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Aliphatic chain-containing macrocycles as diazonamide A analogs

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Chemistry of Heterocyclic Compounds Aims and scope

Aliphatic alkyl chain-containing 12–14-membered macrocycles have been designed as structural analogs of antimitotic natural product diazonamide A. Macrocycles were synthesized from 5-bromooxazole in 7 to 9 linear steps using Ru-catalyzed ring-closing metathesis as the key transformation. Heat effect of binding to α,β-tubulin tetramer (T4-RB3 complex) has been measured for the synthesized macrocycles by isothermal titration calorimetry method.

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Acknowledgement

This work was funded by ERDF (project No. 1.1.1.1/16/A/281 “Simplified Analogues of Diazonamide A as Anticancer Agents”).

We thank Prof. K. Jaudzems for assistance with NMR experiments and the ITC assay.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga, LV-1006, Latvia

    Viktorija Vitkovska, Rimants Zogota, Toms Kalnins, Diana Zelencova & Edgars Suna

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  1. Viktorija Vitkovska
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  2. Rimants Zogota
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  3. Toms Kalnins
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  4. Diana Zelencova
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  5. Edgars Suna
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Correspondence to Edgars Suna.

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Vitkovska, V., Zogota, R., Kalnins, T. et al. Aliphatic chain-containing macrocycles as diazonamide A analogs. Chem Heterocycl Comp 56, 586–602 (2020). https://doi.org/10.1007/s10593-020-02704-6

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  • DOI: https://doi.org/10.1007/s10593-020-02704-6

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