Adducts of N-Heterocyclic Drugs, Niacin, Allopurinol, and Amiloride, with 2,4-Pyridinedicarboxylic Acid Coformer
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BEJAGAM, Shabari Nath, FONARI, Marina, AVERKIEV, Boris B., KHRUSTALEV, Victor N., LINDLINE, Jennifer, TIMOFEEVA, Tatiana. Adducts of N-Heterocyclic Drugs, Niacin, Allopurinol, and Amiloride, with 2,4-Pyridinedicarboxylic Acid Coformer. In: Crystal Growth and Design, 2017, nr. 8(17), pp. 4237-4245. ISSN 1528-7483. DOI: https://doi.org/10.1021/acs.cgd.7b00542
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Crystal Growth and Design
Numărul 8(17) / 2017 / ISSN 1528-7483

Adducts of N-Heterocyclic Drugs, Niacin, Allopurinol, and Amiloride, with 2,4-Pyridinedicarboxylic Acid Coformer

DOI: https://doi.org/10.1021/acs.cgd.7b00542

Pag. 4237-4245

Bejagam Shabari Nath1, Fonari Marina12, Averkiev Boris B.1, Khrustalev Victor N.1, Lindline Jennifer1, Timofeeva Tatiana13
 
1 New Mexico Highlands University, Department of Chemistry, Las Vegas,
2 Institute of Applied Physics, Academy of Sciences of Moldova,
3 ITMO University
 
Disponibil în IBN: 14 februarie 2018


Rezumat

A co-crystallization of three drug molecules, niacin (3-pyridine-carboxylic acid = NIA), allopurinol (pyrazolo(3,4-d)pyrimidin-4-one = ALP), and amiloride (3,5-diamino-6-chloro-pyrazine-2-carbonyl)-guanidine = AMI), with the same coformer, 2,4-pyridinedicarboxylic acid (PDA), resulted in three new crystalline products, (NIA)(PDA) (1), (ALP)2(PDA)·1.5H2O (2), and (AMI)2(PDA)2(H2O)2 (3). The formation of new phases was confirmed by IR spectra and X-ray single-crystal and powder diffraction analysis. The proton transfer resulted in the zwitterionic co-crystal 1. In co-crystal 2, neutral ALP molecules existed in the oxo-tautomeric form. Compound 3 crystallizes as the salt with the guanidinium cationic part as in the started amiloride hydrochloride hydrate, and the PDA coformer as the zwitterionic pyridinium dicarboxylate anion. Thus, the diversity of the PDA coformer ionization states included the neutral, zwitterion, and zwitterion anionic forms. All compounds were layered structures where the heterocyclic molecules were linked in the H-bonded corrugated layers stabilized by the diverse conventional and charge-assisted hydrogen bonds with π-π stacking interactions between the layers supported by the mediated water molecules in 2 and 3.

Cuvinte-cheie
Carboxylation, carboxylic acids, Hydrogen bonds, Organic compounds, Pyridine, single crystals,

Drug products