16741-80-3

Basic information

• Product Name: H-CYS(BZL)-OME HCL
• Synonyms: L-Cys(Bzl)-OMe·HCl;BENZYL-L-CYSTEINE METHYL ESTER HYDROCHLORIDE;H-CYS(BZL)-OME HCL;CYSTEINE(BZL)-OME HCL;S-BENZYL-L-CYSTEINE METHYL ESTER HYDROCHLORIDE;S-BENZYL-L-CYSTEINE METHYL ESTER HYDROCHLORIDE SALT;H-Cys(Bzl)-OMe.HCI;S-benzyl-L-cysteine methyl ester*hydrochloride cr
• CAS NO: 16741-80-3
• Molecular Formula: C₁₁H₁₆NO₂S*Cl
• Molecular Weight: 261.77
• EINECS: 240-803-5
• Product Categories: Amino Acids;Amino Acids and Derivatives;Amino Acid Derivatives
• Mol File: 16741-80-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 160-162 °C(Solv: methanol (67-56-1); ethyl ether (60-29-7))
• Boiling Point: 339.8 °Cat 760mmHg
• Flash Point: 159.3 °C
• Appearance: crystalline
• Density: 1.165 g/cm³
• Vapor Pressure: 9E-05mmHg at 25°C
• Storage Temp.: −20°C
• CAS DataBase Reference: H-CYS(BZL)-OME HCL(CAS DataBase Reference)
• NIST Chemistry Reference: H-CYS(BZL)-OME HCL(16741-80-3)
• EPA Substance Registry System: H-CYS(BZL)-OME HCL(16741-80-3)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 16741-80-3(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline

Uses

S-Benzyl-L-cysteine Methyl Ester Hydrochloride is a potential amino acid antagonists in bacteria

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

• 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 
• 100-39-0 benzyl bromide 
• 67-56-1 methanol 
• 3054-01-1 S-benzyl-L-cysteine 

Downstream Products

• 20987-51-3 S-benzyl-N-(N²-benzyloxycarbonyl-L-asparaginyl)-L-cysteine methyl ester 
• 1400221-84-2 N-((R)-3-benzylthio-1-methoxy-1-oxo-2-propanyl)-3-(3,4-diacetoxyphenyl)propanamide 
• 1400221-87-5 N-((R)-3-benzylthio-1-methoxy-1-oxo-2-propanyl)-3-((3,4-methylenedioxy)phenyl)propanamide 
• 1400221-81-9 N-((R)-3-benzylthio-1-methoxy-1-oxo-2-propanyl)-2-acetoxy-3-(3,4-methylenedioxyphenyl)propanamide 

Relevant articles and documents

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.

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.

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.