16741-80-3

Usage

Uses

Used in Pharmaceutical Industry:
H-CYS(BZL)-OME HCL is used as an amino acid antagonist for targeting specific bacterial strains. Its ability to interfere with bacterial amino acid metabolism can lead to the development of novel antibiotics or antimicrobial agents, particularly against drug-resistant bacteria.
Used in Research and Development:
In the field of research, H-CYS(BZL)-OME HCL serves as a valuable tool for studying bacterial amino acid metabolism and the mechanisms of action of various bacterial pathogens. This can help in the identification of new drug targets and the development of innovative therapeutic strategies to combat bacterial infections.
Used in Drug Synthesis:
H-CYS(BZL)-OME HCL can be utilized as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those targeting bacterial infections. Its unique chemical properties make it a versatile building block for the development of new drugs with improved efficacy and selectivity.
Used in Microbiology:
H-CYS(BZL)-OME HCL can be employed in microbiological studies to understand the role of amino acid antagonists in bacterial growth and survival. This knowledge can be applied to develop strategies for controlling bacterial populations in various settings, such as agriculture, food preservation, and environmental management.

InChI:InChI=1/C11H15NO2S.ClH/c1-14-11(13)10(12)8-15-7-9-5-3-2-4-6-9;/h2-6,10H,7-8,12H2,1H3;1H

Upstream product

• 67-56-1 methanol 
• 3054-01-1 S-benzyl-L-cysteine 
• 100-39-0 benzyl bromide 
• 5068-28-0 (2R)-3-benzylsulfanyl-2-tert-butoxycarbonylamino-propionic acid 
• 55478-08-5 N-[(1,1-dimethylethoxy)-carbonyl]-S-(phenylmethyl)-L-cysteine methyl Ester 
• 100-44-7 benzyl chloride 

Downstream Products

• 20987-51-3 S-benzyl-N-(N²-benzyloxycarbonyl-L-asparaginyl)-L-cysteine methyl ester 
• 856-43-9 N-Trifluoracetyl-glycyl-S-benzyl-L-cystein-methylester 
• 3108-67-6 S-benzyl-N-trifluoroacetyl-L-cysteine methyl ester 
• 22728-88-7 S-benzylcysteine methyl ester 
• 17445-49-7 N-Carbobenzoxytyrosyl-S-benzylcysteine methyl ester 
• 132509-37-6 N-Carbobenzoxytyrosyl-S-benzylcysteinylhydrazide 
• 870266-06-1 (R)-3-benzylsulfanyl-2-{[6-methyl-2-(4-phenylpiperidin-1-yl)pyrimidine-4-carbonyl]amino}propionic acid methyl ester 
• 870266-09-4 (R)-3-benzylsulfanyl-2-[(2-biphenyl-4-yl-6-piperidin-1-yl-pyrimidine-4-carbonyl)amino ]propionic acid methyl ester 

Relevant academic research and scientific papers

Palladium(II) Pincer Complexes of Functionalized Amides with S-Modified Cysteine and Homocysteine Residues: Cytotoxic Activity and Different Aspects of Their Biological Effect on Living Cells

In the search for potential new metal-based antitumor agents, two series of nonclassical palladium(II) pincer complexes based on functionalized amides with S-modified cysteine and homocysteine residues have been prepared and fully characterized by 1D and 2D NMR (1H, 13C, COSY, HMQC or HSQC, 1H-13C, and 1H-15N HMBC) and IR spectroscopy and, in some cases, X-ray diffraction. Most of the resulting complexes exhibit a high level of cytotoxic activity against several human cancer cell lines, including colon (HCT116), breast (MCF7), and prostate (PC3) cancers. Some of the compounds under consideration are also efficient in both native and doxorubicin-resistant transformed breast cells HBL100, suggesting the prospects for the creation of therapeutic agents based on the related compounds that would be able to overcome drug resistance. An analysis of different aspects of their biological effects on living cells has revealed a remarkable ability of the S-modified derivatives to induce cell apoptosis and efficient cellular uptake of their fluorescein-conjugated counterpart, confirming the high anticancer potential of Pd(II) pincer complexes derived from functionalized amides with S-donor amino acid pendant arms.

Structure-Guided Development of Potent Benzoylurea Inhibitors of BCL-XLand BCL-2

The BCL-2 family of proteins (including the prosurvival proteins BCL-2, BCL-XL, and MCL-1) is an important target for the development of novel anticancer therapeutics. Despite the challenges of targeting protein-protein interaction (PPI) interfaces with small molecules, a number of inhibitors (called BH3 mimetics) have entered the clinic and the BCL-2 inhibitor, ABT-199/venetoclax, is already proving transformative. For BCL-XL, new validated chemical series are desirable. Here, we outline the crystallography-guided development of a structurally distinct series of BCL-XL/BCL-2 inhibitors based on a benzoylurea scaffold, originally proposed as α-helix mimetics. We describe structure-guided exploration of a cryptic "p5"pocket identified in BCL-XL. This work yields novel inhibitors with submicromolar binding, with marked selectivity toward BCL-XL. Extension into the hydrophobic p2 pocket yielded the most potent inhibitor in the series, binding strongly to BCL-XL and BCL-2 (nanomolar-range half-maximal inhibitory concentration (IC50)) and displaying mechanism-based killing in cells engineered to depend on BCL-XL for survival.

The synthesis and biological evaluation of novel Danshensu-cysteine analog conjugates as cardiovascular-protective agents

A series of novel amide and thioester conjugates between Danshensu and cysteine derivatives have been designed and synthesized based on the strategy of "medicinal chemical hybridization". Pharmacological evaluation indicated that the amide conjugates 3a/4a/17a and thioester conjugates 6a-d exhibited obvious protective effects on H2O2-induced human umbilical vein endothelial cells (HUVECs). Pretreated with these conjugates could increase glutathione (GSH) activity and decrease malondialdehyde (MDA) level. Further study on mechanism of compound 4a revealed that it was related to its mitochondrial-protective effect and regulation of apoptosis-related proteins expression (Bax, p53, PARP, caspase-3, caspase-9 and Bcl-2). These results indicate that these Danshensu-cysteine analog conjugates possess significant cardiovascular-protective effects and merit further investigation.

Ultrasound accelerated synthesis of proteinogenic and α,α- dialkylamino acid ester salts

A simple and efficient sonochemical esterification of proteinogenic as well as cyclic α,α-dialkyl amino acid methyl and ethyl ester hydrochloride salts employing thionyl chloride and alcohol has been reported. All the amino acid esters made have been obtained in good yield (94-98%) as pure compounds.

HALOALKYL CONTAINING COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS

The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.

S-substituted 2-azido-3-mercapto-propionic acid ester and process for its production and use

The subject matter of the invention are S-substituted 2-azido-3-mercapto-propionic acid esters of the general formula STR1 in which R1 is a methyl or ethyl group and R2 is an unsubstituted or substituted alkyl group, a cycloalkyl group, an unsubstituted or substituted aromatic or heteroaromatic group or a benzyl group, and a process for their production by reaction of a methyl or ethyl ester of 2-chloroacrylic acid with a corresponding thiol to form an S-substituted 2-chloro-3-mercapto-propionic acid ester and subsequently exchanging the chlorine atom with an azido group as well as use of the compounds of formula (I) as intermediate products in the production of D,L-cysteine or derivatives of D,L-cysteine.