217440-34-1

Usage

Uses

Used in Chemical Research:
(R)-Methyl-2-Amino-4-pentenoate Hydrochloride is used as a synthetic building block for the creation of diverse chemical compounds, facilitating the development of novel materials and substances with potential applications across various industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (R)-Methyl-2-Amino-4-pentenoate Hydrochloride is utilized as an intermediate in the production of drugs and other bioactive compounds. Its unique structure allows for the development of new therapeutic agents with improved efficacy and selectivity.
Used in Medicinal Chemistry:
(R)-Methyl-2-Amino-4-pentenoate Hydrochloride is employed as a key component in the field of medicinal chemistry, where it contributes to the discovery and optimization of new drug candidates. Its potential applications in drug discovery highlight its importance in advancing pharmaceutical innovation.
Used in Drug Production:
As an important intermediate in drug synthesis, (R)-Methyl-2-Amino-4-pentenoate Hydrochloride plays a vital role in the manufacturing process of various pharmaceuticals. Its presence in the synthesis pathway ensures the production of high-quality and effective drugs for the treatment of various diseases and conditions.

Upstream product

• 67-56-1 methanol 
• 1069-48-3 rac-allylglycine 
• 54594-06-8 D-allylglycine 
• 118169-12-3 Methyl 2-(benzhydrylideneamino)-4-pentenoate 

Relevant academic research and scientific papers

The discovery of allyltyrosine based tripeptides as selective inhibitors of the HIV-1 integrase strand-transfer reaction

From library screening of synthetic antimicrobial peptides, an O-allyltyrosine-based tripeptide was identified to possess inhibitory activity against HIV-1 integrase (IN) exhibiting an IC50 value of 17.5 μM in a combination 3′-processing and strand transfer microtitre plate assay. The tripeptide was subjected to structure-activity relationship (SAR) studies with 28 peptides, incorporating an array of natural and non-natural amino acids. Resulting SAR analysis revealed the allyltyrosine residue was a key feature for IN inhibitory activity whilst incorporation of a lysine residue and extended hydrophilic chains bearing a terminal methyl ester was advantageous. Addition of hydrophobic aromatic moieties to the N-terminal of the scaffold afforded compounds with improved inhibitory activity. Consolidation of these functionalities lead to the development of the tripeptide 96 which specifically inhibited the IN strand-transfer reaction with an IC50 value of 2.5 μM.

Stereodivergent Synthesis of Carbocyclic Quaternary α-Amino Acid Derivatives Containing Two Contiguous Stereocenters

A novel approach to stereodivergent synthesis of carbocyclic α-quaternary amino acid derivatives, bearing two contiguous stereocenters, is proposed through sequential dual Cu/Ir-catalyzed asymmetric allylation and ring-closing metathesis. A variety of five and six-membered carbocyclic α-quaternary amino acid derivatives could be readily achieved in good to high yields with exclusive regioselectivities, excellent diastereoselectivities (13: 1- > 20: 1 dr) and enantioselectivities (generally >99% ee). Of particular note is that the current protocol is also a versatile synthetic tool for the stereodivergent construction of the challenging seven and eight-membered carbocyclic α-amino acid derivatives. All four stereoisomers of these important molecules could be precisely synthesized through the permutation of chiral Cu/Ir catalytic system. The power of this strategy has been demonstrated for the facile access to some biologically active chiral molecules, such as spiro-hydantoins.

Solid-phase synthesis of peptide thioureas and thiazole-containing macrocycles through ru-catalyzed ring-closing metathesis

N-Terminally modified α-thiourea peptides can selectively be synthesized on solid support under mild reaction conditions using N,N′-di-Boc-thiourea and Mukaiyama's reagent (2-chloro-1-methyl-pyridinium iodide). This N-terminal modification applies to the 20 proteinogenic amino acid residues on three commonly used resins for solid-phase synthesis. Complementary methods for the synthesis of α-guanidino peptides have also been developed. The thiourea products underwent quantitative reactions with α-halo ketones to form thiazoles in excellent purities and yields. When strategically installed between two alkene moieties, said thiazole core was conveniently embedded in peptide macrocycles via Ru-catalyzed ring-closing metathesis reactions. Various 15-17 membered macrocycles were easily accessible in all diastereomeric forms using this methodology. The developed "build/couple/pair" strategy is well suited for the generation of larger and stereochemically complete screening libraries of thiazole-containing peptide macrocycles.

Isothiourea-catalyzed enantioselective carboxy group transfer

Transferable skills: Enantiomerically pure isothioureas promote the 0-to C-carboxyl group transfer of oxazolyl carbonates with excellent levels of enantiocontrol (see scheme). The origin of the enantioselectivity of this process was probed mechanistically and rationalized computationally.

Gold-catalyzed cycloisomerizations of ene-ynamides

The gold-catalyzed cycloisomerizations of 1,6-ene-ynamides proceed under mild conditions and lead to cyclobutanones from terminal or trimethylsilyl substituted ynamides, or to carbonyl compounds bearing a 2,3-methanopyrrolidine subunit from substrates pos

BRIDGED ARYL PIPERAZINES DERIVATIVES USEFUL FOR THE TREATMENT OF CNS, GI-URINARY AND REPRODUCTIVE DISORDERS

The present invention is directed to bridged aryl piperazine derivatives, pharmaceutical compositions containing them and their use in the treatment of depression and related disorders. The compounds of the present invention are serotonin transport inhibi

New cyclic peptides via ring-closing metathesis reactions and their anti-bacterial activities

As part of a program investigating cyclic peptides with an internal aromatic hydrophobic scaffold as potential novel anti-bacterial agents, we explored the synthesis of simple tyrosine-based systems. These were prepared via key intermediates containing internal allylglycine and allyltyrosine residues for subsequent ring-closing metathesis reactions. Although the resulting anti-bacterial activity against Staphylococcus aureus was modest, this represents a novel and simple route to this class of compounds. One intermediate acyclic dipeptide precursor showed good activity against S. aureus with an MIC of 7.8 μg/mL. Crown Copyright

COMPOUNDS AND COMPOSITIONS AS CHANNEL ACTIVATING PROTEASE INHIBITORS

The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating channel activating proteases, and methods for using such compounds to treat, ameliorate or prevent a condition associated with a channel activating protease, including but not limited to prostasin, PRSS22, TMPRSS11 (e.g., TMPRSS11B, TMPRSS11E), TMPRSS2, TMPRSS3, TMPRSS4 (MTSP-2), matriptase (MTSP-1), CAP2, CAP3, trypsin, cathepsin A, or neutrophil elastase.

COMPOUNDS AND COMPOSITIONS AS CHANNEL ACTIVATING PROTEASE INHIBITORS

The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating channel activating proteases, and methods for, using such compounds to treat, ameliorate or prevent a condition associated with a channel activating protease, including but not limited to prostasin, PRSS22, TMPRSS11 (e.g., TMPRSS11B, TMPRSS11E), TMPRSS2, TMPRSS3, TMPRSS4 (MTSP-2), matriptase (MTSP-1), CAP2, CAP3, trypsin, cathepsin A, or neutrophil elastase.

PEPTIDIC COMPOUNDS

The present invention provides a compound of formula (I), (II), (III) and (IV) as defined herein and pharmaceutically acceptable derivatives thereof. The present invention further provides use of the compounds of the present invention in the treatment of bacterial infection and in the treatment of HIV infection. Also provided are pharmaceutical compositions comprising the compounds of the present invention.