183121-23-5

Basic information

• Product Name: 3-[4-(Dimethylamino)benzylsulfanyl]-2(R)-[2(S)-methyl-3-sulfanylpropionamido]propionic acid
• Synonyms: SA-6541; S-[4-(Dimethylamino)benzyl]-N-[2(S)-methyl-3-sulfanylpropionyl]-L-cysteine
• CAS NO: 183121-23-5
• Molecular Formula: C₁₆H₂₄N₂O₃S₂
• Molecular Weight: 356.50928
• Mol File: 183121-23-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-[4-(Dimethylamino)benzylsulfanyl]-2(R)-[2(S)-methyl-3-sulfanylpropionamido]propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[4-(Dimethylamino)benzylsulfanyl]-2(R)-[2(S)-methyl-3-sulfanylpropionamido]propionic acid(183121-23-5)
• EPA Substance Registry System: 3-[4-(Dimethylamino)benzylsulfanyl]-2(R)-[2(S)-methyl-3-sulfanylpropionamido]propionic acid(183121-23-5)

Safety Data

• Hazardous Substances Data: 183121-23-5(Hazardous Substances Data)

Upstream product

• 183121-49-5 N-tert-butoxycarbonyl-S-(4-dimethylamino)benzyl-L-cysteine 
• 42727-83-3 (R)-2-Amino-3-(4-dimethylamino-benzylsulfanyl)-propionic acid 
• 1703-46-4 N,N-dimethyl-4-hydroxymethylaniline 
• 183121-03-1 N-[(2S)-3-benzoylthio-2-methylpropionyl]-S-(4-dimethylamino)benzyl-L-cysteine 

Relevant articles and documents

Synthesis and biological evaluation of N-mercaptoacylcysteine derivatives as leukotriene A4 hydrolase inhibitors

We studied synthetic modifications of N-mercaptoacylamino acid derivatives to develop a new class of leukotriene A4 (LTA4) hydrolase inhibitors. S-(4-Dimethylamino)benzyl-l-cysteine derivative 2a (SA6541) showed inhibitory activity against LTA4 hydrolase (IC50, 270 nM) and selectivity over other metallopeptidases except angiotensin-converting enzyme (ACE, IC50, 520 nM). Modification at the para-substituent of the phenyl ring of compound 2a improved LTA4 hydrolase inhibitory activity as well as selectivity over ACE. Finally, we obtained S-(4-cyclohexyl)benzy-l-cysteine derivatives 11l and 16i as potent and selective LTA4 hydrolase inhibitors.

Involvement of leukotriene B4 in murine dermatitis models.

Leukotriene B4 (LTB4) is a product of the 5-lipoxygenase pathway of arachidonic acid (AA) metabolism. LTB4 is a potent chemotactic factor for neutrophils and has been postulated to play an important role in a variety of pathological conditions including rheumatoid arthritis, psoriasis, and inflammatory bowel disease. To investigate the role of LTB4 in dermatitis, we used S-(4-dimethylaminobenzyl)-N-[(2S)-3-mercapto-2-methylpropionyl]-L- cysteine (SA6541), a potent leukotriene A4 (LTA4) hydrolase inhibitor. SA6541 inhibited LTB4 production with an IC50 value of 270 nM in vitro. 5-Hydroperoxyeicosatetraenoic acid (5-HPETE) or AA injection induced LTB4 production and neutrophil influx in mouse ear. SA6541 inhibited 5-HPETE- and AA-induced LTB4 production and neutrophil influx in mouse ear when administered orally at a dose of 50 mg/kg. SA6541 also inhibited 5-HPETE-induced prostaglandin E2 (PGE2) production, probably by an indirect effect through the inhibition of LTB4 production. These results suggest that LTB4 may be important in the pathogenesis of dermatitides such as psoriasis.