73534-55-1

Usage

Uses

Used in Organic Synthesis:
(3S)-3-methyl-3,4-dihydroquinoxalin-2(1H)-one is used as a starting material and intermediate in organic synthesis for the production of various compounds. Its unique structure and chirality make it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (3S)-3-methyl-3,4-dihydroquinoxalin-2(1H)-one is utilized as a starting material and intermediate for the development of new pharmaceutical drugs. Its structural features and potential biological activities or pharmacological properties make it a promising candidate for drug discovery and design.
Used in Drug Development:
Due to its potential biological activities or pharmacological properties, (3S)-3-methyl-3,4-dihydroquinoxalin-2(1H)-one may have applications in the development of pharmaceutical drugs. Its unique structure and chirality could contribute to the creation of novel therapeutic agents with specific mechanisms of action and potential clinical benefits.

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 167823-32-7 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl α-bromopropionate 
• 1493-27-2 ortho-nitrofluorobenzene 
• 1192307-88-2 (2-methoxy-2-oxo-(S)-1-phenylethyl) α-bromopropanoate 
• 56-41-7 L-alanin 
• 615-36-1 2-bromoaniline 
• 1417715-06-0 O,O'-di(α-bromopropanoyl)-L-tartaric acid diisopropyl ester 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 73938-47-3 ethyl (2S)-<2-bromo-1-oxopropyloxy>propanoate 

Downstream Products

• 14003-34-0 3-methyl-2-oxo-1,2-dihydroquinoxaline 

Relevant academic research and scientific papers

Diacetone-D-glucose-mediated asymmetric syntheses of dihydroquinoxalinones

Asymmetric syntheses of dihydroquinoxalinones by diacetone-D-glucose mediated nucleophilic substitution of α-bromo esters have been investigated. Stereoselective reactions with various 1,2-phenylenediamine nucleophiles in the presence of TBAI and DIEA and

Design, synthesis and biological evaluation of quinoxaline compounds as anti-HIV agents targeting reverse transcriptase enzyme

Infection by human immunodeficiency virus still represents a continuous serious concern and a global threat to human health. Due to appearance of multi-resistant virus strains and the serious adverse side effects of the antiretroviral therapy administered, there is an urgent need for the development of new treatment agents, more active, less toxic and with increased tolerability to mutations. Quinoxaline derivatives are an emergent class of heterocyclic compounds with a wide spectrum of biological activities and therapeutic applications. These types of compounds have also shown high potency in the inhibition of HIV reverse transcriptase and HIV replication in cell culture. For these reasons we propose, in this work, the design, synthesis and biological evaluation of quinoxaline derivatives targeting HIV reverse transcriptase enzyme. For this, we first carried out a structure-based development of target-specific compound virtual chemical library of quinoxaline derivatives. The rational construction of the virtual chemical library was based on previously assigned pharmacophore features. This library was processed by a virtual screening protocol employing molecular docking and 3D-QSAR. Twenty-five quinoxaline compounds were selected for synthesis in the basis of their docking and 3D-QSAR scores and chemical synthetic simplicity. They were evaluated as inhibitors of the recombinant wild-type reverse transcriptase enzyme. Finally, the anti-HIV activity and cytotoxicity of the synthesized quinoxaline compounds with highest reverse transcriptase inhibitory capabilities was evaluated. This simple screening strategy led to the discovery of two selective and potent quinoxaline reverse transcriptase inhibitors with high selectivity index.

Iron- or Zinc-Mediated Synthetic Approach to Enantiopure Dihydroquinoxalinones

A general and efficient synthesis of enantiopure dihydroquinoxalinones has been developed using naturally occurring amino acids as starting materials. The reductive cyclization of N-(o-nitroaryl)amino esters was performed by using iron and zinc metal under mild conditions in a water/ethyl acetate mixture. The corresponding dihydroquinoxalinones were obtained in moderate to high yields and high enantiomeric purity, among which 7 new compounds were unprecedented in the literature.

