6623-89-8

Usage

Uses

Used in Organic Synthesis:
(2-oxo-1,2-dihydro-3H-indol-3-ylidene)propanedinitrile is used as a building block for the synthesis of various heterocyclic compounds and pharmaceuticals. Its reactive imine group allows for the formation of new chemical bonds and the creation of diverse molecular structures.
Used in Pharmaceutical Development:
(2-oxo-1,2-dihydro-3H-indol-3-ylidene)propanedinitrile is used as a key intermediate in the development of new pharmaceuticals. Its potential biological activities, such as antiviral, anticancer, and anti-inflammatory properties, make it a promising candidate for the treatment of various diseases and conditions.
Used in Research:
(2-oxo-1,2-dihydro-3H-indol-3-ylidene)propanedinitrile is used as a research compound to explore its chemical properties and potential applications. Its versatility and significance in organic chemistry make it an important tool for understanding the behavior of similar compounds and developing new synthetic methods and techniques.

Upstream product

• 109-77-3 malononitrile 
• 193686-70-3 2-nitroindole 
• 22105-09-5 4‐hydroxycoumarin 
• 91-56-5 indole-2,3-dione 
• 6011-63-8 3-hydroxy-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione 
• 59-48-3 2-oxoindole 
• 61-71-2 dioxindol 
• 13504-73-9 triphenylphosphoranylidene-malononitrile 
• 126326-47-4 dimethyl phosphonate 

Downstream Products

• 75460-01-4 spiro 
• 75460-01-4 spiro 
• 1022193-64-1 2-(4-bromophenyl)-N'-(2H-thiazolo[5,4-b]indol-2-ylidene)acetohydrazide 
• 1022193-68-5 2-(4-bromophenyl)-N'-(3-cyanopyrrolo[2,3-b]indol-2(1H)-ylidene)acetohydrazide 
• 1022193-62-9 N'-(2H-thiazolo[5,4-b]indol-2-ylidene)benzohydrazide 
• 1022193-66-3 N'-(3-cyanopyrrolo[2,3-b]indol-2(1H)-ylidene)benzohydrazide 
• 1022193-63-0 4-hydroxy-N'-(2H-thiazolo[5,4-b]indol-2-ylidene)benzohydrazide 
• 1022193-67-4 N'-(3-cyanopyrrolo[2,3-b]indol-2(1H)-ylidene)-4-hydroxybenzohydrazide 
• 1138324-72-7 5-amino-3-benzyl-6-cyano-2,2-diphenylpyrano[2,3-d]thiazolidine-7-spiro-3'-(indolin-2'-one) 
• 1158568-59-2 C₂₆H₂₄N₄O₂S 
• 1158568-52-5 C₂₅H₂₂N₄O₂S 
• 1123744-15-9 5-amino-2-oxo-1-(4'-methoxyphenyl)-1,1',2',3a,7,7a'-hexahydrospiro[indole-3',7-pyrano[3,2-b]pyrrole]-3,6'-dicarbonitrile 
• 1123744-16-0 5-amino-2-oxo-1-(4'-methylphenyl)-1,1',2',3a,7,7a'-hexahydrospiro[indole-3',7-pyrano[3,2-b]pyrrole]-3,6'-dicarbonitrile 
• 1213236-23-7 C₂₂H₁₃N₅O 

Relevant academic research and scientific papers

Imino isatin derivatives; synthesis, in silico molecular dynamic study over monoamine oxidase B, ADME prediction, and in vitro cytotoxicity evaluation

The monoamine oxidase B (MAO-B) depicts an attractive drug target for the development of neuro protective agents toward the treatment of neurodegenerative diseases. The current study involved synthesis, in silico and cytotoxic evaluation of N1-alkylated-5-substituted 3-imino isatin derivatives with the proposed MAO-B inhibitory activities. The In silico molecular modeling investigation was performed through the induced fit docking, molecular mechanics-generalized born surface area, and molecular dynamic method in order to uncover the binding mode interaction and their proposed impact on the active site environment and flexibility. The synthesized compounds were characterized by spectroscopic methods. Compound 3-Imino-1-pentyl indolin-2-one (3h) with the highest free binding energy adopts an extended conformation spanning from the flavin ring location to the entrance of the substrate cavity. In this way, Ile199 adopts the “open” conformation so the two separate cavities of MAO-B active site fused and formed a single-space, which abled the compound extending to the MAO-B entrance cavity space. From consideration of the data presented in this paper, we reveal that longer N1-alkylated-3-imino isatin derivative could be proposed as inhibitor that would occupy both cavities of the MAO-B active site. Furthermore, the mentioned derivatives provided acceptable drug profiling based on in silico ADME calculation and MTT cytotoxicity test evaluation.

