52815-19-7

Usage

Uses

Used in Medicinal Chemistry:
BOC-DL-3-AMINOBUTYRIC ACID is used as a building block for the synthesis of peptides and proteins, playing a crucial role in the development of new pharmaceutical compounds. Its presence in the formulation process allows for the creation of complex molecular structures with potential therapeutic applications.
Used in Biochemical Research:
In the field of biochemical research, BOC-DL-3-AMINOBUTYRIC ACID is used as a research tool to study the structure and function of proteins. Its incorporation into experimental designs helps researchers understand the mechanisms of protein interactions and their implications in biological processes.
Used in Laboratory Applications:
BOC-DL-3-AMINOBUTYRIC ACID is used as a reagent in various laboratory procedures, such as the synthesis of complex organic compounds and the investigation of chemical reactions involving amino acids. Its availability as a synthetic compound makes it a valuable resource for scientific exploration.
Used in Industrial Applications:
BOC-DL-3-AMINOBUTYRIC ACID is used in the production of specialty chemicals and materials, such as pharmaceutical intermediates and bioactive compounds. Its synthetic nature allows for the customization of its properties to meet specific industrial requirements, making it a versatile component in the manufacturing process.

InChI:InChI=1/C9H17NO4/c1-6(5-7(11)12)10-8(13)14-9(2,3)4/h6H,5H2,1-4H3,(H,10,13)(H,11,12)/p-1/t6-/m0/s1

Upstream product

• 163254-35-1 methyl 3-((tert-butoxycarbonyl)amino)butanoate 
• 2835-82-7 3-aminobutyric acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 762-75-4 tert-butyl formate 
• 848818-76-8 (R,S)-ethyl 3-((tert-butoxycarbonyl)amino)butanoate 

Downstream Products

• 158461-72-4 [2-(2-Methoxy-5-pyridin-2-yl-phenylcarbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester 
• 158461-71-3 [2-(5-Chloro-2-pyridin-2-yl-phenylcarbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester 
• 119289-77-9 2-<2-(N-Boc-3-aminobutyramido)-4-(methoxy)phenyl>pyridine 
• 2835-82-7 3-aminobutyric acid 
• 869337-40-6 [2-(2-bromo-phenylcarbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester 
• 159991-23-8 (R)-3-((tert-butoxycarbonyl)amino)butanoic acid 
• 146514-31-0 tert-butyl N-(3-hydroxy-1-methylpropyl)carbamate 
• 253866-57-8 6-methyl-2-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 1188535-19-4 C₁₅H₂₀Cl₂N₂O₃ 
• 1431533-86-6 tert-butyl (4-(2-(4-(cyclopropylmethoxy)phenyl)-6,7-dihydro[1,3]oxazolo[5,4-c]pyridin-5(4H)-yl)-4-oxobutan-2-yl)carbamate 

Relevant academic research and scientific papers

Bioisosteric Modification of To042: Synthesis and Evaluation of Promising Use-Dependent Inhibitors of Voltage-Gated Sodium Channels

Three analogues of To042, a tocainide-related lead compound recently reported for the treatment of myotonia, were synthesized and evaluated in vitro as skeletal muscle sodium channel blockers possibly endowed with enhanced use-dependent behavior. Patch-clamp experiments on hNav1.4 expressed in HEK293 cells showed that N-[(naphthalen-1-yl)methyl]-4-[(2,6-dimethyl)phenoxy]butan-2-amine, the aryloxyalkyl bioisostere of To042, exerted a higher use-dependent block than To042 thus being able to preferentially block the channels in over-excited membranes while preserving healthy tissue function. It also showed the lowest active transport across BBB according to the results of P-glycoprotein (P-gp) interacting activity evaluation and the highest cytoprotective effect on HeLa cells. Quantum mechanical calculations and dockings gave insights on the most probable conformation of the aryloxyalkyl bioisostere of To042 in solution and the target residues involved in the binding, respectively. Both approaches indicated the conformations that might be adopted in both the unbound and bound state of the ligand. Overall, N-[(naphthalen-1-yl)methyl]-4-[(2,6-dimethyl)phenoxy]butan-2-amine exhibits an interesting toxico-pharmacological profile and deserves further investigation.

Convergent synthesis of (R)-silodosin via decarboxylative cross-coupling

A new approach to Silodosin capitalizing on a radical retrosynthetic strategy to dissect the molecule into two halves is reported. Using a reductive decarboxylative cross-coupling, a simple indoline can be coupled to a chiral pool-derived fragment to arrive at the target in only seven steps (LLS). This route avoids the use of resolution strategies or asymmetric hydrogenation that requires a subsequent Curtius rearrangement to install a key amino functionality.

