20322-09-2

Usage

Uses

Used in Pharmaceutical Industry:
5H-Pyrrolo[2,3-b]pyrazine-7-acetic acid is used as a potential anticancer agent for its ability to inhibit the growth of specific cancer cells. It is being studied for its potential to be developed into new pharmaceutical drugs that could target and treat various types of cancer.
Used in Medicinal Chemistry Research:
5H-Pyrrolo[2,3-b]pyrazine-7-acetic acid serves as a subject of interest in medicinal chemistry for its promising biological activities. Researchers are exploring its potential applications in the development of novel therapeutic agents, leveraging its unique structure and properties to create new drugs with improved efficacy and selectivity.
Used in Drug Synthesis:
As a key intermediate in the synthesis of pharmaceutical compounds, 5H-Pyrrolo[2,3-b]pyrazine-7-acetic acid is utilized in chemical reactions to produce new drug candidates. Its unique heterocyclic structure allows for the creation of a variety of drug molecules with potential therapeutic benefits.
Used in Drug Discovery:
5H-Pyrrolo[2,3-b]pyrazine-7-acetic acid is employed in drug discovery processes to identify new lead compounds with potential therapeutic effects. Its biological activity and chemical properties make it a valuable starting point for the development of innovative pharmaceuticals.
Used in Cancer Research:
In cancer research, 5H-Pyrrolo[2,3-b]pyrazine-7-acetic acid is used to study the mechanisms of action that contribute to its anticancer properties. Understanding these mechanisms can provide insights into the development of more effective cancer treatments and potentially lead to the discovery of new targets for intervention.

InChI:InChI=1/C8H7N3O2/c12-6(13)3-5-4-11-8-7(5)9-1-2-10-8/h1-2,4H,3H2,(H,10,11)(H,12,13)

Upstream product

• 4134-09-2 ethyl N-acetyl-DL-phenylalaninate 
• 18315-86-1 Z-β-ethoxycarbonyl-β-nitrostyrene 
• 1795-96-6 phenylalanine ethyl ester 
• 3532-57-8 acetic acid-(β-nitro-cinnamyl ester) 
• 150-30-1 Phenylalanine 
• 36960-03-9 2-oxo-3-phenylpropyl acetate 
• 100-46-9 benzylamine 
• 1796-04-9 2-Nitro-3-chlor-3-phenyl-propen-⁽²⁾-ol-⁽¹⁾-acetat 
• 15028-44-1 DL-phenylalanine methyl ester 
• 673-06-3 (+)-phenylalanine 
• 13906-90-6 2-benzylaziridine 
• 64-17-5 ethanol 
• 6943-96-0 ethyl 2-(hydroxyimino)-3-phenylpropanoate 
• 37559-18-5 3-phenylprop-2-ynyl acetate 

Relevant academic research and scientific papers

Direct Access to Primary Amines from Alkenes by Selective Metal-Free Hydroamination

Direct and selective synthesis of primary amines from easily available precursors is attractive yet challenging. Herein, we report the rapid synthesis of primary amines from alkenes via metal-free regioselective hydroamination at room temperature. Ammonium carbonate was used as ammonia surrogate for the first time, allowing for efficient conversion of terminal and internal alkenes into linear, α-branched, and α-tertiary primary amines under mild conditions. This method provides a straightforward and powerful approach to a wide spectrum of advanced, highly functionalized primary amines which are of particular interest in pharmaceutical chemistry and other areas.

Nucleophilic RhI Catalyzed Selective Isomerization of Terminal Aziridines to Enamides

The selective isomerization of various terminal N-Boc protected aziridines to enamides was realized using the highly reactive nucleophilic rhodium catalyst C with the Lewis acid LiNTf2 as co-catalyst under moderate conditions. The reaction proceeds smoothly with only 1 molpercent catalyst loading and excellent yields were achieved. An intermediate containing an enamide with a non-conjugated terminal C=C double bond was detected during the course of the reaction, which isomerizes to form the thermodynamically favored 2-amido styrene. Mechanistic insight is gained based on these observations.

Regioselective Fluorination of α-Hydroxy-β-aminophosphonates by Using PyFluor

We report a simple protocol for the synthesis of α-fluoro-β-aminophosphonates by the regioselective fluorination of α-hydroxy-β-aminophosphonates under mild conditions. The fluorination reactions were mediated by the PyFluor reagent and occurred with the retention of configuration. The main products of this reaction were a series of α-fluoro-β-aminophosphonates, which can be used as precursors in the preparation of medicinally important compounds (e.g., dipeptide analogues).

Ligand, metal complex containing ligand, and reaction using metal complex containing ligand

A hydrogen transfer reaction may be more efficiently promoted by using a metal complex represented by Formula (2): (wherein, R1 to R8 are the same or different, and each represents a hydrogen atom, a substituted or unsubstituted alkyl group or the like; or wherein; R1 and R2, R2 and R3, R3 and R4, R4 and R5, and R5 and R6 are respectively bonded to each other to form a bivalent hydrocarbon group; R9 are the same or different, and each represents an alkyl group or cycloalkyl group; M is ruthenium (Ru) or the like; X is a ligand; and n is 0, 1 or 2). More specifically, the metal complex enables a hydrogenation reaction of various substrates having a stable carbonyl group or the like to be advanced with a high yield under mild conditions.

