6653-71-0

Usage

Uses

Used in Pharmaceutical Industry:
N-benzyl-2-bromo-propanamide is used as a chemical intermediate for the synthesis of various pharmaceuticals and organic compounds, contributing to the development of new drugs for different therapeutic applications.
Used in Drug Development:
N-benzyl-2-bromo-propanamide is used as a precursor in the development of drugs, facilitating the creation of novel therapeutic agents for addressing various medical conditions.
Used in Chemical Synthesis:
N-benzyl-2-bromo-propanamide is used as a reagent in chemical synthesis processes, enabling the production of a range of organic compounds for diverse applications.

InChI:InChI=1/C10H12BrNO/c1-8(11)10(13)12-7-9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,12,13)

Upstream product

• 100-46-9 benzylamine 
• 7148-74-5 2-Bromopropionyl chloride 
• 598-72-1 2-Bromopropionic acid 
• 535-11-5 Ethyl 2-bromopropionate 
• 563-76-8 α-bromopropionyl bromide 

Downstream Products

• 122885-43-2 (S)-Pyrrolidine-1,2-dicarboxylic acid 2-(1-benzylcarbamoyl-ethyl) ester 1-tert-butyl ester 
• 79658-55-2 3-benzyl-5-methyl-1,3-oxazolidine-2,4-dione 
• 10264-12-7 N-benzylpropanamide 
• 1161924-13-5 C₁₇H₂₅NO 
• 1360567-23-2 (R)-2-phenoxy-N-benzylpropanamide 
• 1360567-26-5 (R)-N-benzyl-2-(ethylthio)propanamide 
• 131335-55-2 (R)-N-benzyl-2-(benzylamino)propanamide 
• 1360567-29-8 1-(benzylamino)-1-oxopropan-2-yl methanesulfonate 
• 131432-92-3 (S)-(-)-2-bromo-N-benzylpropanamide 
• 1400272-73-2 N-benzyl-2-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylsulfanyl)propionamide 
• 815624-56-7 C₁₆H₁₆ClNO₂ 

Relevant academic research and scientific papers

Comparative conventional and microwave assisted synthesis of heterocyclic oxadiazole analogues having enzymatic inhibition potential

A comparative microwave assisted and conventional synthetic strategies were applied to synthesize heterocyclic 1,3,4-oxadiazole analogues as active anti-enzymatic agents. Green synthesis of compound 1 was achieved by stirring 4-methoxybenzenesulfonyl chloride (a) and ethyl piperidine-4-carboxylate (b). Compound 1 was converted into respective hydrazide (2) by hydrazine and then into 1,3,4-oxadiazole (3) by CS2 on reflux. The electrophiles, N-alkyl/aralkyl/aryl-2-bromopropanamides (6a–p) were synthesized and converted to N-alkyl/aralkyl/aryl-2-propanamide derivatives (7a–p) by reaction with 3 under green chemistry. Microwave assisted method was found to be effective relative to conventional method. 13C-NMR, 1H-NMR and IR techniques were availed to corroborate structures of synthesized compounds and then subjected to screening against lipoxygenase (LOX), α-glucosidase, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. A number of compounds presented better potential against these enzymes. The most active compounds against LOX and α-glucosidase enzymes were subjected to molecular docking study to explore their interactions with the active sites of the enzymes.

Novel Functionalized Amino Acids as Inhibitors of GABA Transporters with Analgesic Activity

Neuropathic pain resistance to pharmacotherapy has encouraged researchers to develop effective therapies for its treatment. γ-Aminobutyric acid (GABA) transporters 1 and 4 (mGAT1 and mGAT4) have been increasingly recognized as promising drug targets for neuropathic pain (NP) associated with imbalances in inhibitory neurotransmission. In this context, we designed and synthesized new functionalized amino acids as inhibitors of GABA uptake and assessed their activities toward all four mouse GAT subtypes (mGAT1-4). According to the obtained results, compounds 2RS,4RS-39c (pIC50 (mGAT4) = 5.36), 50a (pIC50 (mGAT2) = 5.43), and 56a (with moderate subtype selectivity that favored mGAT4, pIC50 (mGAT4) = 5.04) were of particular interest and were therefore evaluated for their cytotoxic and hepatotoxic effects. In a set of in vivo experiments, both compounds 50a and 56a showed antinociceptive properties in three rodent models of NP, namely, chemotherapy-induced neuropathic pain models (the oxaliplatin model and the paclitaxel model) and the diabetic neuropathic pain model induced by streptozotocin; however compound 56a demonstrated predominant activity. Since impaired motor coordination is also observed in neuropathic pain conditions, we have pointed out that none of the test compounds induced motor deficits in the rotarod test.

Enantioselective Palladium-Catalyzed Cross-Coupling of α-Bromo Carboxamides and Aryl Boronic Acids

We herein report an enantioselective palladium-catalyzed cross-coupling between α-bromo carboxamides and aryl boronic acids, generating a series of chiral α-aryl carboxamides in good yields and excellent enantioselectivities. The development of a chiral P,P=O ligand was critical in overcoming the second transmetalation issue and allows the first asymmetric palladium-catalyzed coupling of α-bromo carbonyl compounds.

