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Synthesis and conformational study of triazole-linked bis-spirostanic conjugates

AuthorsPérez-Labrada, Karell; Morera, Cercis; Brouard, Ignacio ; Llerena, Raciel; Rivera, Daniel G.
KeywordsCycloaddition reactions
Conformational study
Click chemistry
Issue Date20-Mar-2013
CitationTetrahedron Letters 54(12): 1602-1606 (2013)
AbstractA 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.
Publisher version (URL)https://doi.org/10.1016/j.tetlet.2013.01.058
Identifiersdoi: 10.1016/j.tetlet.2013.01.058
issn: 0040-4039
Appears in Collections:(IPNA) Artículos
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