Novel Isoniazid cocrystals with aromatic carboxylic acids: Crystal engineering, spectroscopy and thermochemical investigations

Autor(es)

Diniz, Luan F. ^[1] ; Souza, Matheus S. ^[1] ; Carvalho, Jr., Paulo S. ^[1] ; da Silva, Cecilia C. P. ^[1] ; D'Vries, Richard F. ^{[1, 2]} ; Ellena, Javier ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Fis Sao Carlos, CP 369, BR-13560970 Sao Carlos, SP - Brazil

^[2] Univ Santiago Cali, Calle 5 62-00, Cali - Colombia

• Tipo de documento: Artigo Científico
• Fonte: Journal of Molecular Structure; v. 1153, p. 58-68, FEB 5 2018.
• Citações Web of Science: 11

Resumo

Four novel cocrystals of the anti-tuberculosis drug Isoniazid (INH), including two polymorphs, with the aromatic carboxylic acids p-nitrobenzoic (PNBA), p-cyanobenzoic (PCNBA) and p-aminobenzoic (PABA) were rationally designed and synthesized by solvent evaporation. Aiming to explore the possible supramolecular synthons of this API, these cocrystals were fully characterized by X-ray diffraction (SCXRD, PXRD), spectroscopic (FT-IR) and thermal (TGA, DSC, HSM) techniques. The cocrystal formation was found to be mainly driven by the synthons formed by the pyridine and hydrazide moieties. In both INH PABA polymorphs, the COOH acid groups are H-bonded to pyridine and hydrazide groups giving rise to the acid center dot center dot center dot pyridine and acid center dot center dot center dot hydrazide heterosynthons. In INH-PNBA and INH PCNBA cocrystals these acid groups are only related to the pyridine moiety. In addition to the structural study, supramolecular and Hirshfeld surface analysis were also performed based on the structural data. The cocrystals were identified from the FT-IR spectra and their thermal behaviors were studied by a combination of DSC, TGA and HSM techniques. (C) 2017 Elsevier B.V. All rights reserved. (AU)

• Processo FAPESP: 12/05616-7 - Caracterização no estado sólido de fármacos de ação anti-convulsionantes e antidepressivos: Planejamento de novas formas cristalinas.
• Beneficiário: Paulo de Sousa Carvalho Júnior
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 15/25694-0 - Obtenção, caracterização e avaliação de novas formas sólidas cristalinas de fármacos usados no tratamento da tuberculose
• Beneficiário: Luan Farinelli Diniz
• Modalidade de apoio: Bolsas no Brasil - Mestrado