Synthesis of 7α- and 7β-spermidinylcholesterol, squalamine analogues

Stereoselective synthesis of squalamine dessulfates analogues, 7α and 7β-N-[3N-(4-aminobutyl) aminopropyl]aminocholesterol are reported, using 7α and 7β-aminocholesterol as a key intermediate. Itʹs the first example in which the position of spermidine is modified at the steroid ring. These molecules showed a comparable antibacteria and fungi activities to squalamine. Then, they have a cytotoxic activity on a human non-small cell bronchopulmonary carcinoma line (NSCLC-N6).