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

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

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