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Synthesis and structural characterization of cocrystals of isoniazid and cinnamic acid derivatives

Mashhadi, Syed Muddassir Ali; Yufit, Dmitri; Liu, Huiyu; Hodgkinson, Paul; Yunus, Uzma

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Authors

Syed Muddassir Ali Mashhadi

Huiyu Liu

Uzma Yunus



Abstract

Isoniazid is a key antitubercular agent which exhibits poor chemical stability in the solid state. Cocrystallization with hydroxyl derivatives of cinnamic acid, which themselves possesses antitubercular and antioxidant activity, may produce solid forms with improved pharmaceutical properties. The complementary nature of the functional groups of isoniazid and the chosen coformers resulted in a high success rate for cocrystal formation. The three previously unknown cocrystal forms, plus a new polymorph were characterized by solid-state NMR, DSC, PXRD and single crystal XRD. Three previously known cocrystals were also synthesized and characterized. NMR chemical shifts were observed to distinguish between a key synthon involving the carboxylic acid of cinnamic acid.

Citation

Mashhadi, S. M. A., Yufit, D., Liu, H., Hodgkinson, P., & Yunus, U. (2020). Synthesis and structural characterization of cocrystals of isoniazid and cinnamic acid derivatives. Journal of Molecular Structure, 1219, Article 128621. https://doi.org/10.1016/j.molstruc.2020.128621

Journal Article Type Article
Acceptance Date Jun 4, 2020
Online Publication Date Jun 8, 2020
Publication Date 2020-11
Deposit Date Jun 9, 2020
Publicly Available Date Jun 8, 2021
Journal Journal of Molecular Structure
Print ISSN 0022-2860
Electronic ISSN 1872-8014
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 1219
Article Number 128621
DOI https://doi.org/10.1016/j.molstruc.2020.128621
Public URL https://durham-repository.worktribe.com/output/1269251

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