Synthesis and antitumor evaluation of the presumed cytotoxic metabolites of spermine and N,N'-bis(3-aminopropyl)nonane-1,9-diamine

Abstract

4,14-Diazaheptadecanedialdehyde (2b), the presumed cytoactive metabolite of the novel experimental antitumor agent iV,N'-bis(3-aminopropyl)nonane-1,9-diamine (lb), was synthesized as its dihydrochloride salt and evaluated for in vivo tumor growth inhibition. The same synthetic sequence was also used to prepare 4,9-diazadodecanedialdehyde (2a), the presumed metabolite of the ubiquitous polyamine spermine (la). The bisaldehyde products were characterized by microchemical analysis and ir and nmr spectral data and by conversion to their bis-2,4-dinitrophenylhydrazone derivatives. Studies with 2a and 2b established that they did not undergo spontaneous decomposition to acrolein under a variety of experimental conditions, including those normally employed in cell culture technique..V,./V'-Bis(3-aminopropyl)nonane-1,9-diamine (lb)2 is an experimental antitumor agent of novel chemical structure.

Inter- and intramolecular hydrogen bonds – Structures of 1-methylpyrrole-2-carboxamide and 1-hydroxypyrrole-2-carboxamide

“…Synthesis of MPCA proceeding according to the description given by Israel [26]. One gram (0.007 mol) methyl 1-methylpyrrole-2-carboxylate was dissolved in 50 ml of concentrated NH 4 OH.…”

Structural investigation of 3,5‐disubstituted isoxazoles by 1H‐nuclear magnetic resonance

“…The only unknown compound 4g was synthesized using the sequence of reactions depicted in the Scheme 3 that involves a classical transformation of an ester into a nitrile [43,44]. M. Sechi, L. Sannia, M. Orecchioni, F. Carta, G. Paglietti and N. Neamati Conclusion.…”

Synthesis of New Polyamine Derivatives for Cancer Chemotherapeutic Studies

“…This concept was substantiated by previous reports (26)(27)(28)(29) The urea derivative IVQ was prepared as follows. p-Nitrotrifluoroacetanilide (XVa), prepared from p-nitroaniline and trifluoroacetic anhydride, was reduced to the corresponding amino derivative XVb.…”