Supramolecular hydrogen-bonding patterns in 1:1 cocrystals of 5-fluorouracil with 4-methylbenzoic acid and 3-nitrobenzoic acid.
作者： Marimuthu Mohana , Packianathan Thomas Muthiah , Colin D. McMillen
DOI: 10.1107/S2053229617001486
关键词:
摘要: The design of a pharmaceutical cocrystal is based on the identification specific hydrogen-bond donor and acceptor groups in active ingredients (APIs) order to choose `complementary interacting' molecule that can act as an efficient coformer. 5-Fluorouracil (5FU) pyrimidine derivative with two N—H donors C=O acceptors shows diversity hydrogen-bonding motifs. Two 1:1 cocrystals 5-fluorouracil (5FU), namely 5-fluorouracil–4-methylbenzoic acid (5FU–MBA), C4H3FN2O2·C8H8O2, (I), 5-fluorouracil–3-nitrobenzoic (5FU–NBA), C4H3FN2O2·C7H5NO4, (II), have been prepared characterized by single-crystal X-ray diffraction. In MBA molecules form carboxylic dimers [R22(8) homosynthon]. Similarly, 5FU types base pair via N—H⋯O hydrogen bonds interacts group NBA O—H⋯O bonds, generating R22(8) ring motif (heterosynthon). Furthermore, pairs homosynthon] bonds. Both crystal structures are stabilized C—H⋯F interactions.
sci-hub.se 参考文章(32)
Samuel Ebenezer, Packianathan Thomas Muthiah, 2-Amino-4,6-dimethyl-pyrimidine-anthranilic acid (1/1). Acta Crystallographica Section E-structure Reports Online. ,vol. 66, ,(2010) , 10.1107/S1600536810003661
Song Li, Jia-Mei Chen, Tong-Bu Lu, Synthon polymorphs of 1 : 1 co-crystal of 5-fluorouracil and 4-hydroxybenzoic acid: their relative stability and solvent polarity dependence of grinding outcomes CrystEngComm. ,vol. 16, pp. 6450- 6458 ,(2014) , 10.1039/C4CE00221K
George M. Sheldrick, Crystal structure refinement with SHELXL Acta Crystallographica Section C-crystal Structure Communications. ,vol. 71, pp. 3- 8 ,(2015) , 10.1107/S2053229614024218
Amit Delori, Mark D Eddleston, William Jones, Cocrystals of 5-fluorouracil CrystEngComm. ,vol. 15, pp. 73- 77 ,(2013) , 10.1039/C2CE26147B
Clare F. Macrae, Ian J. Bruno, James A. Chisholm, Paul R. Edgington, Patrick McCabe, Elna Pidcock, Lucia Rodriguez-Monge, Robin Taylor, Jacco van de Streek, Peter A. Wood, Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures Journal of Applied Crystallography. ,vol. 41, pp. 466- 470 ,(2008) , 10.1107/S0021889807067908
CHARLES HEIDELBERGER, N. K. CHAUDHURI, PETER DANNEBERG, DOROTHY MOOREN, LOIS GRIESBACH, ROBERT DUSCHINSKY, R. J. SCHNITZER, E. PLEVEN, J. SCHEINER, Fluorinated Pyrimidines, A New Class of Tumour-Inhibitory Compounds Nature. ,vol. 179, pp. 663- 666 ,(1957) , 10.1038/179663A0
Yuan Gao, Jing Gao, Ziling Liu, Hongliang Kan, Hui Zu, Wanjin Sun, Jianjun Zhang, Shuai Qian, Coformer selection based on degradation pathway of drugs: a case study of adefovir dipivoxil-saccharin and adefovir dipivoxil-nicotinamide cocrystals. International Journal of Pharmaceutics. ,vol. 438, pp. 327- 335 ,(2012) , 10.1016/J.IJPHARM.2012.09.027
Ashley T. Hulme, Sarah L. Price, Derek A. Tocher, A New Polymorph of 5-Fluorouracil Found Following Computational Crystal Structure Predictions Journal of the American Chemical Society. ,vol. 127, pp. 1116- 1117 ,(2005) , 10.1021/JA044336A
Gautam R. Desiraju, Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis Angewandte Chemie. ,vol. 34, pp. 2311- 2327 ,(1995) , 10.1002/ANIE.199523111
Susan Huan, Richard Pazdur, Amnuay Singhakowinta, Bohumil Samal, Vainutis K. Vaitkevicus, Low-dose continuous infusion 5-fluorouracil. Evaluation in advanced breast carcinoma. Cancer. ,vol. 63, pp. 419- 422 ,(1989) , 10.1002/1097-0142(19890201)63:3<419::AID-CNCR2820630303>3.0.CO;2-Z