3956-31-8

Basic information

• Product Name: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, phenylmethyl ester, (2S,5R,6R)-
• CAS NO: 3956-31-8
• Molecular Formula: C15H18N2O3S
• Molecular Weight: 306.386
• Mol File: 3956-31-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, phenylmethyl ester, (2S,5R,6R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, phenylmethyl ester, (2S,5R,6R)-(3956-31-8)
• EPA Substance Registry System: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, phenylmethyl ester, (2S,5R,6R)-(3956-31-8)

Safety Data

• Hazardous Substances Data: 3956-31-8(Hazardous Substances Data)

Upstream product

• 87106-41-0 C₁₃H₁₈N₂O₅S*C₆H₁₅N 
• 20425-27-8 (2S,5R,6R)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 
• 65102-83-2 benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-phthalisoimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 551-16-6 6-Aminopenicillanic Acid 
• 59034-26-3 (2S,5R,6R)-benzyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 65102-82-1 2-[(2S,5R,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid 
• 36273-76-4 6ξ-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester 
• 100-39-0 benzyl bromide 

Downstream Products

• 65102-82-1 2-[(2S,5R,6R)-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-6-ylcarbamoyl]benzoic acid 
• 67471-83-4 6β-(4-oxo-pentanoylamino)-penicillanic acid benzyl ester 
• 93553-09-4 benzyl 6β-(2,4,5-trichlophenylsulphonylamino)penicillanate 
• 1316164-14-3 benzyl (2S,5R,6R)-6-[(N-decanoyl-L-prolyl-L-threonyl-L-alanyl-L-asparaginyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]-heptane-2-carboxylate 
• 1374116-84-3 benzyl spiro[penicillanate-6,5'-(3-acetyl-2-pyrazoline)] 
• 1374116-77-4 benzyl spiro[penicillanate-6,5'-(3-acetyl-2-pyrazoline)] 
• 1374116-89-8 benzyl spiro[penicillanate-6,3'-(4,5-dimethoxycarbonyl-3H-pyrazole)] 
• 1374116-90-1 benzyl spiro[penicillanate-6,3'-(5-methoxycarbonyl-3H-pyrazole)] 
• 1374116-97-8 benzyl spiro[penicillanate-6,4'-(7-phenyl-6,8-dioxo-2,3,7-triazabicyclo[3.3.0]oct-2-ene)] 
• 1374116-93-4 benzyl spiro[penicillanate-6,4'-(7-phenyl-6,8-dioxo-2,3,7-triazabicyclo[3.3.0]oct-2-ene)] 
• 1374116-82-1 benzyl spiro[penicillanate-6,5'-(3-cyano-2-pyrazoline)] 
• 1374116-75-2 benzyl spiro[penicillanate-6,5'-(3-cyano-2-pyrazoline)] 
• 1374116-83-2 benzyl spiro[penicillanate-6,5'-(3-ethoxycarbonyl-2-pyrazoline)] 
• 1374116-76-3 benzyl spiro[penicillanate-6,5'-(3-ethoxycarbonyl-2-pyrazoline)] 

Relevant articles and documents

Novel penicillin-type analogues bearing a variable substituted 2-azetidinone ring at position 6: Synthesis and biological evaluation

The synthesis and the biological activity of novel semi-synthetic β-Lactam compounds containing an azetidinone moiety joined to the amino-nitrogen of the (+)-6-aminopenicillanic acid (6-APA) as new antibacterial agents is reported. The synthesized compounds were screened for their in vitro antimicrobial activity against a panel of Gram positive and Gram negative pathogens and environmental bacteria. Tested compounds displayed good antimicrobial activity against all tested Gram positive bacteria and for Staphylococcus aureus and Staphylococcus epidermidis antimicrobial activity resulted higher than that of the reference antibiotic. Additionally, in vitro cytotoxic screening was also carried out indicating that the compounds do not cause a cell vitality reduction effective at concentration next to and above those shown to be antimicrobial.

Synthesis of new β-lactam analogs and evaluation of their histone deacetylase (HDAC) activity

A simple synthesis of the β-lactams 11-13 and 16-17 as novel histone deacetylase (HDAC) inhibitors is described. The key synthetic strategies involved the O-alkylation of 6-APA and the coupling reactions of freshly prepared N-carbobenzyloxy-L-prolines 5 and 6 and 6-aminopenicillanates 8-10 and 15 in high yields. It was found that all compounds show potent growth inhibitory activity on human tumor cell lines, the most potent compound 16 exhibiting an IC50 = 2.1 μM in vitro.