Synthesis of 7 alpha- and 7 beta-spermidinylcholesterol, squalamine analogues

Bioorg Med Chem Lett. 2004 Aug 16;14(16):4213-6. doi: 10.1016/j.bmcl.2004.06.010.

Abstract

Stereoselective synthesis of squalamine dessulfates analogues, 7 alpha and 7 beta-N-[3N-(4-aminobutyl) aminopropyl]aminocholesterol are reported, using 7 alpha and 7 beta-aminocholesterol as a key intermediate. It's 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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Bronchial Neoplasms / pathology
  • Carcinoma, Non-Small-Cell Lung / pathology
  • Cell Line, Tumor
  • Cholestanols / chemical synthesis*
  • Cholestanols / chemistry
  • Cholestanols / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Lung Neoplasms / pathology

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Cholestanols
  • squalamine