392725-04-1

Basic information

• Product Name: 1H-Azepine-1-carboxamide, hexahydro-N-[(4-methoxyphenyl)methyl]-4-[[(2R,3E)-2-methyl-4-phenyl- 3-butenyl]amino]-5-(2-methylpropoxy)-, (4R,5R)-
• CAS NO: 392725-04-1
• Molecular Formula: C30H43N3O3
• Molecular Weight: 493.69
• Mol File: 392725-04-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1H-Azepine-1-carboxamide, hexahydro-N-[(4-methoxyphenyl)methyl]-4-[[(2R,3E)-2-methyl-4-phenyl- 3-butenyl]amino]-5-(2-methylpropoxy)-, (4R,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Azepine-1-carboxamide, hexahydro-N-[(4-methoxyphenyl)methyl]-4-[[(2R,3E)-2-methyl-4-phenyl- 3-butenyl]amino]-5-(2-methylpropoxy)-, (4R,5R)-(392725-04-1)
• EPA Substance Registry System: 1H-Azepine-1-carboxamide, hexahydro-N-[(4-methoxyphenyl)methyl]-4-[[(2R,3E)-2-methyl-4-phenyl- 3-butenyl]amino]-5-(2-methylpropoxy)-, (4R,5R)-(392725-04-1)

Safety Data

• Hazardous Substances Data: 392725-04-1(Hazardous Substances Data)

Upstream product

• 392725-01-8 (4R,5R)-4-((S)-3-Benzyloxy-2-methyl-propylamino)-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 392725-03-0 (4R,5R)-4-[tert-Butoxycarbonyl-((S)-2-methyl-3-oxo-propyl)-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 392725-00-7 (4R,5R)-4-Azido-5-(2-methyl-allyloxy)-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 392724-89-9 (4R,5R)-4-Amino-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 392724-88-8 (4R,5R)-4-Azido-5-hydroxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 392724-97-9 2,3,6,7-tetrahydro-azepine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 132365-02-7 N-benzyl-N-(but-3-enyl)-but-3-en-1-amine 
• 392724-90-2 (4R,5R)-4-[((S)-3-Benzyloxy-2-methyl-propyl)-tert-butoxycarbonyl-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 392725-02-9 (4R,5R)-4-[tert-Butoxycarbonyl-((S)-3-hydroxy-2-methyl-propyl)-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 56651-60-6 4-methoxybenzyl isocyanate 
• 392724-92-4 [(4R,5R)-5-Isobutoxy-1-(4-methoxy-benzylcarbamoyl)-azepan-4-yl]-((E)-(R)-2-methyl-4-phenyl-but-3-enyl)-carbamic acid tert-butyl ester 

Downstream Products

• 392724-84-4 (4R,5R)-4-Isobutoxy-5-[methyl-((E)-(R)-2-methyl-4-phenyl-but-3-enyl)-amino]-azepane-1-carboxylic acid 4-methoxy-benzylamide 

Relevant articles and documents

Design, synthesis, and evaluation of azepine-based cryptophycin mimetics

Cryptophycins, depsipeptides isolated from terrestrial blue-green algae, show potent activity against a variety of tumor cell lines. Given the potential of the cryptophycins for cancer therapy, we developed a new class of non-peptide peptidomimetic, designed to replace the 16-membered macrolide ring with a 7-membered azepine ring for attachment of the cryptophycin side chains with the required spatial orientation to mimic the conformation of the relevant region of the natural product. Monte Carlo conformational analysis revealed excellent overlay of the local minimum structural model 6 and X-ray structure of (+)-cryptophycin-3 (5). Starting from this structural model, we designed and synthesized compounds (+)-25, (+)-30, and (+)-34 as potential mimics of cryptophycins. Compounds (+)-25, (+)-30, and (+)-34 were tested for in vitro cytotoxicity against six human cancer cell lines. Although only modest activities were observed, these results suggested that a new series of bioactive cryptophycin analogues might be available by structural modification of the central ring system of the cryptophycins.