The azulene scaffold from a medicinal chemist's perspective : Physicochemical and in vitro parameters relevant for drug discovery
Abstract
Azulene is a bicyclic scaffold rarely applied in medicinal chemistry. Here we report physicochemical and in vitro parameters relevant for drug discovery for a series of diversely substituted azulenes. We synthesized and characterized several scaffold hopping series of analogously substituted azulenes, indoles and naphthalenes. This enabled a comparison of azulene with the more common scaffolds indole and naphthalene. Our data indicates that undesirably low photostability of azulenes is restricted to certain substitution patterns. Generally, we conclude that azulene is an underused lipophilic bicycle and should be considered as a valuable complement to the collection of medicinal chemistry scaffolds.
Main Authors
Format
Articles
Research article
Published
2022
Series
Subjects
Publication in research information system
Publisher
Elsevier
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-202204262374Use this for linking
Review status
Peer reviewed
ISSN
0223-5234
DOI
https://doi.org/10.1016/j.ejmech.2022.114374
Language
English
Published in
European Journal of Medicinal Chemistry
Citation
- Leino, T. O., Sieger, P., Yli-Kauhaluoma, J., Wallén, E. A., & Kley, J. T. (2022). The azulene scaffold from a medicinal chemist's perspective : Physicochemical and in vitro parameters relevant for drug discovery. European Journal of Medicinal Chemistry, 237, Article 114374. https://doi.org/10.1016/j.ejmech.2022.114374
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Funder(s)
Research Council of Finland
Funding program(s)
Postdoctoral Researcher, AoF
Tutkijatohtori, SA
Additional information about funding
T.O.L. acknowledges the Academy of Finland (grant no. 330800) and the Doctoral Programme in Drug Research of the University of Helsinki for financial support.
Copyright© 2022 the Authors