence of a chiral phase-transfer catalyst (PTC). This general strategy utilizes peroxides as unique bielectrophilic four- or five-atom synthons to participate in the C?C and the subsequent umpolung C?O bond-forming reactions with one-carbon unit nucleophiles, thus providing a distinct method to access the valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. DFT calculations were performed to rationalize the origin of high enantioselectivity. The gram-scale syntheses and synthetic utility of the resultant products were also demonstrated.

Design, synthesis and biological evaluation of 2-indolinone derivatives as PAK1 inhibitors in MDA-MB-231 cells

P21-activated kinase 1 (PAK1) plays a vital role in the proliferation, survival and migration of cancer cells, which has emerged as a promising drug target for cancer therapy. In this study, a series of 2-indolinone derivatives were designed and synthesized through a structure-based strategy. A potent PAK1 inhibitor (ZMF-005) was discovered, which presented an IC50 value of 0.22 μM against PAK1 with potent antiproliferative activity. Furthermore, we predicted the binding mode of ZMF-005 and PAK1 by molecule docking and dynamic (MD) simulation. In addition, ZMF-005 was documented to induce significant apoptosis and suppress migration in MDA-MB-231 cells. Collectively, these findings revealed that ZMF-005 is a novel potent PAK1 inhibitor for breast cancer treatment.

Indole-2-ketone derivative, preparation method and application thereof

The invention belongs to the field of medicines, particularly relates to an indole-2-ketone derivative, a preparation method and application thereof, and provides a compound represented by the following formula (I), a stereoisomer, a racemate, a tautomer,