Synthesis of spermidinylcholestanol and spermidinylcholesterol, squalamine analogues

Abstract Several novel squalamine-related polyaminosterols are reported. The synthesis of 7α- N -[3 N -(4-aminobutyl)aminopropyl]aminocholestanol I , 6α- N -[3 N -(4-aminobutyl)aminopropyl]aminocholestanol II , 7α and 7β- N -[3 N -(4-aminobutyl)aminopropyl]aminocholesterol ( III and IV ), 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.