884492-66-4

Basic information

• Product Name: (S)-3-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
• Synonyms: (S)-3-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
• CAS NO: 884492-66-4
• Molecular Weight: 326.398
• Mol File: 884492-66-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-3-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one(884492-66-4)
• EPA Substance Registry System: (S)-3-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one(884492-66-4)

Safety Data

• Hazardous Substances Data: 884492-66-4(Hazardous Substances Data)

Upstream product

• 63-91-2 L-phenylalanine 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 14825-82-2 L-phenylalanine-N-carboxyanhydride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Downstream Products

• 1289116-64-8 (S)-3-benzyl-5-phenyl-1-(quinolin-8-ylmethyl)-1H-benzo-[e][1,4]diazepin-2(3H)-one 
• 1289116-63-7 (S)-3-benzyl-1-(biphenyl-2-ylmethyl)-5-phenyl-1H-benzo-[e][1,4]diazepin-2(3H)-one 
• 1289116-61-5 (S)-3-benzyl-1-(biphenyl-4-ylmethyl)-5-phenyl-1H-benzo-[e][1,4]diazepin-2(3H)-one 
• 1289116-62-6 (S)-3-benzyl-1-(biphenyl-3-ylmethyl)-5-phenyl-1H-benzo-[e][1,4]diazepin-2(3H)-one 
• 1289116-60-4 (S)-1,3-dibenzyl-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one 
• 1289116-77-3 (S)-3-benzyl-1-(2-nitrobenzyl)-5-phenyl-1H-benzo[e][1,4]-diazepin-2(3H)-one 
• 1289116-75-1 (S)-3-benzyl-1-(4-nitrobenzyl)-5-phenyl-1H-benzo[e][1,4]-diazepin-2(3H)-one 
• 1289116-83-1 (S)-1-(4-aminobenzyl)-3-benzyl-5-phenyl-1H-benzo[e]-[1,4]diazepin-2(3H)-one 
• 1289116-85-3 (S)-1-(2-aminobenzyl)-3-benzyl-5-phenyl-1H-benzo[e]-[1,4]diazepin-2(3H)-one 
• 1289117-02-7 (S)-3-benzyl-1-(2-oxo-2-(4-(pyrimidin-2-yl)piperazin-1-yl)ethyl)-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one 
• 1289117-03-8 (S)-3-benzyl-1-(2-oxo-2-(4-(pyridin-2-yl)piperazin-1-yl)ethyl)-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one 
• 1289116-67-1 (S)-2-(3-benzyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo-[e][1,4]diazepin-1-yl)acetic acid 
• 1289116-65-9 (S)-2-(3-benzyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-1-yl)acetonitrile 
• 1219505-81-3 (S)-3-benzyl-1-methyl-5-phenyl-1H-benzo[e][1,4]-diazepin-2(3H)-one 

Relevant articles and documents

Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts

Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.

An Atom-Economical Method to Prepare Enantiopure Benzodiazepines with N-Carboxyanhydrides

The development of a rapid, one-pot synthesis of diazepinones with simple reagents is described. N-Carboxyanhydrides (NCAs) are employed as amino acid building blocks that react with o-ketoanilines sequentially as electrophiles and nucleophiles to form diazepinones with water and carbon dioxide as byproducts. Notably, these reactions enable the coupling of stereodefined amino acid derived NCAs without racemization. This method is demonstrated by an improved synthesis of a key intermediate toward a bromodomain and extra-terminal (BET) bromodomain inihibitor.

The design of non-peptide human Bradykinin B2 receptor antagonists employing the benzodiazepine peptidomimetic scaffold

The Bradykinin B2 receptor antagonist HOE 140 (D-Arg-Arg-Pro-Hyp-Gly- Thi-Ser-D-Tic-Oic-Arg) has been used as a template for the de novo design and synthesis of a small number of non-peptide lead compounds based on the 1,4- benzodiazepin-2-one framework. Two of the compounds have been found to exhibit moderate K(i) values of 8.9 and 9.2 μM at the human Bradykinin B2 receptor.