4290-91-9

Usage

Uses

Used in Pharmaceutical Industry:
1-BUTYL-1H-INDOLE-2,3-DIONE is used as a synthetic intermediate for the preparation of Spiro-epoxidized Indole-cyclopentenobutyrolactone compounds. These compounds have potential applications in the development of new pharmaceutical agents, particularly in the area of drug discovery and medicinal chemistry. The unique structural features of 1-BUTYL-1H-INDOLE-2,3-DIONE enable the creation of diverse and bioactive molecules, which can be further optimized for therapeutic efficacy and selectivity.

InChI:InChI=1/C12H13NO2/c1-2-3-8-13-10-7-5-4-6-9(10)11(14)12(13)15/h4-7H,2-3,8H2,1H3

Upstream product

• 109-65-9 1-bromo-butane 
• 91-56-5 indole-2,3-dione 
• 131543-46-9 Glyoxal 
• 1126-78-9 N-(n-butyl)aniline 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 62-53-3 aniline 
• 1249275-86-2 C₁₂H₁₉NO 
• 924-44-7 glyoxylic acid ethyl ester 
• 949511-22-2 2-(2-bromophenyl)-N-butylacetamide 
• 542-69-8 1-iodo-butane 
• 3486-31-5 isatin sodium salt 

Downstream Products

• 85044-87-7 1-Butyl-3-[(4,5-diphenyl-oxazol-2-yl)-hydrazono]-1,3-dihydro-indol-2-one 
• 1048973-62-1 N'-[(3Z)-1-(1-butyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]benzohydrazide 
• 1042156-45-5 C₁₉H₁₆F₃N₅O₅ 
• 503036-62-2 C₁₈H₁₈N₄O₃ 
• 502920-19-6 C₁₈H₁₇N₅O₅ 
• 112818-01-6 1-butyl-3-phenylindolin-2-one 

Relevant academic research and scientific papers

Structure and Isomerism of 2-(3-Substituted) Quinoxalinylhydrazones of Isatin and Its Homologs

Mono- and dihydrazones, the structure of which were established by means of 1H and 13C NMR, IR, and electronic absorption spectroscopy, were synthesized by reaction of 3-chloro-2-hydrazino- and 2,3-dihydrazinoquinoxalines with 1H-indole-2,3-dione and its 1-methyl and 1-butyl homologs.Thermal and photochemical conversion of the E, Z isomer to the Z isomer is observed, while the reverse transformation is observed in the case of treatment with alkali.

Selective "naked eye" detection of Al(iii) and PPi in aqueous media on a rhodamine-isatin hybrid moiety

A highly selective fluorescence probe, RIH (rhodamine-isatin hybrid) for Al3+ has been designed and synthesized. This new dual signal (colorimetric and fluorogenic "off-on" type) chemosensing ensemble based on the complex between RIH and Al3+ has also been effective to selectively discriminate PPi from other anions in aqueous solution at physiological pH. The Royal Society of Chemistry 2013.

Thiophene-functionalized octupolar triindoles: Synthesis and photophysical properties

Two thiophene-functionalized octupolar triindole molecules were synthesized through Suzuki and Sonogashira cross-coupling reactions. Their photophysical and electrochemical properties were explored. The spectroscopic data demonstrate that triindole is an

Rongalite-induced transition-metal and hydride-free reductive aldol reaction: a rapid access to 3,3′-disubstituted oxindoles and its mechanistic studies

A transition-metal and hydride-free reductive aldol reaction has been developed for the synthesis of biologically active 3,3′-disubstituted oxindoles from isatin derivatives using rongalite. In this protocol, rongalite plays a dual role as a hydride-free

Fluorine-substituted indolo-thiadiazoloquinoxaline-based D-A type polymers for photovoltaic applications

Two D-A type conjugated polymers, in which the electron-donating benzodithiophene monomers are connected to the electron-accepting indolo-thiadiazoloquinoxaline (ITQ) monomers via a thiophene bridge, are synthesized under Stille coupling conditions. Once the reference PB-ITQ is prepared, one fluorine atom is incorporated into the ITQ unit of PB-ITQ to afford the additional target polymer PB-ITQF. An inverted-type device with the configuration of indium tin oxide (ITO)/ZnO/Polymer:PC71BM/MoO3/Ag is utilized to examine the photovoltaic properties of the two polymers. Owing to the positive contributions of fluorine atoms, all the photovoltaic parameters of the device based on PB-ITQF such as the short-circuit current density, open-circuit voltage, and fill factor are improved as compared with those of the device based on PB-ITQ. As a result, the highest PCE of 2.32% is achieved from the fullerene-based polymer solar cell based on PB-ITQF.

