4652-35-1Relevant academic research and scientific papers
Synthesis and cytotoxicity studies of new analogues of polyamines
Badolo, Lassina,Gelbcke,Dubois,Hanocq
, p. 15 - 19 (2007/10/03)
In order to regulate simultaneously the biosynthesis and the transport of natural polyamines, the synthesis of a series of N-methylated analogues of N,N'-Bis(benzyl)-alkanediamines (propanediamine and butanediamine) was achieved and the cytotoxicity of these compounds on the P388D1 cell line was determined. Experiments were conducted in a growth culture medium 20 μM of 2-mercaptoethanol or 0.1 mM of aminoguanidine. Their cytotoxic effects were compared to those obtained under the same conditions with natural polyamines known as toxic compounds at high concentrations. The IC50 of each compound was found very similar for all experimental conditions (IC50 ~150 μM) at the opposite of spermidine and spermine which were less toxic (IC50 >500 μM) when cells were grown in the presence of aminoguanidine (a specific inhibitor of fetal calf serum's PAO). THe DL-difluoromethylornithine (DEMO) and MDL 72527DA, two well known inhibitors of ornithine decarboxylase (ODC) and Polyamine Oxidase (PAO) respectively, had no toxicity on the P388D1 cells compared to our compounds. Our most toxic compound was N1,N4-Bis(benzyl)-N1,N4-bis(methyl)-1,4-butanediamine (6) with an IC50 of 127 ± 3 μM (in culture medium alone). The synthesis of the β-aminothioether derivative of N-benzylputrescine (11) and the β-aminothiol derivative of N-benzylspermidine (13) were also related. The Compound 11 was tested against the P388D1 cells, and did not show any cytotoxic effect. The N-methyl derivatives should give the advantage to be used at low concentrations than those used to test the DFMO.
Synthesis and Diels-Alder reactions of (E)-6,6-dimethoxy-3-hexen-2-one
Yates, Peter,Douglas, Stephen Paul
, p. 2760 - 2765 (2007/10/02)
Treatment of 3,3-dimethoxypropanal (2) with (acetylmethylene)triphenylphosphorane (4) gives (E)-6,6-dimethoxy-3-hexen-2-one (5).Reaction of 5 with cyclopentadiene, 1,3-cyclohexadiene, anthracene, and 1,3-diphenylisobenzofuran gives Diels-Alder adducts, which on hydrolysis are converted to the corresponding keto aldehydes.Attempts to effect intramolecular aldol condensation of the latter were unsuccessful.Hydrolysis of the exo-acetyl adduct from 1,3-diphenylisobenzofuran with aqueous formic acid gives 4-acetyl-2,3,3a,4,5,9b-hexahydro-5,9b-diphenylnaphthofuran-2,5-diol, via aldehyde formation and hydrolytic cleavage of the ether bridge.The adduct from cyclopentadiene under anhydrous acid conditions give 3-acetyl-9-methoxy-tetracyclo2,4.03,7>nonane (27).
