183444-88-4

Basic information

• Product Name: D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanine tert-butyl ester
• Synonyms: D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanine tert-butyl ester
• CAS NO: 183444-88-4
• Molecular Weight: 514.621
• Mol File: 183444-88-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanine tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanine tert-butyl ester(183444-88-4)
• EPA Substance Registry System: D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanine tert-butyl ester(183444-88-4)

Safety Data

• Hazardous Substances Data: 183444-88-4(Hazardous Substances Data)

Upstream product

• 16874-17-2 L-phenylalanine tert-butyl ester 
• 35661-38-2 N-(9-fluorenylmethoxycarbonyl)-D-alanine 

Downstream Products

• 183444-97-5 N-(2-chloroethyl)-N'-methyl-N'-{2-[D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanyl-L-(N^ω-9-fluorenylmethoxycarbonyllysyl)amino]ethyl}-N-nitrosourea 
• 183444-93-1 ((S)-5-[2-(tert-Butoxycarbonyl-methyl-amino)-ethylcarbamoyl]-5-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-pentyl)-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 183444-90-8 (S)-6-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-{(S)-2-[(R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-phenyl-propionylamino}-hexanoic acid 
• 164115-06-4 N-(2-chloroethyl)-N'-methyl-N'-[2-(D-alanyl-L-phenylalanyl-L-lysyl-amino)ethyl]-N-nitrosourea 
• 183444-89-5 D-(N-9-fluorenylmethoxycarbonylalanyl)-L-phenylalanine 

Relevant articles and documents

An approach towards more selective anticancer agents

A promising approach towards better targeted anticancer drug therapy takes advantage of enhanced expression of proteases associated with human malignancies. Especially plasminogen activator activity has been found to be substantially increased, leading to an enhanced activity of the serine protease plasmin. Bifunctional alkylating agents, such as N-(2-chloroethyl)-N-nitrosoureas, display broad spectrum anticancer activity, but also exhibit considerable systemic toxicity. We describe here the synthesis of new N-nitrosourea-based prodrugs designed to become activated by tumor-associated proteases, to provide for enhanced antitumor activity and reduced systemic toxicity. Tripeptides representing substrates for plasmin were linked by an amide bond to N'-(2-aminoethyl)-N-(2-chloroethyl)-N-nitrosourea and the corresponding N'-methyl derivative. Synthesis and plasmin-triggered decomposition of these new tripeptide conjugates is described. Cancer cells expressing high plasminogen activator activity are highly sensitive to the new prodrugs in the presence of plasminogen, but not in its absence.