Cocrystals of Isoniazid with Polyphenols: Mechanochemical Synthesis and Molecular Structure
Isoniazid is used as anti-tuberculosis drug which possesses functional groups capable of forming hydrogen bonds. A series of cocrystals of isoniazid (INH) with polyphenolic coformers such as catechol (CAT), orcinol (ORC), 2-methylresorcinol (MER), pyrogallol (PYR), and phloroglucinol (PLG) were prep...
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| Format: | Article |
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MDPI AG
2020-07-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/10/7/569 |
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| author | Juan Saulo González-González Ana María Monserrat Martínez-Santiago Francisco Javier Martínez-Martínez María José Emparán-Legaspi Armando Pineda-Contreras Marcos Flores-Alamo Héctor García-Ortega |
| author_facet | Juan Saulo González-González Ana María Monserrat Martínez-Santiago Francisco Javier Martínez-Martínez María José Emparán-Legaspi Armando Pineda-Contreras Marcos Flores-Alamo Héctor García-Ortega |
| author_sort | Juan Saulo González-González |
| collection | DOAJ |
| description | Isoniazid is used as anti-tuberculosis drug which possesses functional groups capable of forming hydrogen bonds. A series of cocrystals of isoniazid (INH) with polyphenolic coformers such as catechol (CAT), orcinol (ORC), 2-methylresorcinol (MER), pyrogallol (PYR), and phloroglucinol (PLG) were prepared by solvent-assisted grinding. Powder cocrystals were characterized by infrared (IR) spectroscopy and X-ray powder diffraction. The crystal structure of the cocrystals revealed the unexpected hydration of the INH-MER cocrystal and the preference of the (phenol) O–H∙∙∙N (pyridine) and (terminal) N-H∙∙∙O (phenol) heterosynthons in the stabilization of the structures. The supramolecular architecture of the cocrystals is affected by the conformation and the substitution pattern of the hydroxyl groups of the polyphenols. |
| first_indexed | 2024-03-10T18:44:11Z |
| format | Article |
| id | doaj.art-0d33f43fa4e84fa493783e4f69249f84 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-10T18:44:11Z |
| publishDate | 2020-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-0d33f43fa4e84fa493783e4f69249f842023-11-20T05:37:25ZengMDPI AGCrystals2073-43522020-07-0110756910.3390/cryst10070569Cocrystals of Isoniazid with Polyphenols: Mechanochemical Synthesis and Molecular StructureJuan Saulo González-González0Ana María Monserrat Martínez-Santiago1Francisco Javier Martínez-Martínez2María José Emparán-Legaspi3Armando Pineda-Contreras4Marcos Flores-Alamo5Héctor García-Ortega6Instituto de Farmacobiología, Universidad de la Cañada, Carretera Teotitlán-San Antonio Nanahuatipán km 1.7 s/n., Paraje Titlacuatitla, Teotitlán de Flores Magón, 68540 Oaxaca, MexicoInstituto de Farmacobiología, Universidad de la Cañada, Carretera Teotitlán-San Antonio Nanahuatipán km 1.7 s/n., Paraje Titlacuatitla, Teotitlán de Flores Magón, 68540 Oaxaca, MexicoFacultad de Ciencias Químicas, Universidad de Colima, km 9 Carretera Colima-Coquimatlán, Coquimatlán, 28400 Colima, MexicoFacultad de Ciencias Químicas, Universidad de Colima, km 9 Carretera Colima-Coquimatlán, Coquimatlán, 28400 Colima, MexicoFacultad de Ciencias Químicas, Universidad de Colima, km 9 Carretera Colima-Coquimatlán, Coquimatlán, 28400 Colima, MexicoFacultad de Química, Universidad Nacional Autónoma de México, 04510 Ciudad de México, MexicoFacultad de Química, Universidad Nacional Autónoma de México, 04510 Ciudad de México, MexicoIsoniazid is used as anti-tuberculosis drug which possesses functional groups capable of forming hydrogen bonds. A series of cocrystals of isoniazid (INH) with polyphenolic coformers such as catechol (CAT), orcinol (ORC), 2-methylresorcinol (MER), pyrogallol (PYR), and phloroglucinol (PLG) were prepared by solvent-assisted grinding. Powder cocrystals were characterized by infrared (IR) spectroscopy and X-ray powder diffraction. The crystal structure of the cocrystals revealed the unexpected hydration of the INH-MER cocrystal and the preference of the (phenol) O–H∙∙∙N (pyridine) and (terminal) N-H∙∙∙O (phenol) heterosynthons in the stabilization of the structures. The supramolecular architecture of the cocrystals is affected by the conformation and the substitution pattern of the hydroxyl groups of the polyphenols.https://www.mdpi.com/2073-4352/10/7/569isoniazidcocrystalpolyphenolshydrogen bondmechanochemistry |
| spellingShingle | Juan Saulo González-González Ana María Monserrat Martínez-Santiago Francisco Javier Martínez-Martínez María José Emparán-Legaspi Armando Pineda-Contreras Marcos Flores-Alamo Héctor García-Ortega Cocrystals of Isoniazid with Polyphenols: Mechanochemical Synthesis and Molecular Structure Crystals isoniazid cocrystal polyphenols hydrogen bond mechanochemistry |
| title | Cocrystals of Isoniazid with Polyphenols: Mechanochemical Synthesis and Molecular Structure |
| title_full | Cocrystals of Isoniazid with Polyphenols: Mechanochemical Synthesis and Molecular Structure |
| title_fullStr | Cocrystals of Isoniazid with Polyphenols: Mechanochemical Synthesis and Molecular Structure |
| title_full_unstemmed | Cocrystals of Isoniazid with Polyphenols: Mechanochemical Synthesis and Molecular Structure |
| title_short | Cocrystals of Isoniazid with Polyphenols: Mechanochemical Synthesis and Molecular Structure |
| title_sort | cocrystals of isoniazid with polyphenols mechanochemical synthesis and molecular structure |
| topic | isoniazid cocrystal polyphenols hydrogen bond mechanochemistry |
| url | https://www.mdpi.com/2073-4352/10/7/569 |
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