Metal-free tandem cyclization/hydrosilylation to construct tetrahydroquinoxalines

A one-pot tandem procedure involving cyclization and sequential hydrosilylation of imines and amides under the catalysis of B(C6F5)3 has been developed for the step-economical construction of 1,2,3,4-tetrahydroquinoxalines directly from readily available 1,2-diaminobenzenes, α-ketoesters and low-cost, safe polymethylhydrosiloxane (PMHS). This metal-free approach provides various products in good to excellent yields, and displays a wide range of substrate scope and a high degree of functional group tolerance even to reduction-sensitive moieties. The choice of hydrosilanes is critical to the catalysis, and PMHS has proved to be optimal. Decreasing the amount of PMHS could enable the reaction to stop at the 3,4-dihydroquinoxalin-2(1H)-one stage. The procedure is convenient and scalable, and neither a dried solvent nor an inert atmosphere is required. Moreover, the enantioselective construction of these products was explored, and promising results were achieved.

Diversity-Oriented Synthesis as a Strategy for Fragment Evolution against GSK3β

Traditional fragment-based drug discovery (FBDD) relies heavily on structural analysis of the hits bound to their targets. Herein, we present a complementary approach based on diversity-oriented synthesis (DOS). A DOS-based fragment collection was able to produce initial hit compounds against the target GSK3β, allow the systematic synthesis of related fragment analogues to explore fragment-level structure-activity relationship, and finally lead to the synthesis of a more potent compound.

Solid-Phase Synthesis of 3,4-Dihydroquinoxalin-2(1H)-ones via the Cyclative Cleavage of N-Arylated Carboxamides

We describe a practical (time-efficient, with commercially available building blocks, user friendly reaction conditions, high purity of products) synthesis of pharmacologically relevant quinoxalinones with three points of diversification that takes advantage of solid-phase synthesis and cyclative cleavage. Resin-bound (S)-2-(N-alkyl-2-nitrophenyl)sulfonamide-3-alkyl-N-(2-hydroxyethyl)propanamides, which are accessible from Fmoc-protected α-amino acids, 2-nitrobenzenesulfonyl chloride and alcohols, underwent base-mediated N-arylation. The reduction of the nitro group produced acyclic intermediates that were subjected to acid-mediated cyclative cleavage to yield 3,4-dihydroquinoxalin-2(1H)-ones.

Piperazine amide linker for cyclative cleavage from solid support: Traceless synthesis of dihydroquinoxalin-2-ones

A piperazine amide linker for cyclative cleavage from solid support and its use in the traceless solid-phase synthesis of dihydroquinoxalinones are described. Piperazine was attached to Wang resin via a carbamate linkage and acylated with Fmoc-amino acids. Following Fmoc group removal, resin-bound amines were reacted with 1-fluoro-2-nitrobenzenes. The nitro group of the resulting 2-nitroanilines was reduced, and acyclic precursors, in contrast to traditional ester-type linkage, remained attached to the resin. Target dihydroquinoxalinones were obtained either by acid- or microwave-mediated cyclative cleavage. The synthesis provided crude compounds of high purity and enabled the preparation of stable immobilized linear intermediates. The linker is suitable for combinatorial synthesis of compound libraries.

A general and practical access to chiral quinoxalinones with low copper-catalyst loading

A general, straightforward, and practical access to multi-substituted chiral quinoxalin-2-ones has been achieved based on the copper(I) chloride-dimethylethylenediamine (DMEDA) catalyst system. With the use of 1 mol% copper(I) chloride, structurally diverse quinoxalin-2-ones were generated with high optical purity from readily available starting materials, 2-haloanilines and α-amino acids, in a one-pot manner.

(S)-Mandelate-mediated dynamic kinetic resolution of α-bromo esters for asymmetric syntheses of aminoflavones, dihydroquinoxalinones and dihydrobenzoxazinones

(S)-Mandelate-mediated dynamic kinetic resolution of α-bromo esters in nucleophilic substitution reaction has been investigated. Reactions of various aryl amine nucleophiles in the presence of TBAI and DIEA can provide the substitution products 2 and 7-19