Steroidal Aza-Lariat Ethers: Syntheses and Aggregation Behavior

Abstract Ten steroid-substituted lariat ether compounds have been prepared including one- and two—armed derivatives of aza-15-crown-5 and aza- and diaza-18-crown-6. They include, N-(3-cholesteryloxycarbonyl-methyl)-aza-15-crown-5, 1, N-(3-dihydrocholesteryloxycarbonylmethyl)-aza-15-crown-5, 2, N-(3-cholesteryloxycarbonylmethyl)-aza-18-crown-6, 3, N-(3-dihydrocholesteryloxycarbonylmethyl)-aza-18-crown-6, 4, N-(3-dihydrocholesteryloxycarbonylpropyl)-aza-15-crown-5, 5, N-(3-dihydrocholesteryloxycarbonylpentyl)-aza-15-crown-5, 6, N-(3-dihydrocholesteryloxycarbonylheptyl)-aza-15-crown-5, 7, N-(3-dihydrocholesteryloxycarbonyldecyl)-aza-15-crown-5, 8, N,N′-bis(3-cholestanyloxycarbonyl-methyl)-4,13-diaza-18-crown-6, 9, and N,N′-bis(3-cholestanyloxycarbonyldecyl)-4,13-diaza-18-crown-6, 10. Aqueous suspensions of these monomers were sonicated. Laser light scattering experiments showed that stable, vesicular aggregates formed. Dye entrapment experiments confirmed the vesicular nature of these aggregates in selected ...

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