209115-54-8Relevant academic research and scientific papers
Novel oxa-spermine homologues: synthesis and cytotoxic properties.
Kuksa, Vladimir A,Pavlov, Valentin A,Kong Thoo Lin, Paul
, p. 691 - 697 (2007/10/03)
New oxa-spermine homologues 5-9 were synthesised and their anticancer properties were evaluated against a broad spectrum of cancer cells. All compounds, except 9 showed average GI(50) values in the range of 1.89-7.56 microM. SAR studies showed that the cytotoxic activity of these novel oxa-spermines depended on the length of the alkyl chain, the position of the oxa-amino functionality and also, on the type of sulphonamido group in the molecule. Although the mechanism of action of these compound remains to be elucidated, it would appear that direct drug-DNA interactions are not involved in the mode of action of these drugs.
The synthesis of novel oxa-azamacrocycles
Kuksa, Vladimir,Marshall, Colin,Wardell, Solange,Kong Thoo Lin, Paul
, p. 1034 - 1038 (2007/10/03)
Novel protected oxa-azamacrocycles 6a-f, 7a,c-f have been prepared by direct alkylation reaction between α,ω-bis[(2- mesitylsulfonyl)aminooxy]alkanes 2a-c and α,ω-bis(tosyl)alkanediols 3a,b in the presence of K2CO3 to give a mixture of the 1:1 (small macrocycles 6a- f) and 2:2 (large macrocycles 7a,c-f) adducts. Another method involved the reaction between bis (sulfonyl)amides 2a,b and ω-bromoalkanols 4a,b to give bis-alkanols 5a,b which were subsequently condensed with 2a,b under Mitsunobu conditions to give solely large macrocycles 7a,d in high yields. Macrocycle 7d was deprotected with HBr/HOAc to yield 8 as the tetrahydrobromide salt which was converted into its free base with methanolic KOH.
The Synthesis of Oxa-Analogues and Homologues of Naturally Occuring Polyamines
Lin, P. Kong Thoo,Kuksa, V. A.,Maguire, N. M.
, p. 859 - 866 (2007/10/03)
A number of polyamine oxa-analogues 14a-d, 19 have been synthesized.Spermidine oxa-analogues and homologues 14 were made from N-(aminooxypropyl)phthalimide 8a which was obtained either from the Fmoc-deprotection of N-phthalimide 4a or from the reaction between 3-bromopropylamine and N-hydroxyphthalimide, both reactions involving an unusual rearrangement mechanism.Sulphonated derivatives 9, 16, upon Mitsunobu condensation with N-protected 3-aminopropanol or N-alkylation with N-(bromoalkyl)phthalimides, afforded the fully protected spermidine and spermine oxa-analogues.Subsequent sequential deprotection gave spermidine analogues 14.Using the same strategy, spermine oxa-analogues 19 was synthesised. - Keywords: polyamines; oxa-analogues of polyamines; polyamine homologues; rearrangement; synthesis
