1861-29-6

Usage

InChI:InChI=1/C9H7NO/c1-6-7-4-2-3-5-8(7)10-9(6)11/h2-5H,1H2,(H,10,11)

Upstream product

• 87-51-4 indole-3-acetic acid 
• 292851-35-5 3-acetoxy-1-acetyl-3-methylindolin-2-one 
• 154867-50-2 N-(2-iodophenyl)propiolamide 
• 59-48-3 2-oxoindole 
• 50-00-0 formaldehyd 
• 91-56-5 indole-2,3-dione 
• 19493-09-5 Methylenetriphenylphosphorane 
• 16990-74-2 3-hydroxy-3-methyloxindole 
• 615-43-0 2-iodophenylamine 
• 292851-37-7 3-methoxycarbonyloxy-3-methylindolin-2-one 
• 68543-20-4 3-acetoxy-3-methylindolin-2-one 

Downstream Products

• 18747-95-0 1-methyl-2-piperidinecarbonitrile 
• 1352401-92-3 methyl (2'S,3R,5'S)-1'-acetyl-2-oxo-2'-[4-(trifluoromethyl)phenyl]-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylate 
• 1352401-91-2 methyl (2'S,3R,5'S)-1'-acetyl-2'-(4-cyanophenyl)-2-oxo-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylate 
• 1352401-90-1 methyl (2'R,3R,5'S)-1'-acetyl-2'-(2,3-dichlorophenyl)-2-oxo-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylate 
• 1352401-89-8 methyl (2'R,3R,5'S)-1'-acetyl-2'-(2-bromo-3-hydroxy-4-methoxyphenyl)-2-oxo-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylate 
• 1352401-88-7 methyl (2'S,3R,5'S)-1'-acetyl-2'-(4-methoxyphenyl)-2-oxo-1,2-dihydrospiro[indole-3,3'-pyrrolidine]-5'-carboxylate 

Relevant academic research and scientific papers

A kinetic and mechanistic study on the oxidation of indole-3-acetic acid by peroxodisulfate

The kinetics of oxidation of indole-3-acetic acid (IAA) by peroxodisulfate (PDS) has been carried out in aqueous acetic acid medium. First-order dependence of rate each with respect to (IAA] and [PDS) was observed. The reaction rate was unaffected by added [H+]. Increase of percentage of acetic acid decreased the rate. Variation of ionic strength (μ) had negligible influence on the rate. A suitable kinetic scheme based on these observations involving a nonradical mechanism is proposed. The reactivity of peroxodisulfate toward indole-3-acetic acid was found to be lower than that with peroxomonosulfate.

Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare

In our continued efforts to improve the potential utility of the α-methylene-γ-lactone scaffold, 62 new and 59 known natural α-methylenelactam analogues including α-methylene-γ-lactams, α-arylidene-γ and δ-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the α-methylenelactone scaffold. The results of antifungal and cytotoxic activity indicated that among these derivatives compound (E)-1-(2, 6-dichlorobenzyl)-3-(2-fluorobenzylidene) pyrrolidin-2-one (Py51) possessed good selectivity with the highest antifungal activity against Colletotrichum orbiculare with IC50?=?10.4?μM but less cytotoxic activity with IC50?=?141.2?μM (against HepG2 cell line) and 161.2?μM (against human hepatic L02?cell line). Ultrastructural change studies performed by transmission electron microscope showed that Py51 could cause important cell morphological changes in C.?orbiculare, such as plasma membrane detached from cell wall, cell wall thickening, mitochondria disruption, a dramatic increase in vacuolation, and eventually a complete loss in the integrity of organelles. Significantly, mitochondria appeared one of the primary targets, as confirmed by their remarkably aberrant morphological changes. Analysis of structure–activity relationships revealed that incorporation of the aryl group into the α-exo-methylene and the N-benzyl substitution increased the activity. Meanwhile, the α-arylidene-γ-lactams have superiority in selectivity over the 3-arylideneindolin-2-ones. Based on the results, the N-benzyl substituted α-(2-fluorophenyl)-γ-lactam was identified as the most promising natural-based scaffold for further discovering and developing improved crop-protection agents.

Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast

3-Substituted oxindoles are very interesting molecules both for their potential biological activity and for their role as starting materials toward more complex oxindole-based structures. These molecules can be prepared by the reduction of a 3-ylidene oxi

Construction of 1-pyrroline skeletons by Lewis acid-mediated conjugate addition of vinyl azides

Lewis acid-mediated conjugate addition of vinyl azides to electron-deficient alkenes led to the efficient construction of 1-pyrroline skeletons. The reactions of vinyl azides with 3-alkylidene-2-oxoindolines afford 3′,4′-dihydrospiro[indoline-3,2′-pyrrol]-2-ones in a diastereoselective fashion, whereas those with dimethyl 2-alkylidenemalonates provide 4,5-dihydro-3H-pyrroles.

Phosphine-catalyzed enantioselective γ-addition of 3-substituted oxindoles to 2,3-butadienoates and 2-butynoates: Use of prochiral nucleophiles

The first phosphine-catalyzed enantioselective γ-addition with prochiral nucleophiles and 2,3-butadienoates as the reaction partners has been developed. Both 3-alkyl- and 3-aryl-substituted oxindoles could be employed in this process, which is catalyzed by a chiral phosphine that is derived from an amino acid, thus affording oxindoles that bear an all-carbon quaternary center at the 3-position in high yields and excellent enantioselectivity. The synthetic value of these γ-addition products was demonstrated by the formal total synthesis of two natural products and by the preparation of biologically relevant molecules and structural scaffolds.

Alantrypinone and its derivatives: Synthesis and antagonist activity toward insect GABA receptors

The γ-aminobutyric acid (GABA) receptor bears important sites of action for insecticides. Alantrypinone is an insecticidal alkaloid that acts as a selective antagonist for housefly (vs rat) GABA receptors, and is considered to be a lead compound for the d

Synthesis of functionalized spiroaziridine-oxindoles from 3-ylideneoxindoles: an easy route to 3-(aminoalkyl)oxindoles

Novel potentially bioactive spiroaziridine-oxindoles have been prepared by treatment of easily accessible 3-ylidene-oxindoles with N-{[(4-nitrophenyl) sulfonyl]oxy}carbamate (NsONHCO2Et) in the presence of CaO. These compounds gave new 3-(amino

Stereoselective synthesis of 3-alkylideneoxindoles using tandem indium-mediated carbometallation and palladium-catalyzed cross-coupling reactions

The first efficient methods for the stereoselective synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles via radical cyclization reactions were investigated using tandem indium-mediated carbometallation and palladium-catalyzed cross-co

Reactivity toward thiols and cytotoxicity of 3-methylene-2-oxindoles, cytotoxins from indole-3-acetic acids, on activation by peroxidases

Oxidation of indole-3-acetic acid and its derivatives by peroxidases such as that from horseradish produces many products, including 3-methylene-2-oxindoles. These have long been associated with biological activity, but their reactivity has not been characterized. We have previously demonstrated the potential value of substituted indole acetic acids and horseradish peroxidase as the basis for targeted cancer therapy, since the compounds are of low cytotoxicity until oxidized, when high cytotoxicity is observed; the combination of prodrug and enzyme depletes intracellular thiols. In this study, 3-methylene-2-oxindole and derivatives substituted in the 4-, 5-, or 6-position with methyl, F, or Cl have been synthesized and their reactivity toward representative thiol nucleophiles (glutathione, cysteine, and a cysteinyl peptide) measured using stopped-flow kinetic spectrophotometry. Rate constants were in the range ～2 × 103 to 2 × 104 M-1 s-1 at pH 7.4, 25°C, implying a lifetime of a few tens of milliseconds for these methylene oxindoles in the cellular environment and diffusion distances of a few micrometers. As expected, halogen substitution decreased the rate of production of the methylene oxindoles on treatment of horseradish peroxidase. The cytotoxicities of the compounds were measured using Chinese hamster V79 fibroblast-like cells in vitro. The halogen-substituted derivatives were much more cytotoxic than the 5-methyl analogue or the parent (unsubstituted) compound, consistent with the trends in rate constant for reaction with the thiols. The results show that the cytotoxic response in the prodrug (indole acetic acid) and enzyme (horseradish peroxidase) system reflects the reactivity of methylene oxindoles toward nucleophiles much more than the rate of generation of the oxindoles, and helps explain the possible advantages of 5-fluoroindole-3 -acetic acid compared to IAA as a lead compound for investigation in targeted cancer therapy.

A convenient synthesis of 3-methyleneoxindoles: Cytotoxic metabolites of indole-3-acetic acids

3-Methyleneoxindole is a cytotoxic metabolite of indole-3-acetic acid with potential for use in cancer therapy. This species and ring-substituted analogues are conveniently synthesised from the corresponding isatins via a Peterson olefination.