N-substituted benzenepropanamide or benzenepropenamide derivatives for use in the treatment of pain and inflammation

Compounds for use in the treatment or prophylaxis of pain, including acute and chronic pain (e.g., nociceptive pain, neuropathic pain, headaches, migraine), represented by general formula (I) in which: the dotted line represents a single or a double bond; and R5 and R5′ are independently —H, —OH or —OR6, where R6 is a linear or branched C1-C4 alkyl; X is -0-, —CH2O—, —CH2CH2O—, —CH(CH3)CH2O— or —CH2CH(CH3)O—; Z is —CH2CH2O—, —CH(CH3)CH2O— or —CH2CH(CH3)O—; m is an integer of O or 1; and n is an integer of 0-50. The compounds of the invention are also effective for reducing inflammation and may be used alone or in combination with other analgesics.

Probing o-diphenylphosphanyl benzoate (o-DPPB)-directed C - C bond formation: Total synthesis of dictyostatin

Herein, we report a robust total synthesis of dictyostatin. This polyketide natural product has attracted much attention because of its impressive antiproliferative activity against several human cancer-cell lines. We accomplished its synthesis in a highly convergent manner from three fragments of equal complexity, which were prepared on multigram scale. The southern and northwestern subunits were constructed through application of our o-DPPB-directed hydroformylation and allylic substitution methodology, respectively. These methods generated the C6 and C14 stereocenters of dictyostatin with good diastereoselectivities and simultaneously allowed further elaboration of the fragments by Wittig olefination and Sharpless asymmetric epoxidation, respectively. The compelling performance of the hydroformylation and allylic substitution with regard to practicability, selectivity, and scale underline their value for the construction of propionate motifs.

N-Substituted Benzenepropanamide and Benzenepropenamide For Use in the Prevention or the Treatment of Affective Disorders

Compounds for use in the treatment or prophylaxis of an affective disorder, which compound is represented by formula I in which the dotted line represents a single or a double bond; and R5 and R5′ are independently —H, —OH or —OR6, where R6 is a linear or branched C1-C4 alkyl; X is —CH2O—; Z is —CH2OH2O—, —CH(CH3)CH2O— or —CH2CH(CH3)O—; m is 1; and n is an integer of 1-5; or a pharmaceutically acceptable salt, prodrug, metabolite, or hydrate thereof.

Bis(amidate)bis(amido) titanium complex: A regioselective intermolecular alkyne hydroamination catalyst

An efficient and selective bis(amidate)bis(amido) titanium precatalyst for the anti-Markovnikov hydroamination of alkynes is reported. Hydroamination of terminal and internal alkynes with primary alkylamines, arylamines, and hydrazines is promoted by 5-10 mol % of Ti catalyst. Various functional groups are tolerated including esters, protected alcohols, and imines. The in situ generated complex shows comparable catalytic activity, demonstrating its synthetic versatility for benchtop application. Applications of this catalyst for the synthesis of amino alcohols and a one-pot procedure for indole synthesis are described. A mechanistic proposal that invokes turnover-limiting protonolysis is presented to rationalize the observed regioselectivities.

N- SUBSTITUTED BENZENEPROPANAMIDE AND BENZENEPROPENAMIDE FOR USE IN THE PREVENTION OR THE TREATMENT OF AFFECTIVE DISORDERS

Compounds for use in the treatment or prophylaxis of an affective disorder, which compound is represented by formula I in which the dotted line represents a single or a double bond; and R5 and R5' are independently -H, -OH or -OR6, where R6 is a linear or branched C1-C4 alkyl; X is -CH2O-; Z is -CH2ΟΗ2O-,-CH(CH3)CH2O- or -CH2CH(CH3)O-; m is 1; and n is an integer of 1-5; or a pharmaceutically acceptable salt, prodrug, metabolite, or hydrate thereof.

METHOD FOR PRODUCING ALCOHOL BY HYDROGENATING LACTONE AND CARBOXYLIC ACID ESTER IN LIQUID PHASE

Disclosed is a method for producing an alcohol from a lactone or a carboxylic acid ester, which enables to produce an alcohol from a lactone or a carboxylic acid ester under relatively mild conditions with high yield and high catalytic efficiency. This method also enables to produce an optically active alcohol from an optically active lactone or an optically active carboxylic acid ester. Specifically disclosed is a method for producing an alcohol by hydrogen reducing a lactone or a carboxylic acid ester in the presence of a catalyst containing ruthenium and a phosphine compound represented by the following general formula (1): wherein R1 represents a spacer; R2, R3, R4, R5, R6 and R7 independently represent a hydrogen atom, an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group; and R8, R9, R10, R11, R12 and R13 independently represent an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group.