NOVEL CRYPTOPHYCIN COMPOUNDS AND CONJUGATES, THEIR PREPARATION AND THEIR THERAPEUTIC USE

The present invention relates to cryptophycin compounds of formula (I). The invention also relates to cryptophycin payloads, to cryptophycin conjugates, to compositions containing them and to their therapeutic use, especially as anticancer agents. The inv

Structural analysis of the dual-function thioesterase SAV606 unravels the mechanism of Michael addition of glycine to an α,β-unsaturated thioester

Thioesterases catalyze hydrolysis of acyl thioesters to release carboxylic acid or macrocyclization to produce the corresponding macrocycle in the biosynthesis of fatty acids, polyketides, or nonribosomal peptides. Recently, we reported that the thioesterase CmiS1 from Streptomyces sp. MJ635-86F5 catalyzes the Michael addition of glycine to an α,β-unsaturated fatty acyl thioester followed by thioester hydrolysis in the biosynthesis of the macrolactam antibiotic cremimycin. However, the molecular mechanisms of CmiS1-catalyzed reactions are unclear. Here, we report on the functional and structural characterization of the CmiS1 homolog SAV606 from Streptomyces avermitilis MA-4680. In vitro analysis indicated that SAV606 catalyzes the Michael addition of glycine to crotonic acid thioester and subsequent hydrolysis yielding (R)-N-carboxymethyl-3-aminobutyric acid. We also determined the crystal structures of SAV606 both in ligand-free form at 2.4 ? resolution and in complex with (R)-N-car-boxymethyl-3-aminobutyric acid at 2.0 ? resolution. We found that SAV606 adopts an α/β hotdog fold and has an active site at the dimeric interface. Examining the complexed structure, we noted that the substrate-binding loop comprising Tyr-53–Asn-61 recognizes the glycine moiety of (R)-N-carboxymethyl-3-aminobutyric acid. Moreover, we found that SAV606 does not contain an acidic residue at the active site, which is distinct from canonical hotdog thioesterases. Site-directed mutagenesis experiments revealed that His-59 plays a crucial role in both the Michael addition and hydrolysis via a water molecule. These results allow us to propose the reaction mechanism of the SAV606-catalyzed Michael addition and thioester hydrolysis and provide new insight into the multiple functions of a thioesterase family enzyme.

Design, synthesis, and biological activities of 1-aryl-1,4-diazepan-2-one derivatives as novel triple reuptake inhibitors

A novel series of triple reuptake inhibitors were explored by ligand-based drug design. A cyclic structure was designed from cyclopropane derivative 5 using the core structure of reported monoamine reuptake inhibitors, leading to the formation of the 1-aryl-1,4-diazepan-2-one derivative 23j-S. Compound 23j-S was shown to act as a potent TRI with an excellent ADME-Tox profile. Oral administration of 23j-S significantly enhanced norepinephrine, dopamine, and serotonin levels in the mouse prefrontal cortex and showed significant antidepressant-like activity in tail suspension tests in mouse.

Heterocycle-to-heterocycle route to quinoline-4-amines: Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles

A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn0 or Fe0 dust and HOAc using a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one and 9-amino-3,4-dihydroacridin-1(2H)-one examples were synthesized.

Synthesis of tricyclic nitrogen heterocycles by a sequence of palladium-catalyzed N-H and C(sp3)-H arylations

A range of tricyclic nitrogen heterocycles were synthesized in a straightforward and efficient manner via a sequence involving palladium-catalyzed N-arylation and C(sp3)-H arylation as the key steps. Whereas the C(sp3)-H arylation furnished fused 6,5,6-membered ring systems efficiently, the formation of the more strained 6,5,5-membered systems proved to be more challenging and required a subtle adjustment of the reaction conditions.

Isoxazolodihydropyridinones: 1,3-dipolar cycloaddition of nitrile oxides onto 2,4-dioxopiperidines

Practical and efficient methods have been developed for the diversity-oriented synthesis of isoxazolodihydropyridinones via the 1,3-dipolar cycloaddition of nitrile oxides onto 2,4-dioxopiperidines. A select few of these isoxazolodihydropyridinones were further elaborated with triazoles by copper-catalyzed azide-alkyne cycloaddition reactions. A total of 70 compounds and intermediates were synthesized and analyzed for drug likeness. Sixty-four of these novel compounds were submitted to the NIH Molecular Libraries Small Molecule Repository for high-throughput biological screening.

COMPOUNDS AND METHODS FOR THE TREATMENT OR PREVENTION OF FLAVIVIRUS INFECTIONS

A compound is represented by Structural Formula (I), or a pharmaceutically acceptable salt thereof, wherein the variables of Structural Formula (I) are as described in the specification and the claims. A pharmaceutical composition comprises a compound represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier of excipient. A method of treating a HCV infection in a subject comprises administering to the subject a therapeutically effective amount of a compound represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof. A method of inhibiting or reducing the activity of HCV polymerase in a subject or in a biological in vitro sample comprises administering to the subject or to the sample a therapeutically effective amount of a compound represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof.

New 7,8-dihydro-1,6-naphthyridin-5(6h)-one-derivatives as PDE4 inhibitors

New 7,8-dihydro-1,6-naphthyridin-5(6H)-one derivatives derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of the phosphodiesterase IV (PDE4).