158979-29-4

Usage

Structure

A glycine derivative with a tert-butoxycarbonyl (Boc) protecting group attached to the amino group and a propargyl functional group attached to the alpha carbon atom.

Usage

Building block in organic synthesis and peptide chemistry, utilized in the production of various pharmaceuticals, agrochemicals, and other organic compounds, and a valuable intermediate for the synthesis of diverse chemical structures.

Importance

Widely used compound in chemical research and development due to its versatility and significance in organic chemistry.

Upstream product

• 4530-20-5 BOC-glycine 
• 106-96-7 propargyl bromide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 104501-33-9 2-(prop-2-yn-1-ylamino)acetic acid hydrochloric salt 

Downstream Products

• 946055-37-4 2,2'-(3,3'-(1,4-phenylene)bis(prop-2-yne-3,1-diyl))bis(tert-butoxycarbonylazanediyl)diacetic acid 
• 1567373-39-0 tert-butyl (3-(4-chlorophenyl)prop-2-yn-1-yl)(2-(2-(2-ethylphenyl)hydrazinyl)-2-oxoethyl)carbamate 
• 1586755-72-7 tert-butyl (2-chloro-2-(2-(2-ethylphenyl)hydrazono)ethyl)(3-(4-chlorophenyl)prop-2-yn-1-yl)carbamate 
• 1567373-48-1 C₁₅H₁₈BrN₃O₃S 
• 1567370-84-6 3-(4-chlorophenyl)-2-(2-ethylphenyl)-5-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole 
• 1567370-93-7 3-(4-chlorophenyl)-2-(2-ethylphenyl)-5-(pyridin-3-ylcarbonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole 
• 1567371-14-5 3-(4-chlorophenyl)-2-(2-ethylphenyl)-5-(furan-2-ylcarbonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole 
• 1567373-32-3 3-(6-chloropyridin-3-yl)-2-(2-methoxyphenyl)-5-[(1-methylethyl)sulfonyl]-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole 
• 1567373-38-9 2-((t-butoxycarbonyl)(3-(4-chlorophenyl)prop-2-yn-1-yl)amino)acetic acid 

Relevant academic research and scientific papers

Design, Synthesis, and Reactivity of Multidentate Ligands with Rhenium(I) and Rhenium(V) Cores

Synthetic pathways to a range of potentially N3O-tetradentate ligands designed to coordinate to rhenium cores, as well as their coordination behaviors towards different rhenium cores (oxidation states +I and +V) are investigated. Two functionalized N-{[1-(4-R)-1H-1,2,3-triazol-4-yl]methyl}-2-(pyridin-2-ylmethoxy)aniline derivatives L1H (R = methyl acetate) and L2H (R = 4-nitrophenyl) act exclusively as bidentate ligands and lead to the formation of mononuclear tricarbonylrhenium(I) complexes of the general formula [(LH)Re(CO)3Cl] with L = L1 or L2. Both complexes are characterized by 1H NMR and 13C NMR, FTIR spectroscopy, electrospray ionization mass spectrometry, and in the case of [(L2H)Re(CO)3Cl], single-crystal X-ray diffraction. The rhenium is coordinated by three carbonyl groups, a chlorine atom and two nitrogen atoms of a triazole group, and a nitrogen of the aniline ring of the ligand, respectively. A theoretical study shows complex [(L2H)Re(CO)3Cl] is the most stable structural isomer. In addition, the oxorhenium(V) complex [(L3)ReO] is isolated and fully characterized after the reaction of the ReV precursor [ReOCl3(PPh3)2] with L3H3 [methyl 2-(4-{[2-(2-hydroxyphenylamino)-2-oxoethylamino]methyl}-1H-1,2,3-triazol-1-yl)acetate]. Its corresponding 99mTc complex was achieved with a good radiochemical yield (> 90 %). The convenient synthesis of this ligand, coupled with its high affinity for [ReO]3+ and [99mTcO]3+ cores, make it a promising chelator for biomedical applications.

Discovery and Characterization of VU0529331, a Synthetic Small-Molecule Activator of Homomeric G Protein-Gated, Inwardly Rectifying, Potassium (GIRK) Channels

