Synthesis and conformational study of triazole-linked bis-spirostanic conjugates
A general approach based on the CuI-catalyzed azide–alkyne 1,3-dipolar cycloaddition reaction was implemented for the conjugation of two spirostanic steroids. This process provides rapid access to a small library of triazole-based bis-spirostanic conjugates with varied functionalization patterns as well as different stereochemistry of the linkage. The approach proved high efficiency even with the use of sterically hindered 3α-azido-spirostanes. A molecular modeling study was performed to determine the conformational characteristics of the bis-spirostanic conjugates as well as to address the structural resemblance with the potent anticancer bis-spirostanic conjugates cephalostatins and ritterazines. Considering its efficiency and versatility, this approach shows promise for the discovery of novel bis-steroidal conjugates with applications in medicinal chemistry.
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | artículo biblioteca |
| Language: | English |
| Published: |
Elsevier
2013-03-20
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| Subjects: | Cycloaddition reactions, Conformational study, Click chemistry, Steroids, Spirostanes, |
| Online Access: | http://hdl.handle.net/10261/178834 http://dx.doi.org/10.13039/501100003339 |
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