Synthesis of spermidinylcholestanol and spermidinylcholesterol, squalamine analogues

Several novel squalamine-related polyaminosterols are reported. The synthesis of 7α-N-[3N-(4-aminobutyl)aminopropyl]aminocholestanol <ce:inter-ref xlink:href="sid:S0040402004015789/I" xmlns:xlink="http://www.w3.org/1999/xlink">I</ce:inter-ref>, 6α-N-[3N-(4-aminobutyl)aminopropyl]aminocholestanol <ce:inter-ref xlink:href="sid:S0040402004015789/II" xmlns:xlink="http://www.w3.org/1999/xlink">II</ce:inter-ref>, 7α and 7β-N-[3N-(4-aminobutyl)aminopropyl]aminocholesterol (<ce:inter-ref xlink:href="sid:S0040402004015789/III" xmlns:xlink="http://www.w3.org/1999/xlink">III</ce:inter-ref> and <ce:inter-ref xlink:href="sid:S0040402004015789/IV" xmlns:xlink="http://www.w3.org/1999/xlink">IV</ce:inter-ref>), was accomplished from cholesterol, they provide the first examples in which spermidine is introduced in the B steroidal ring. These molecules showed comparable antibacteria and fungi activities to squalamine, and were cytotoxic on a human non-small cell bronchopulmonary carcinoma line (NSCLC-N6). Therefore, these molecules with antibiotic and cytotoxic activities are promising for immune-compromised patients in cancer chemotherapy. [Copyright &y& Elsevier]