15180-22-0

Basic information

• Product Name: (2S,5S)-2-Benzyl-5-methylpiperazine-3,6-dione
• Synonyms: (2S,5S)-2-Benzyl-5-methylpiperazine-3,6-dione;(3S,6S)-3-Benzyl-6-methyl-2,5-piperazinedione
• CAS NO: 15180-22-0
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25
• Mol File: 15180-22-0.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,5S)-2-Benzyl-5-methylpiperazine-3,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-2-Benzyl-5-methylpiperazine-3,6-dione(15180-22-0)
• EPA Substance Registry System: (2S,5S)-2-Benzyl-5-methylpiperazine-3,6-dione(15180-22-0)

Safety Data

• Hazardous Substances Data: 15180-22-0(Hazardous Substances Data)

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 150582-57-3 (S)-4-methyl-2,2-bis-trifluoromethyl-oxazolidin-5-one 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 35661-40-6 N-Fmoc L-Phe 
• 40298-89-3 L-alanyl-L-phenylalanine methyl ester 
• 3235-14-1 (S)-2-((S)-2-Benzyloxycarbonylamino-propionylamino)-3-phenyl-propionic acid methyl ester 
• 2280-66-2 N-tert-butyloxycarbonylalanylphenylalanine methyl ester 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 1416817-74-7 C₁₄H₁₇N₃O₃ 
• 1115-59-9 (S)-alanine ethyl ester hydrochloride 
• 15761-38-3 L-N-Boc-Ala 
• 15136-29-5 (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)propanoate 

Downstream Products

• 17585-69-2 L-phenylalanine hydrochloride 
• 6003-05-0 L-alanine hydrochloride 

Relevant articles and documents

Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens

Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure–activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.

Synthesis and conformational characterization of diketopiperazines bearing a benzyl moiety

Diketopiperazines bearing a benzyl moiety with different para-substituents were synthesized and analyzed by 1HNMR spectroscopy. All of these diketopiperazines were found to adopt a folded conformation according to the upfield chemical shift of the cis-proton (cis to the benzyl moiety) due to a shielding effect in the 1HNMR spectra. An intramolecular CH-π interaction appears to be an important factor for the folded conformation due to the effects of para-substituents on the benzyl group.

Catalytic asymmetric synthesis of substituted morpholines and piperazines

Under two conditions: Hydroamination catalyzed by group 4 metals is featured in the modular and enantioselective synthesis of 3-substituted morpholines and the diastereoselective synthesis of 2,5-substituted piperazines. Copyright