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Full-Text Articles in Physical Sciences and Mathematics
Chemical Strategies For Drug Development Of Fucose-Truncated Ipomoeassin F Analogues, Melissa Hirsch
Chemical Strategies For Drug Development Of Fucose-Truncated Ipomoeassin F Analogues, Melissa Hirsch
Graduate Theses and Dissertations
Natural product synthesis has many applications in the field of chemical biology, due to the protein binding affinity to the complex three-dimensional structure. However, synthetic and structure-activity relationship studies concerning certain drug targets are scarce. For example, members of the ipomoeassin family have exhibited anti-cancer properties, but cost-effective optimization of these compounds has not yet been extensively studied. Ipomoeassin F, a natural glycoresin isolated from the leaves of the Ipomoea squamosa plant in the Suriname rainforest, has shown high cytotoxicity, with IC50 values measured at the low nanomolar range. Two studies by Postema and Fuerstner have outlined synthesis pathways for …
Conformationally-Controlled Late-Stage Modifications For Sar Studies Of The C-3-Glcp Moiety Of Ipomoeassin F, Lucas Whisenhunt
Conformationally-Controlled Late-Stage Modifications For Sar Studies Of The C-3-Glcp Moiety Of Ipomoeassin F, Lucas Whisenhunt
Graduate Theses and Dissertations
The resin glycoside, ipomoeassin F has been shown to be extremely potent against multiple cancer lines (IC50 = 4.2-36 nM). However, the mechanism of action of this potent and complex natural product is still not fully understood. The α,β-unsaturated esters of the glucosyl moiety have been shown to be vital for the overall cytotoxicity of ipomoeassin F. Nevertheless, the importance of the tigloyl ester of the glucosyl moiety is still largely unknown. This work aimed to study the pharmacophore importance of the tigloyl ester by creating, an efficient, scalable, and flexible synthesis route for various analogs. The 18-linear step synthesis …