33417-17-3

Usage

Uses

Used in Pharmaceutical Industry:
3-hydroxy-3-acetonyl-2-oxindole is used as an intermediate in the biosynthesis of HMG-CoA reductase inhibitors for the development of cholesterol-lowering drugs.
Used in Chemical Research:
3-hydroxy-3-acetonyl-2-oxindole is used as a key component in the synthesis of certain natural products, including antitumor agents, for the development of novel therapeutic agents.
Used in Anticancer Applications:
3-hydroxy-3-acetonyl-2-oxindole is studied for its potential anticancer properties, making it a promising candidate for the development of new cancer treatments.
Used in Antimicrobial Applications:
3-hydroxy-3-acetonyl-2-oxindole is studied for its potential antimicrobial properties, making it a candidate for the development of new antimicrobial agents.

InChI:InChI=1/C11H11NO3/c1-7(13)6-11(15)8-4-2-3-5-9(8)12-10(11)14/h2-5,15H,6H2,1H3,(H,12,14)

Upstream product

• 91-56-5 indole-2,3-dione 
• 109-89-7 diethylamine 
• 67-64-1 acetone 
• 700359-40-6 3-(2-oxopropyl)-3-tert-butyldimethylsilyl-oxyindolin-2-one 
• 220598-39-0 3-allyl-3-hydroxy-1,3-dihydro-2H-indol-2-one 
• 700359-39-3 3-allyl-3-tert-butyldimethylsilyloxyindolin-2-one 
• 541-50-4 2-acetoacetic acid 
• 109-77-3 malononitrile 
• 59-48-3 2-oxoindole 
• 1217-89-6 1-benzylisatin 

Downstream Products

• 76325-81-0 1,3-bis(3-hydroxy-3-oxindyl)-2-propanone 
• 634-38-8 2-methylquinoline-4-carboxylic acid 
• 91-56-5 indole-2,3-dione 
• 67-64-1 acetone 
• 3364-35-0 3-<2-Hydroxy-propyl>-indol 
• 500219-94-3 3-(2-hydroxypropyl)-3-hydroxy-2-oxindole 
• 79419-87-7 1-(4-Chloro-benzoyl)-3-imidazol-1-yl-3-(2-oxo-propyl)-1,3-dihydro-indol-2-one 
• 1383715-70-5 C₂₆H₂₁N₃O₃ 
• 1221577-88-3 (S)-3-hydroxy-3-((R)-2'-oxocyclohexyl)indolin-2-one 
• 1228658-39-6 (R)-3-hydroxy-3-((S)-2'-oxocyclohexyl)indolin-2-one 

Relevant academic research and scientific papers

Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone

Carane-derived β-amino alcohols with amino and hydroxy groups at positions 3 and 4 differing in their mutual arrangement and configuration were synthesized. Their application as organocatalysts in the asymmetric aldol reaction of isatin with acetone allowed one to obtain adducts with up to 84% enantiomeric excess.

Anti-inflammatory properties of convolutamydine A and two structural analogues

Aims: Convolutamydine A is an oxindole alkaloid that can be isolated from a marine bryozoan. Due to the variety of biological effects, two analogues were synthesized and their anti-inflammatory properties were evaluated. Main methods: The anti-inflammatory effects of convolutamydine A and its analogues (ISA003 and ISA147) were investigated in a formalin-induced licking behaviour model, where mice received an intraplantar injection of formalin and their licking behaviour was evaluated for 30 min. Additionally, inflammatory parameters were evaluated in a subcutaneous air pouch (SAP) model of carrageenan-induced inflammation. Exudates were collected for leukocyte counts; measurement of protein, prostaglandin E2 (PGE2) and cytokines by ELISA; and analysis of nitric oxide (NO) using a nitrate conversion protocol. Cyclooxygenase-2 (COX2) and inducible nitric oxide synthase (iNOS) from RAW 264.7 cells were quantified by immunoblotting. Key findings: Convolutamydine A and its two analogues inhibited the formalin-induced licking response at doses as low as 0.01 mg/kg. An inhibitory effect was also observed on leukocyte migration and the production of NO, PGE2 and cytokines (IL-6 and TNF-α). The reduction in inflammatory parameters did not appear to be correlated with a direct reduction in the number of cells in the SAP, because a reduction in NO and PGE2 production by cultured macrophages was observed in addition to the inhibition of iNOS and COX2 enzyme expression. Significance: These results indicate that convolutamydine A and its two analogues have significant anti-inflammatory effects. These substances can be improved to generate lead compounds for the synthesis of new anti-inflammatory drugs.

