3265-23-4

Basic information

• Product Name: 3-HYDRAZONO-1-METHYL-1,3-DIHYDRO-INDOL-2-ONE
• Synonyms: 1H-Indole-2,3-dione,1-Methyl-, 3-hydrazone
• CAS NO: 3265-23-4
• Molecular Formula: C₉H₉N₃O
• Molecular Weight: 175.19
• Mol File: 3265-23-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 104-106 °C
• Boiling Point: 342.9°Cat760mmHg
• Flash Point: 161.2°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 7.29E-05mmHg at 25°C
• Refractive Index: 1.675
• PKA: -2.17±0.20(Predicted)
• CAS DataBase Reference: 3-HYDRAZONO-1-METHYL-1,3-DIHYDRO-INDOL-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDRAZONO-1-METHYL-1,3-DIHYDRO-INDOL-2-ONE(3265-23-4)
• EPA Substance Registry System: 3-HYDRAZONO-1-METHYL-1,3-DIHYDRO-INDOL-2-ONE(3265-23-4)

Safety Data

• Hazardous Substances Data: 3265-23-4(Hazardous Substances Data)

Usage

Description

3-HYDRAZONO-1-METHYL-1,3-DIHYDRO-INDOL-2-ONE is a heterocyclic chemical compound characterized by an indole backbone and a hydrazono functional group. With the molecular formula C9H10N2O, this compound possesses diverse biological activities, such as anti-inflammatory and anti-cancer properties, making it a promising candidate for pharmaceutical and medicinal chemistry applications.
Used in Pharmaceutical Industry:
3-HYDRAZONO-1-METHYL-1,3-DIHYDRO-INDOL-2-ONE is used as a pharmaceutical agent for its potential anti-inflammatory and anti-cancer properties. Its unique structure and reactivity contribute to its value in drug discovery and development, with ongoing research aimed at exploring its properties and potential applications for future therapeutic interventions.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3-HYDRAZONO-1-METHYL-1,3-DIHYDRO-INDOL-2-ONE serves as a valuable tool for the development of new drugs. Its diverse biological activities and unique chemical structure make it an attractive candidate for designing and synthesizing novel therapeutic agents targeting various diseases and conditions.

InChI:InChI=1/C9H9N3O/c1-12-7-5-3-2-4-6(7)8(11-10)9(12)13/h2-5H,10H2,1H3/b11-8+

Upstream product

• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 91-56-5 indole-2,3-dione 
• 3265-14-3 3-diazo-1-methyl-1,3-dihydro-indol-2-one 

Downstream Products

• 1139780-27-0 C₁₇H₁₄N₄O₂S 

Relevant articles and documents

Electrochemical synthesis of a 6-coordinate cadmium(II) complex with N-methylisatin N(4)-cyclohexylthiosemicarbazone

Cadmium metal was oxidized in the presence of N-methylisatin N(4)-cyclohexyl-thiosemicarbazone (HMeIs4Chex) in an acetonitrile solution, which produced a complex of the formula [Cd(MeIs4Chex)2]. The two MeIs4Chex ligands are at an angle close to 90° from each other, and there is hydrogen bonding to two adjacent molecules by the anionic ligands remaining NH groups. The complex crystallizes in the monoclinic space group P21/c with a = 11.820(4), b = 11.491(4), c = 27.834(4) A, β = 106.82(2)°, V = 3618.7(17) A°3 and Z = 4.

Squaramide-catalyzed asymmetric Mannich reactions between 3-fluorooxindoles and pyrazolinone ketimines

An enantioselective Mannich reaction between 3-fluorooxindoles and pyrazolinone ketimines has been developed for the construction of amino-pyrazolone-oxindoles containing stereogenic C-F units. Based on this new protocol that allows for the generation of two adjacent tetrasubstituted stereocenters, a variety of structurally diverse fluorinated amino-pyrazolone-oxindoles were obtained in good to excellent yields with excellent diastereoselectivities and enantioselectivities (up to 98% yield, >20:1 dr and >99% ee). What's more, good yield and high stereoselectivities were obtained in the gram-scale reaction.

Novel [(3-indolylmethylene)hydrazono]indolin-2-ones as apoptotic anti-proliferative agents: design, synthesis and in vitro biological evaluation

On account of their significance as apoptosis inducing agents, merging indole and 3-hydrazinoindolin-2-one scaffolds is a logic tactic for designing pro-apoptotic agents. Consequently, 27 hybrids (6a–r, 9a–f and 11a–c) were synthesised and evaluated for their cytotoxicity against MCF-7, HepG-2 and HCT-116 cancer cell lines. SAR studies unravelled that N-propylindole derivatives were the most active compounds such as 6n (MCF-7; IC50=1.04 μM), which displayed a significant decrease of cell population in the G2/M phase and significant increase in the early and late apoptosis by 19-folds in Annexin-V-FTIC assay. Also, 6n increased the expression of caspase-3, caspase-9, cytochrome C and Bax and decreased the expression of Bcl-2. Moreover, compounds 6i, 6j, 6n and 6q generated ROS by significant increase in the level of SOD and depletion of the levels of CAT and GSH-Px in MCF-7.