Nukleophile Reaktionen an 2-Phenylindolenin-3-onen

Nucleophilic reagents such as 4-nitrophenylhydrazine, malonic acid derivatives, and hydrogen peroxide react with 2-phenylindolenin-3-ones giving, in the first step, addition products to the N=C(2) bond.This addition can be reversible, but in most cases ne

An efficient procedure for the synthesis of spiro [3H-indole-3,4' (1'H) pyrano [2,3-C] pyrrole]-5'-carbonitriles using solid inorganic supports and microwave activation

Microwave irradiation accelerates the Michael condensation of 3- dicyanomethylene-2H-indole-2-one with 2-pyrrolidone/N-methyl-2-pyrrolidone (i) adsorbed on neutral alumina in 'dry media' (ii) using absolute ethanol as energy transfer medium. 3-Dicyanomethylene-2H-indol-2-one was synthesized under microwave irradiation using indole-2,3-dione and malononitrile. The results were compared with those obtained following the classical method. The advantages obtained by the use of microwave irradiation are demonstrated.

An environmentally benign approach for the synthesis of 3,3′-pyrrolidonyl spirooxindole derivatives via a cascade Knoevenagel-Michael-cyclization multicomponent reaction

A series of 3,3′-pyrrolidonyl spirooxindole derivatives have been synthesized in good yields from the cascade Knoevenagel-Michael-cyclization multicomponent reaction of isatin, malononitrile and α-isothiocyanato imide in the presence of a catalytic amount

Facile microwave-assisted one-pot solid phase synthesis of spiro[3H-indole-3,4′-pyrazolo[3,4-b] pyridines]

A rapid, enviro-economic protocol for the novel one-pot synthesis of a series spiro [3H-indole-3,4′-pyrazolo[3,4-b]pyridines (7a-f) under microwave irradiation is described. The intermediates spiro pyrazolopyran (5) and dicyanomethylene indole-2-one (3) w

Synthesis of novel 2-oxospiro[indoline-3,4′-[1,3]dithiine]-5′-carbonitrile derivatives by new spiro[indoline-3,4′-[1,3]dithiine]?Cu(NO3)2 supported on Fe3O4?gly?CE MNPs as efficient catalyst and evaluation of biological activity

New spiro[indoline-3,4′-[1,3]dithiine]?Cu(NO3)2 supported on Fe3O4?gly?CE magnetic nanoparticle were synthesized and used as efficient and recyclable catalyst in the synthesis of 2-oxospiro[indoline-3,4′-[1,3]dithiine]-5′-carbonitrile derivatives. The structure of magnetic nanoparticles were confirmed using energy-dispersive X-ray spectroscopy (EDX), X-ray diffraction (XRD), scanning electron microscopy (SEM), vibrating sample magnetometer (VSM), thermogravimetric analysis (TGA), infrared spectroscopy (FT-IR) and inductively coupled plasma optical emission spectroscopy (ICP-OES). Subsequently, antibacterial and antifungal activities in terms of inhibition zone diameter, minimum inhibitory concentration, minimum bactericidal concentration and antioxidant activity against the DPPH free radical of the derivatives were investigated. The results revealed acceptable biological effects of the synthetic derivatives and a significant relationship between their structure and biological activity were observed.

Regio- and stereoselective synthesis of novel dispiropyrrolidine: Bisoxindole derivatives via multicomponent reactions

A convenient and efficient method for the synthesis of novel dispiropyrrolidine bisoxindole derivatives by 1,3-dipolar cycloaddition reaction of azomethine ylides has been developed. The synthesis was achieved by using a one-pot multicomponent procedure. The features of this procedure were characterized by the following: mild reaction conditions, high yields, high regio- and stereoselectivity, one-pot procedure, and operational simplicity.

Four-Component Reaction Access to Nitrile-Substituted All-Carbon Quaternary Centers

A four-component reaction strategy for access to acyclic nitrile-substituted all-carbon quaternary centers is disclosed. In the presence of a DABCO-based ionic liquid catalyst, the reactions proceed smoothly with a wide range of substrates efficiently to deliver nitrile-substituted all-carbon quaternary centers under mild reaction conditions. This protocol is further demonstrated as an efficient method for the construction of contiguous all-carbon quaternary centers. All the reactions are easily operated in a green manner, producing water as the only byproduct. Some of the products show excellent activity against specific fungi.

A Simplistic Approach for Preparation of Alkylidenemalononitrile Derivatives: Characterization, In silico Studies, Quantum Chemical Evaluation, Molecular Docking, and In vitro Biological Activity Evaluation

A new and efficient green grinding-based catalyst free Knoevenagel condensation of aldehydes/ketones and malononitrile for the rapid preparation of twelve malononitrile derivatives (C1-C12) is proposed. Characterization of the derivatives was done by sup

Site-specific role of bifunctional graphitic carbon nitride catalyst for the sustainable synthesis of 3,3-spirocyclic oxindoles in aqueous media

Functionalized graphitic carbon nitride (Sg-C3N4) has been manufactured and used as a reusable catalyst for the one-pot production of various spiro-pyrano chromenes and spiro indole-3,1′-naphthalene tetracyclic systems in aqueous med