294864-69-0

Basic information

• Product Name: 1,1-dimethyl N,N-di(3-(N-phenylmethoxycarbonyl)-N-(3-(phenylmethoxycarbonylamino)propyl)amino)propylcarbamate
• Synonyms: 1,1-dimethyl N,N-di(3-(N-phenylmethoxycarbonyl)-N-(3-(phenylmethoxycarbonylamino)propyl)amino)propylcarbamate
• CAS NO: 294864-69-0
• Molecular Weight: 882.067
• Mol File: 294864-69-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,1-dimethyl N,N-di(3-(N-phenylmethoxycarbonyl)-N-(3-(phenylmethoxycarbonylamino)propyl)amino)propylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-dimethyl N,N-di(3-(N-phenylmethoxycarbonyl)-N-(3-(phenylmethoxycarbonylamino)propyl)amino)propylcarbamate(294864-69-0)
• EPA Substance Registry System: 1,1-dimethyl N,N-di(3-(N-phenylmethoxycarbonyl)-N-(3-(phenylmethoxycarbonylamino)propyl)amino)propylcarbamate(294864-69-0)

Safety Data

• Hazardous Substances Data: 294864-69-0(Hazardous Substances Data)

Upstream product

• 31139-36-3 dibenzyl dicarbonate 
• 294864-68-9 bis-[3-(3-amino-propylamino)-propyl]-carbamic acid tert-butyl ester 

Downstream Products

• 294864-70-3 di(3-(N-phenylmethoxycarbonyl)-N-(3-(phenylmethoxycarbonylamino)propyl)amino)propylamine 
• 294864-72-5 N-(2-aminoethyl)-6-(di(3-(N-phenylmethoxycarbonyl)-N-(3-(phenylmethoxycarbonylamino)propyl)amino)propyl)aminohexanamide 
• 294864-71-4 N-(2-(1,1-dimethylethoxycarbonylamino)ethyl-6-(di(3-(N-phenylmethoxycarbonyl)-N-(3-(phenylmethoxycarbonylamino)propyl)amino)propyl)amino)hexanamide 

Relevant articles and documents

Synthesis and characterisation of polyamine-poly(ethylene glycol) constructs for DNA binding and gene delivery

Improved non-viral vector systems are needed for efficient delivery of DNA to target cell nuclei in gene therapy. A series of linear polyamine-poly(ethylene glycol) (PEG) constructs has been synthesised by reaction of appropriately Boc-protected thermine derivatives with ω-methoxyPEG oxiranylmethyl ethers. Constructs carrying 1-3 MeOPEG units and 0, 2 or 4 N-methyl groups have been prepared by this method. H2N(CH2)3NBoc(CH2)3NBoc(CH2)3NHBoc was prepared efficiently by mono-trifluoroacetylation of thermine, attachment of Boc and removal of the trifluoroacetyl group in one pot. A similar process gave H2N(CH2)3NBoc(CH2)3NBoc(CH2)3NH2. BocMeN(CH2)3NHMe was alkylated by 1,3-dibromopropane to give BocMeN(CH2)3NMe(CH2)3NMe(CH2)3NMeBoc. A cyanoethylation/reduction sequence extended H2N(CH2)3NBoc(CH2)3NBoc(CH2)3NH2 to give H2N(CH2)3NBoc(CH2)3NBoc(CH2)3NBoc(CH2)3NBoc(CH2)3NH2, which was converted to its mono- and di-MeOPEG550 derivatives. Deprotection gave the linear polyamine-MeOPEG constructs. A branched triamine-poly(ethylene glycol) construct was prepared by acylation of (BocHN(CH2)3)2N(CH2)3NH2 with ω-methoxyPEG 550 chloroformate, followed by deprotection. A cyanoethylation/reduction/protection sequence from (H2N(CH2)3)2N(CH2)3NHBoc gave a protected pentamine. Alkylation with Br(CH2)5CONH(CH2)2NHBoc, deprotection, acylation with MeOPEG chloroformate and deprotection gave a pentamine-MeOPEG construct in which the MeOPEG is attached through a linker to the central amine. The linear hexamine construct carrying MeOPEG550 at only one terminus was the most effective DNA-interactive member of the two series in an ethidium displacement assay and was effective in delivering a reporter gene to RIF-1 tumours. Copyright (C) 2000 Elsevier Science Ltd.