41192-31-8

Usage

Derivative of oxindole

A heterocyclic compound with a five-membered ring containing oxygen, nitrogen, and carbon atoms 1-Methyl-5-fluorooxindole is derived from oxindole by modifying its structure.

Unique properties

The addition of a methyl group and a fluorine atom These structural modifications give 1-Methyl-5-fluorooxindole its distinct properties compared to its parent compound, oxindole.

Potential applications

Pharmaceutical research This chemical compound may be useful in the development of new drugs due to its unique properties and structural features.

Building block for synthesis

Other organic compounds 1-Methyl-5-fluorooxindole can be used as an intermediate in the synthesis of other organic compounds, making it a valuable component in organic chemistry.

Valuable tool

Studies related to organic chemistry and medicinal chemistry The structural characteristics of 1-Methyl-5-fluorooxindole make it an important compound for research in these fields, potentially leading to new discoveries and advancements.

Upstream product

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Downstream Products

• 773-91-1 5-fluoro-1-methylisatin 
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Relevant academic research and scientific papers

CONJUGATES OF AMPK INHIBITORS AND PROTAC DEGRADERS AND RELATED USES

The present disclosure relates to compounds of Formula (I): T-L-D, stereoisomers thereof, prodrugs thereof, and pharmaceutically acceptable salts thereof, wherein T is an AMPK inhibiting moiety; L is a linking moiety; and D is a PROTAC degrading moiety. The present disclosure also relates to uses of the compounds, e.g., to inhibit AMP-Activated protein kinase (AMPK), degrading AMPK protein, and/or treat cancer in a subject.

Heterogeneous palladium-catalysed intramolecular C(sp3)[sbnd]H α-arylation for the green synthesis of oxindoles

Herein, we present our results on the development of a waste-minimized protocol for the synthesis of oxindoles using cyclopentyl methyl ether (CPME) as a safe and green reaction medium and palladium on carbon (Pd/C) as a reusable catalyst. This protocol is efficiently applied to a variety of substrates affording products with excellent yields, minimal metal contamination and minimum waste production. The catalyst was recovered and reused for four consecutive runs without any apparent loss of efficiency. Moreover, products were isolated by simple precipitation from heptane with no need for chromatographic separations, and both CPME and heptane were recovered. Waste-minimization is reflected by the low E-factor calculated for the presented protocol.

AMP-ACTIVATED PROTEIN KINASE INHIBITORS AND METHODS OF MAKING AND USING THE SAME

The present disclosure relates to compounds of Formula (I): (I); stereoisomers thereof, prodrugs thereof, and pharmaceutically acceptable salts thereof. The present disclosure also relates to uses of the compounds, e.g., to inhibit AMP-Activated protein kinase (AMPK) and treat cancer in a subject.

Substituted oxindol-3-ylidenes as AMP-activated protein kinase (AMPK) inhibitors

AMP-activated protein kinase (AMPK) is a central metabolic regulator that promotes cancer growth and survival under hypoxia and plays a role in the maintenance of cancer stem cells. A major challenge to interrogating the potential of targeting AMPK in cancer is the lack of potent and selective small molecule inhibitors. Compound C has been widely used as an AMPK inhibitor, but it lacks potency and has a poor selectivity profile. The multi-kinase inhibitor, sunitinib, has demonstrated potent nanomolar inhibition of AMPK activity and has scope for modification. Here, we have designed and synthesized several series of oxindoles to determine the structural requirements for AMPK inhibition and to improve selectivity. We identified two potent, novel oxindole-based AMPK inhibitors that were designed to interact with the DFG motif in the ATP-binding site of AMPK, this key feature evades interaction with the common recptor tyrosine kinase targets of sunitinib. Cellular engagement of AMPK by these oxindoles was confirmed by the inhibition of phosphorylation of acetyl-CoA carboxylase (ACC), a known substrate of AMPK, in myeloid leukemia cells. Interestingly, although AMPK is highly expressed and activated in K562 cells these oxindole-based AMPK inhibitors did not impact cell viability or result in significant cytotoxicity. Our studies serve as a platform for the further development of oxindole-based AMPK inhibitors with therapeutic potential.

Annulation reaction of cyclic pyridinium ylides with: In situ generated azoalkenes for the construction of spirocyclic skeletons

Two new types of cyclic pyridinium ylides were designed and further used in reactions with azoalkenes to access structurally diverse spirocyclic compounds. A range of spiropyrazoline oxindoles could be smoothly obtained in up to 99% yield via a [4 + 1] annulation process with oxindole 3-pyridinium ylides as C1 synthons. Similarly, a series of spiropyrazoline indanones could be prepared with indanone 2-pyridinium ylides as C1 synthons. This work represents the first example of cyclic pyridinium ylides as C1 synthons for the efficient construction of spirocyclic compounds.

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.

Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles

Rationally designed fluorene-based mono- and bimetallic Pd-PEPPSI complexes were synthesized and demonstrated to be effective for the one-pot sequential α-arylation/alkylation of oxindoles. This streamlined approach offers efficient access to functionalized 3,3-disubstituted oxindoles in excellent yields (up to 89%) under mild reaction conditions.

Cinchona-alkaloid-catalyzed enantioselective hydroxymethylation of 3-fluorooxindoles with paraformaldehyde

Cinchona-alkaloid-catalyzed hydroxymethylation of 3-fluorooxindoles using paraformaldehyde as the C1 unit was achieved. A wide range of 3-fluorooxindoles was successfully reacted to give the corresponding 3-fluoro-3-hydroxymethyloxindoles with high efficiency and moderate to good enantioselectivity.

Palladium-catalyzed carbonylative α-arylation of 2-oxindoles with (Hetero)aryl bromides: Efficient and complementary approach to 3-acyl-2-oxindoles

An efficient Pd-catalyzed carbonylative α-arylation of 2-oxindoles with aryl and heteroaryl bromides for the one-step synthesis of 3-acyl-2-oxindoles has been developed. This reaction proceeds efficiently under mild conditions and is complementary to the

Palladium-catalyzed amidation by chemoselective C(sp3)-H activation: Concise route to oxindoles using a carbamoyl chloride precursor

Quite select: A new strategy was developed for the synthesis of various oxindoles from carbamoyl chlorides. Under the optimum reaction conditions, with Ad2PBu as a ligand, tBuCONHOH as an additive, and a CO atmosphere, selective C(sp3/sup