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Preparation of penta-azole containing cyclopeptides: challenges in macrocyclization |
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| Authors: | Delia Hernández Andrés Francesch Fernando Albericio Mercedes Álvarez |
| Institution: | a Barcelona Science Park, Josep Samitier 1-5, E-08028 Barcelona, Spain b Pharma Mar, Avda Reyes Católicos 1, E-28770 Colmenar Viejo, Madrid, Spain c Department of Organic Chemistry, University of Barcelona, E-08028 Barcelona, Spain d Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, E-08028 Barcelona, Spain |
| Abstract: | Herein is described the synthesis of several analogs of the natural product IB-01211 from concatenated azoles, via a biomimetic pathway based on cyclization-oxidation of serine containing peptides combined with the Hantzsch synthesis. The macrocyclization of rigid peptide compounds 1 and 2 to give IB-01211 and its epimer 12b was explored, and the results are compared here to those previously obtained for the macrocyclization of more flexible structures in the syntheses of YM-216391, telomestatin, and IB-01211. Lastly, the preliminary results of anti-tumor activity screening of the synthesized analogs are discussed. |
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