Convolutamydine A and synthetic analogues have antinociceptive properties in mice

Convolutamydine A, an oxindole that originated from a marine bryozoan, has several biological effects. In this study, we aimed to investigate the antinociceptive effects of convolutamydine A and two new synthetic analogues. Convolutamydine A and the two analogues were given orally to assess their ability to induce antinociceptive effects. Formalin-induced licking response, acetic acid-induced contortions, and hot plate models were used to characterize the effects of convolutamydine A and its analogues. Convolutamydine A (4,6-bromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole), compound 1 (3-(2-oxopropyl)-3-hydroxy-2-oxindole), and compound 2 (5-bromo-3-(2-oxopropyl)- 3-hydroxy-2-oxindole) caused peripheral antinociceptive and anti-inflammatory effects in the acetic acid-induced contortions and the formalin-induced licking models. Supraspinal effects were also observed in the hot plate model and were similar to those obtained with morphine. The peripheral effects were not mediated by the cholinergic or opioid systems. The antinociceptive effects of convolutamydine A seem to be mediated by all three systems (cholinergic, opioid, and nitric oxide systems), and the mechanism of action of compounds 1 and 2 involved cholinergic and nitric oxide-mediated mechanisms. Convolutamydine A and its analogues (compounds 1 and 2) showed good antinociceptive ability after systemic administration in acute pain models. The antinociceptive action mediated by cholinergic, opioid, and nitric oxide systems could explain why convolutamydine A, compound 1, and compound 2 retained their antinociceptive effects. The doses used were similar to the doses of morphine and were much lower than that of acetylsalicylic acid, the classical analgesic and anti-inflammatory drug. In conclusion, convolutamydine A and the two analogues demonstrated antinociceptive effects comparable to morphine's effects.

Copper(II) Triflate Catalyzed Regioselective and Enantioselective Propargylation of Isatin Derivatives by Using Allenylboronic Acid Pinacol Ester

We report a simple protocol for the synthesis of homopropargyl alcohols with isatin derivatives under milder conditions for the first time. The excellent regioselectivity and yields were observed with copper triflate as a Lewis-acid catalyst and allenylboronic acid pinacol ester as a nucleophile in aqueous media. A gram-scale synthesis was done to check the efficiency of the protocol with retention in selectivity. Further one-step functionalization of these homopropargyl alcohols was established as the synthetic application of these alkynes. The enantioselective synthesis of these chiral propargyl alcohols has also been explored for the first time with an enantiomeric ratio up to 12:88.

Control of Chemical Reactions by Using Molecules that Buffer Non-aqueous Solutions

Control of chemical reactions is necessary to obtain designer chemical transformation products and for preventing decomposition and isomerization reactions of compounds of interest. For the control of chemical events in aqueous solutions, the use of aqueo

Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols

Asymmetric aldol reactions of isatin and 4,6-dibromoisatin with acetone are efficiently catalyzed by β-amino alcohols derived from α-pinene and 3-carene. The target compounds can be isolated by crystallization from toluene, which eliminates the need for using chromatography and makes the asymmetric synthesis of (R)-convolutamydine A (up to 94% ee and yield 75%) simple and convenient.

Cu(II)-thiophene-2,5-bis(amino-alcohol) mediated asymmetric Aldol reaction and Domino Knoevenagel Michael cyclization: A new highly efficient Lewis acid catalyst

The highly efficient Lewis acid-catalytic system Cu(II)-thiophene-2,5-bis(amino-alcohol) has been developed for enantioselective Aldol reaction of isatin derivatives with ketones. The new catalytic system also proved to be highly enantioselective for the one pot three-component Domino Knoevenagel Michael cyclization reaction of substituted isatin with malononitrile and ethylacetoacetate. The chiral ligand (2S,20S)-2,20-((thiophene-2,5-diylbis(methylene))bis(azanediyl))bis(3-phenylpropan-1-ol) (L1) in combination with Cu(OAc)2Η2O employed as a new Lewis acid catalyst, furnished 3-substituted-3- hydroxyindolin-2-ones derivatives (3a-s) in good to excellent yields (81-99%) with high enantioselectivities (up to 96% ee) and spiro[4H-pyran-3,3-oxindole] derivatives (6a-l) in excellent yields (89-99%) with high ee (up to 95%). These aldol products and spiro-oxindoles constitute a core structural motif in a large number of pharmaceutically active molecules and natural products.

Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles

We developed an efficient acylative kinetic resolution of 3-hydroxy-3-substituted 2-oxindoles by a chiral DMAP derivative having a 1,1′-binaphthyl with two tert-alcohols units. A wide range of 3-hydroxy-3-substituted oxindoles having various functional groups were efficiently resolved (14 examples, up to s = 60) in the presence of 1 mol % of catalyst within 3-9 h. Multigram-scale reactions (10 g) also proceeded with a high s-factor (s = 43) within 5 h.

Oxidative ring expansion of 3-hydroxy-3-phenacyloxindoles using phenyliodine diacetate and molecular iodine: Synthesis of 2-hydroxy-2-aryl/alkyl-2,3-dihydroquinolin-4(1H)-ones

Oxidation of tertiary alcohol of the type 3-hydroxy-3-phenacyloxindoles using the combination of phenyliodine diacetate and molecular iodine in methanol results in oxidative cleavage of C2-C3 bond to form isocyanate as an intermediate with its subsequent

A Continuous-Flow Route to Enantioenriched 3-Substituted-3-Hydroxyoxindoles: Organocatalytic Aldol Reactions of Isatin with Acetone

An efficient L-leucinol catalysed asymmetric synthesis of 3-substitued-3-hydroxyoxindoles was for the first time completed under continuous flow, providing a safer route for accelerating the reaction at higher temperatures without adversely affecting enan