137965-31-2

Basic information

• Product Name: (2S,5S,1'R)-1-Benzoyl-5-<1'-hydroxy-2'-(4''-nitrophenyl)ethyl>-2-tert-butyl-3-methylimidazolidin-4-one
• Synonyms: (2S,5S,1'R)-1-Benzoyl-5-<1'-hydroxy-2'-(4''-nitrophenyl)ethyl>-2-tert-butyl-3-methylimidazolidin-4-one
• CAS NO: 137965-31-2
• Molecular Weight: 425.484
• Mol File: 137965-31-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,5S,1'R)-1-Benzoyl-5-<1'-hydroxy-2'-(4''-nitrophenyl)ethyl>-2-tert-butyl-3-methylimidazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S,1'R)-1-Benzoyl-5-<1'-hydroxy-2'-(4''-nitrophenyl)ethyl>-2-tert-butyl-3-methylimidazolidin-4-one(137965-31-2)
• EPA Substance Registry System: (2S,5S,1'R)-1-Benzoyl-5-<1'-hydroxy-2'-(4''-nitrophenyl)ethyl>-2-tert-butyl-3-methylimidazolidin-4-one(137965-31-2)

Safety Data

• Hazardous Substances Data: 137965-31-2(Hazardous Substances Data)

Upstream product

• 1460-05-5 p-nitrophenylacetaldehyde 
• 101055-56-5 (2S)-1-benzoyl-2-(1,1-dimethylethyl)-3-methyl-4-imidazolidinone 
• 101055-57-6 (2R)-1-benzoyl-2-(1,1-dimethylethyl)-3-methyl-4-imidazolidinone 

Downstream Products

• 137965-30-1 (2R,3S)-2-amino-3-hydroxy-4-(4-nitrophenyl)butanoic acid 
• 99268-38-9 (2S,3R)-2-amino-3-hydroxy-4-(4-nitrophenyl)butanoic acid 
• 137965-33-4 (3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate 
• 138125-73-2 (2S,3R)-2-<<(2-Nitrophenyl)sulfenyl>amino>-3-hydroxy-4-(4-nitrophenyl)butanoic acid 
• 138125-74-3 (3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-nitrophenyl)methyl>-2-oxetanone 

Relevant articles and documents

Synthesis, Stability, and Antimicrobial Activity of (+)-Obafluorin and Related β-Lactone Antibiotics

Optically pure obafluorin (1), an antibacterial agent from Pseudomonas fluorescens, was synthesized in six steps via lactonization of N--(2S,3R)-2-amino-3-hydroxy-4-(4-nitrophenyl)butanoic acid (12a), which was prepared in a stereospecific manner from 4-nitrophenylacetaldehyde (9a) and (S)-1-benzoyl-2-tert-butyl-3-methyl-4-imidazolidinone (7).A series of analogues was then synthesized in order to probe structural features required for antibacterial activity as well as those responsible for the hydrolytic decomposition of 1 to the corresponding hydroxy acid 23a.Analogues 22b and 22c wherein the nitro group of 1 is replaced with hydrogen and chlorine, respectively, were prepared in a fashion similar to 1, as were the N-acetyl, N-benzoyl, and N-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl (ATMO) derivatives 24a-c.The tosylate salt of L-threonine-β-lactone (21) was transformed to a series of N-acylated derivatives including the following: 22d (2,3-dihydroxybenzoyl), 25 (2-hydroxybenzoyl), 27 (3,4-dihydroxybenzoyl), 29 (4'-methyl-2,2'-bipyridine-4-carbonyl), 31 (ε-(L-α-aminoadipoyl)), 34 ((N'-2,3-dihydroxybenzoyl)-β-alanyl), 35 (bromoacetyl), 36 ((6-purinylthio)acetyl), and 37 ((4-pyridylthio)acetyl).The results show that α-amino β-lactones bearing an N-acyl group with an o- or p-hydroxybenzoyl moiety are especially prone to decomposition under aqueous conditions and that this effect is enhanced by replecement of the 4-nitrobenzyl group on the oxetanone ring of 1 with a methyl.The N-(3,4-dihydroxybenzoyl)-L-threonine β-lactone (27) converts slowly in the solid state to (4S,5S)-2-(3,4-dihydroxybenzoyl)-5-methyl-2-oxazoline-4-carboxylic acid (39b), which hydrolyzes rapidly in 4:1 CD3CN:D2O to O-(3,4-dihydroxybenzoyl)-L-allothreonine (38b).Direct hydrolysis of 27 to 38b under the same conditions has a half-life of 2.4 days.Preliminary assays for antibacterial activity indicate that 29 has nearly comparable activity to obafluorin (1) but is much more stable.The (2-nitrophenyl)sulfenyl β-lactones 14 and 41, as well as the N-(phenylsulfenyl)-L-threonine β-lactone (44), are the most active agents in the biological assays.