Switchable Smiles Rearrangement for Enantioselective O-Aryl Amination

Asymmetric assembly of atropisomeric anilines from abundant and readily available precursors is one of the most challenging but valuable processes in organic synthesis. The use of highly efficient Smiles rearrangement to accomplish switchable enantioselec

Microwave-assisted synthesis of triazole derivatives conjugated with piperidine as new anti-enzymatic agents

The current study was aimed for the study of piperidine-based triazole compounds for their biological potential against various enzymes. A novel library of compounds, 9a-r, having piperidine, 1,2,4-triazole, and propanamides was synthesized through consecutive steps including the formation of sulfonamide, hydrazide, 1,2,4-triazole, and thio-ether. Initially, 4-methoxybenzenesulfonyl chloride (1) and ethyl isonipecotate (2) were utilized to develop ethyl 1-(4-methoxyphenylsulfonyl)-4-piperidinecarboxylate (3). The product 3 was converted into respective hydrazide (4) which was further cyclized into 1,2,4-triazole (5) nucleus. A series of propanamides, 8a-r, were synthesized from different amines, 6a-r. These electrophiles, 8a-r, were reacted with compound 5 under conventional and microwave-assisted protocols to acquire the library of hybrids, 9a-r. The structural confirmations were availed by 1H-NMR, 13C-NMR, and IR techniques. The whole series was evaluated for biological potential against acetylcholinesterase (AChE) and α-glucosidase enzymes. The biological evaluation ranges low to high in potential for different compounds based on the structural variations of synthesized compounds. Almost all the compounds remained active against both the enzymes except a few ones. The bovine serum albumin (BSA) binding study demonstrated the flow of drug in the body, and the docking study explained the interactions responsible for active behavior of synthesized compounds.

Novel indole derivative and medicine containing the same (by machine translation)

[A] formation of Amyloid fibrils can be compounds, including therapeutic or prophylactic agent for neurodegenerative disease Amyloid fibrils formation inhibitor compound and of. (I) or its pharmaceutically acceptable compound represented by the formula [a] or a salt or solvate thereof includes the, Amyloid fibrils formation inhibitor. [R1 And R2 Each independently is H, an alkyl group, a cyano group or the like; R3 And R4 Each independently is H, or an alkyl group; R3 And R4 The, joint may form a ring; Ar1 And Ar2 The substituted or unsubstituted heteroaryl group are independently substituted/unsubstituted aryl groups /; X and Y are each independently a single bond, - (=O) - C etc., Z is O or CH2 ; N is an integer of 1 - 3][Drawing] no (by machine translation)

Transition-Metal-Free Coupling of Alkynes with α-Bromo Carbonyl Compounds: An Efficient Approach towards β,γ-Alkynoates and Allenoates

A direct transition-metal-free coupling between alkynes and α-bromo carbonyl compounds has been developed with ultraviolet (UV) light in aqueous media. This method represents a facile approach to synthetically useful β,γ-alkynyl esters and amides stereoselectively from two readily available starting materials. As an example of the synthetic application of the products, the alkynyl esters were readily converted into allenoates. Time for UV! A direct coupling between alkynes and α-bromo compounds has been developed with ultraviolet light in aqueous media (see scheme). This method represents a facile approach to synthetically useful β,γ-alkynyl esters and amides stereoselectively from two readily available starting materials.

Direct amination of phenols under metal-free conditions

Herein, we disclose the metal-free synthesis of arylamines via the direct amination of phenols using aminating reagents. This reaction procedure uses easy accessible aminating reagents and provides a versatile synthetic route to a broad range of arylamines with various functionalities in good to excellent yield. By using a two-step route of amination and oxidative coupling reaction, we synthesized three naturally occurring carbazole alkaloids: murrayafoline A, mukonine, and clausenine from two commercially available phenols. Georg Thieme Verlag Stuttgart · New York.

Design and synthesis of new 8-anilide theophylline derivatives as bronchodilators and antibacterial agents

Theophylline derivatives have long been recognized as potent bronchodilators for the relief of acute asthma. Recently, it was found that bacterial infection has a role in asthma pathogenesis. The present work involves the design and synthesis of 8-substituted theophylline derivatives as bronchodilators and antibacterial agents. The chemical structures of these compounds were elucidated by IR, 1H-NMR, mass spectrometry, and elemental analyses. The bronchodilator activity was evaluated using acetylcholine-induced bronchospasm in guinea pigs, and most of the compounds showed significant anti-bronchoconstrictive activity in comparison with standard aminophylline. In addition, the antibacterial activity of all the target compounds was investigated in vitro against Gram-positive and Gram-negative bacteria using ampicillin as a reference drug. Results showed that some of the tested compounds possessed significant antibacterial activity. A pharmacophore model was computed to obtain useful insight into the essential structural features of bronchodilator activity. A structure activity relationship was also discussed.

Stereoseleetive synthesis of polysubstituted alkenes through a phosphine-mediated three-component system of aldehydes, α-halo carbonyl compounds, and terminal alkenes

A study was conducted to demonstrate stereoselective synthesis of polysubstituted alkenes through a phosphine-mediated three-component system of aldehydes, α-halo carbonyl compounds, and terminal alkenes. Triphenylphosphine, α-halo carbonyl compounds, and methyl acrylate were added to a solution of aldehyde in chloroform or 1-propanol under nitrogen at room temperature. The resulting mixture was stirred at the specified temperature until transformation was completely observed by thin layer chromatography (TLC) analysis. The mixture was cooled to room temperature and purified by column chromatography on silica gel, eluting with petroleum ether/ethyl acetate. The study demonstrated that the first one-pot and three-component reaction of aldehydes, α-haloacetates, and terminal alkenes was developed in the presence of phenylphosphine to produce a wide range of trisubstituted alkenes with significant stereoselectivity.