Journal article

Synthesis of SMT022357 enantiomers and in vivo evaluation in a Duchenne muscular dystrophy mouse model

Abstract:: Following on from ezutromid, the first-in-class benzoxazole utrophin modulator that progressed to Phase 2 clinical trials for the treatment of Duchenne muscular dystrophy, a new chemotype was designed to optimise its physicochemical and ADME profile. Herein we report the synthesis of SMT022357, a second generation utrophin modulator preclinical candidate, and an asymmetric synthesis of its constituent enantiomers. The pharmacological properties of both enantiomers were evaluated in vitro and in vivo. No significant difference in the activity or efficacy was observed between the two enantiomers; activity was found to be comparable to the racemic mixture.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Babbs, A., Berg, A., Chatzopoulou, M., Davies, K., Davies, S., Edwards, B., Elsey, D., Emer, E., Figuccia, A., Fletcher, A., Guiraud, S., Harriman, S., Moir, L., Robinson, N., Rowley, J., Russell, A., Squire, S., Thomson, J., Tinsley, J., … Wynne, G. (2019). Synthesis of SMT022357 enantiomers and in vivo evaluation in a Duchenne muscular dystrophy mouse model. Tetrahedron, 76(2).

MLA Style

Babbs, A, et al. “Synthesis of SMT022357 Enantiomers and in Vivo Evaluation in a Duchenne Muscular Dystrophy Mouse Model.” Tetrahedron, vol. 76, no. 2, 2019.

Chicago Style

Babbs, A, A Berg, M Chatzopoulou, et al. 2019. “Synthesis of SMT022357 Enantiomers and in Vivo Evaluation in a Duchenne Muscular Dystrophy Mouse Model.” Tetrahedron 76 (2).
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Files:: BabbsetalVoR2019.pdf

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Publisher copy:: 10.1016/j.tet.2019.130819

Authors

+ Babbs, A More by this author

Institution:: University of Oxford
Department:: Physiology Anatomy & Genetics
Role:: Author

+ Berg, A More by this author

Institution:: University of Oxford
Department:: Physiology Anatomy & Genetics
Role:: Author

+ Chatzopoulou, M More by this author

Institution:: University of Oxford
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author
ORCID:: 0000-0003-1886-7705

+ Davies, K More by this author

Institution:: University of Oxford
Department:: Physiology Anatomy & Genetics
Role:: Author

+ Davies, S More by this author

Institution:: University of Oxford
Department:: Chemistry
Sub department:: Organic Chemistry
Oxford college:: Magdalen College
Role:: Author

More authors...

Publisher:: Elsevier
Journal:: Tetrahedron More from this journal
Volume:: 76
Issue:: 2
Article number:: 130819
Publication date:: 2019-11-27
Acceptance date:: 2019-11-22
DOI:: 10.1016/j.tet.2019.130819
EISSN:: 0040-4020
ISSN:: 1464-5416

Language:: English
Keywords:: FFR
Pubs id:: pubs:1079511
UUID:: uuid:7520d452-e81e-41aa-9913-905ec4eea77a
Local pid:: pubs:1079511
Source identifiers:: 1079511
Deposit date:: 2020-01-18
ARK identifier:: ark:/29072/ora_7520d452e81e41aa9913905ec4eea77a

Terms of use

Copyright holder:: Babbs et al
Copyright date:: 2019
Rights statement:: © 2019 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license

Licence:: CC Attribution (CC BY)

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