Aliphatic chain-containing macrocycles as diazonamide A analogs

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...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-05, Vol.56 (5), p.586-602
Main Authors: Vitkovska, Viktorija, Zogota, Rimants, Kalnins, Toms, Zelencova, Diana, Suna, Edgars
Format: Article
Language:English
Subjects:
Aliphatic compounds
Amino acids
Analogs
Cancer
Chemistry
Chemistry and Materials Science
Chemotherapy
Health aspects
High temperature effects
Metathesis
Natural products
Organic Chemistry
Pharmacy
Titration calorimetry
Tubulins
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02704-6