143818-55-7

Basic information

• Product Name: 3,3-diethyl-4-<<4-<(1,1-dimethylethoxy)carbonyl>phenyl>oxy>-2-azetidinone
• Synonyms: 3,3-diethyl-4-<<4-<(1,1-dimethylethoxy)carbonyl>phenyl>oxy>-2-azetidinone
• CAS NO: 143818-55-7
• Molecular Weight: 319.401
• Mol File: 143818-55-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3,3-diethyl-4-<<4-<(1,1-dimethylethoxy)carbonyl>phenyl>oxy>-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-diethyl-4-<<4-<(1,1-dimethylethoxy)carbonyl>phenyl>oxy>-2-azetidinone(143818-55-7)
• EPA Substance Registry System: 3,3-diethyl-4-<<4-<(1,1-dimethylethoxy)carbonyl>phenyl>oxy>-2-azetidinone(143818-55-7)

Safety Data

• Hazardous Substances Data: 143818-55-7(Hazardous Substances Data)

Upstream product

• 97-96-1 2-Ethylbutyraldehyde 
• 22014-15-9 1-acetoxy-2-ethyl-1-butene 
• 99-96-7 4-hydroxy-benzoic acid 
• 126997-07-7 3,3-diethyl-4-acetyloxy-azetidin-2-one 
• 25804-49-3 tert-butyl 4-hydroxybenzoate 

Downstream Products

• 143818-83-1 3,3-diethyl-4-<<4-<(1,1-dimethylethoxy)carbonyl>phenyl>oxy>-1-<<<(4-methylphenyl)methyl>amino>carbonyl>-2-azetidinone 
• 143818-79-5 3,3-diethyl-4-<<4-<(1,1-dimethylethoxy)carbonyl>phenyl>oxy>-1-(N-benzyl-N-ethylcarbamoyl)-2-azetidinone 
• 143819-00-5 3,3-diethyl-4-<<4-<(1,1-dimethylethoxy)carbonyl>phenyl>oxy>-1-<<<(4-carbamoylphenyl)methyl>amino>carbonyl>-2-azetidinone 
• 143818-98-8 3,3-diethyl-4-<<4-<(1,1-dimethylethoxy)carbonyl>phenyl>oxy>-1-<<<(4-carboxyphenyl)methyl>amino>carbonyl>-2-azetidinone 
• 127022-00-8 4-[1-(4-Benzyloxy-benzylcarbamoyl)-3,3-diethyl-4-oxo-azetidin-2-yloxy]-benzoic acid 
• 143818-65-9 4-<(4-carboxyphenyl)oxy>-3,3-diethyl-1-<<(4-hydroxy-4-phenylbutyl)amino>carbonyl>-2-azetidinone 
• 143818-68-2 4-<(4-carboxyphenyl)oxy>-3,3-diethyl-1-<<(3-phenoxubutyl)amino>carbonyl>-2-azetidinone 
• 143818-60-4 4-<(4-carboxyphenyl)oxy>-3,3-diethyl-1-<<(6-phenylhexyl)amino>carbonyl>-2-azetidinone 
• 143818-59-1 4-[3,3-Diethyl-4-oxo-1-(5-phenyl-pentylcarbamoyl)-azetidin-2-yloxy]-benzoic acid 
• 143818-63-7 4-<(4-carboxyphenyl)oxy>-3,3-diethyl-1-<<(4-oxo-4-phenylbutyl)amino>carbonyl>-2-azetidinone 
• 143818-67-1 4-[3,3-Diethyl-4-oxo-1-(3-phenoxy-propylcarbamoyl)-azetidin-2-yloxy]-benzoic acid 
• 143818-90-0 4-[3,3-Diethyl-1-(4-nitro-benzylcarbamoyl)-4-oxo-azetidin-2-yloxy]-benzoic acid 
• 143819-07-2 4-{1-[(Benzo[1,3]dioxol-5-ylmethyl)-carbamoyl]-3,3-diethyl-4-oxo-azetidin-2-yloxy}-benzoic acid 
• 143819-01-6 4-{1-[(Biphenyl-4-ylmethyl)-carbamoyl]-3,3-diethyl-4-oxo-azetidin-2-yloxy}-benzoic acid 

Relevant articles and documents

Orally active β-lactam inhibitors of human leukocyte elastase. 2. Effect of C-4 substitution

The effect of changing the C-4 substituent of 3,3-diethyl-1- [(benzylamino)carbonyl]-2-azetidinone on inhibition of HLE and in a model of HLE-induced lung damage in hamsters was explored. Substituents at this position do not appear to interact strongly with HLE with the most potent compounds having k(obs)/[I] = 6900 M-1 s-1. However, substituents at this position had a marked effect on in vivo activity. The greatest oral activity in the lung hemorrhage assay was achieved with C-4 aryl carboxylic acid ethers (60-85% inhibition at 30 mg/kg po). Based upon the established mechanism of inhibition by these compounds, the C-4 substituent would be released, and therefore, the pharmacological potential of these C-4 substituents was of considerable concern. Fortunately, compounds containing 4-hydroxybenzoic acid and 4-hydroxyphenylacetic acid ethers at C-4 were among the most active analogs. These phenolic acids are also found as urinary metabolites in healthy humans. Other heteroaryls at C-4 were also orally active in this model despite relatively modest enzyme activity.