G protein-gated, inwardly rectifying, potassium (GIRK) channels are important regulators of cellular excitability throughout the body. GIRK channels are heterotetrameric and homotetrameric combinations of the Kir3.1-4 (GIRK1-4) subunits. Different subunit combinations are expressed throughout the central nervous system (CNS) and the periphery, and most of these combinations contain a GIRK1 subunit. For example, the predominance of GIRK channels in the CNS are composed of GIRK1 and GIRK2 subunits, while the GIRK channels in cardiac atrial myocytes are made up mostly of GIRK1 and GIRK4 subunits. Although the vast majority of GIRK channels contain a GIRK1 subunit, discrete populations of cells that express non-GIRK1-containing GIRK (non-GIRK1/X) channels do exist. For instance, dopaminergic neurons in the ventral tegmental area of the brain, associated with addiction and reward, do not express the GIRK1 subunit. Targeting these non-GIRK1/X channels with subunit-selective pharmacological probes could lead to important insights into how GIRK channels are involved in reward and addiction. Such insights may, in turn, reveal therapeutic opportunities for the treatment or prevention of addiction. Previously, our laboratory discovered small molecules that can specifically modulate the activity of GIRK1-containing GIRK channels. However, efforts to generate compounds active on non-GIRK1/X channels from these scaffolds have been unsuccessful. Recently, ivermectin was shown to modulate non-GIRK1/X channels, and historically, ivermectin is known to modulate a wide variety of neuronal channels and receptors. Further, ivermectin is a complex natural product, which makes it a challenging starting point for development of more selective, effective, and potent compounds. Thus, while ivermectin provides proof-of-concept as a non-GIRK1/X channel activator, it is of limited utility. Therefore, we sought to discover a synthetic small molecule that would serve as a starting point for the development of non-GIRK1/X channel modulators. To accomplish this, we used a high-throughput thallium flux assay to screen a 100 000-compound library in search of activators of homomeric GIRK2 channels. Using this approach, we discovered VU0529331, the first synthetic small molecule reported to activate non-GIRK1/X channels, to our knowledge. This discovery represents the first step toward developing potent and selective non-GIRK1/X channel probes. Such molecules will help elucidate the role of GIRK channels in addiction, potentially establishing a foundation for future development of therapies utilizing targeted GIRK channel modulation.

Synthesis and characterization of cyclic brush-like polymers by N-heterocyclic carbene-mediated zwitterionic polymerization of N-propargyl N-carboxyanhydride and the grafting-to approach

Cyclic brush-like polymers were synthesized by tandem organo-mediated zwitterionic polymerization and a grafting-to approach. The cyclic polymer backbone, consisting of poly(N-propargylglycine) (c-PNPG), was synthesized by an N-heterocyclic carbene (NHC)-mediated zwitterionic ring-opening polymerization of N-propargyl N-carboxyanhydride. The polymerization proceeds in a quasi-living manner, allowing access to c-PNPG of well-defined chain length. The cyclic architecture of the polymers was verified by size exclusion chromatography (SEC) and mass spectroscopy (MS), as well as scanning probe characterization. Poly(ethylene glycol) functionalized with azido end-groups was subsequently grafted onto the c-PNPG by the copper-mediated azide/alkyne cycloaddition reaction (CuAAC). The side chain grafting density was determined by 1H NMR spectroscopy and SEC analysis. The grafting efficiency is low (19%) when the cyclic backbone is comprised of a c-PNPG homopolymer. The efficiency can be significantly improved (up to 93%) by utilizing cyclic poly(N-propargylglycine)-ran-poly(N-butylglycine) random copolymers (c-PNPG-r-PNBG). This has been attributed to the ease of access to the propargyl groups in c-PNPG and c-PNPG-ran-PNBG: the strong tendency of the former to aggregate in common organic solvents (including the CuAAC reaction medium) restricts access to the propargyl groups.

Bicyclic enol cyclocarbamates inhibit penicillin-binding proteins

Natural products form attractive leads for the development of chemical probes and drugs. The antibacterial lipopeptide Brabantamide A contains an unusual enol cyclocarbamate and we used this scaffold as inspiration for the synthesis of a panel of enol cyclocarbamate containing compounds. By equipping the scaffold with different groups, we identified structural features that are essential for antibacterial activity. Some of the derivatives block incorporation of hydroxycoumarin carboxylic acid-amino d-alanine into the newly synthesized peptidoglycan. Activity-based protein-profiling experiments revealed that the enol carbamates inhibit a specific subset of penicillin-binding proteins in B. subtilis and S. pneumoniae.

PYRROLOPYRAZOLES AS N-TYPE CALCIUM CHANNEL BLOCKERS

Disclosed are compounds, compositions and methods for treating various diseases, syndromes, conditions and disorders, including pain. Such compounds are represented by Formula I as follows: Formula. (I) wherein R1, R2 R3, Q, and G are defined herein.

Synthesis of substituted 2,4,5,6-tetrahydrocyclopenta[c]pyrazoles and 2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles by intramolecular nitrilimine cycloaddition

Both substituted 2,4,5,6-tetrahydrocyclopenta[c]pyrazoles and 2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles have been synthesized by the 3+2 intramolecular dipolar cycloaddition of nitrilimines to alkynes. This cyclization has been extended to more versatile 3-bromo derivatives by the use of alkynylbromides as dipolarophiles.

Synthesis of specific bivalent probes that functionally interact with 5-HT4 receptor dimers

G-protein-coupled receptor dimerization directs the design of new drugs that specifically bind to receptor dimers. Here, we generated a targeted series of homobivalent ligands for serotonin 5-HT4 receptor (5-HT 4R) dimers composed of

Preparation of N-Boc N-alkyl glycines for peptoid synthesis

A series of N-tert-butoxycarbonylated N-allyl, N-propargyl, N-benzyl or branched N-alkyl glycines, useful building blocks for the synthesis of N-alkyl glycine oligomers, have been prepared by N-alkylation of N-Boc glycine or by a two-step method: reductive alkylation and tert-butoxycarbonylation.