Isatin-linked 4,4-dimethyl-5-methylene-4,5-dihydrothiazole-2-thiols for inhibition of acetylcholinesterase

A series of novel isatin-linked 4,4-dimethyl-5-methylene-4,5-dihydrothiazole-2-thiols (IT2Ts) 1a–1g were designed as acetylcholinesterase (AChE) inhibitors capable of interacting with both the catalytic active site (CAS) and peripheral anionic site (PAS) of the enzyme simultaneously. The target IT2Ts were prepared through a short synthesis in moderate yield. The most potent inhibitors of this series 1b and 1c (IC50 = 18.2 and 27.5 μM, respectively) outperformed rivastigmine and were comparable to galantamine, both clinically used AChE inhibitors. Furthermore, 1b displayed non-competitive inhibition patterns in kinetic studies, whereas molecular modeling predicted a simultaneous interaction with both the CAS and PAS. In silico methods predicted several promising drug-like characteristics of 1b. Taken together, these results indicate 1b warrants further investigation as a multitarget-directed ligand for AChE inhibition. [Figure not available: see fulltext.]

Palladium-Catalyzed Cascade Hydrosilylation and Amino-Methylation of Isatin Derivatives

We demonstrate that using palladium acetate as a catalyst for reduction of DMF and isatin derivatives by hydrosilanes, a cascade hydrosilylation and amino-methylation reaction can be realized. With DMF as a reactant and a solvent, the in-situ generated siloxymethylamine intermediate, an adduct of DMF and hydrosilanes, smoothly participates in the successive stages, providing a serials of Si, N-functionalized indolin-2-ones in moderate to good yields. This strategy exhibits high chemoselectivity toward carbonyl moieties reduction among the substrates. (Figure presented.).

Acylation of oxindoles using methyl/phenyl estersviathe mixed Claisen condensation - an access to 3-alkylideneoxindoles

Predominantly, aggressive acid chlorides and stoichiometric coupling reagents are employed in the acylating process for synthesizing carbonyl tethered heterocycles. Herein, we report simple acyl sources,viz. methyl and phenyl esters, which acylate oxindolesviathe mixed Claisen condensation. This straightforward protocol is mediated by LiHMDS and KOtBu and successfully applied to a wide range of substrates. It is a noteworthy transformation that skips the stepwise generation of enolates and acylation, and the reaction is performed at a moderate temperature with no side reactions. This protocol produces the first examples ofortho-substituents in an aryl ring flanked with electron-donating and electron-withdrawing substrates. Interestingly, robust organometallic ferrocenyl methyl ester cleaved under these conditions with ease. Furthermore, biologically important Tenidap's analog was synthesized by this protocol.

Novel Multitarget Directed Triazinoindole Derivatives as Anti-Alzheimer Agents

The multifaceted nature of Alzheimer's disease (AD) demands treatment with multitarget-directed ligands (MTDLs) to confront the key pathological aberrations. A novel series of triazinoindole derivatives were designed and synthesized. In vitro studies revealed that all the compounds showed moderate to good anticholinesterase activity; the most active compound 23e showed an IC50 value of 0.56 ± 0.02 μM for AChE and an IC50 value of 1.17 ± 0.09 μM for BuChE. These derivatives are also endowed with potent antioxidant activity. To understand the plausible binding mode of the compound 23e, molecular docking studies and molecular dynamics simulation studies were performed, and the results indicated significant interactions of 23e within the active sites of AChE as well as BuChE. Compound 23e successfully diminished H2O2-induced oxidative stress in SH-SY5Y cells and displayed excellent neuroprotective activity against H2O2 as well as Aβ-induced toxicity in SH-SY5Y cells in a concentration dependent manner. Furthermore, it did not show any significant toxicity in neuronal SH-SY5Y cells in the cytotoxicity assay. Compound 23e did not show any acute toxicity in rats at doses up to 2000 mg/kg, and it significantly reversed scopolamine-induced memory deficit in mice model. Additionally, compound 23e showed notable in silico ADMET properties. Taken collectively, these findings project compound 23e as a potential balanced MTDL in the evolution process of novel anti-AD drugs.

Synthesis of isatin based N1-alkylated 3-β-C-glycoconjugated-oxopropylidene oxindoles as potent antiplasmodial agents

In an attempt to develop new antimalarial drugs, we have synthesized a new class of N-alkylated 3-glycoconjugated-oxopropylidene oxindoles starting from substituted isatins and glucopyranosyl propanone via a well-known cross-aldol reaction followed by deh