2-Carboxy-5-(trifluoromethyl)phenyl acetate

Zhang, Ren; Wang, Dan; Ma, Chunmei; Li, Zhenjiang

doi:10.1107/s1600536807055171

Cited by 4 publications

(6 citation statements)

References 3 publications

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“…This is the major difference when compared to the free acid HTrf, wherein the carboxylic group is nearly coplanar with the aromatic ring (5.758). [23] The pyridine ring of PhPy is twisted 51. These CuÀCu distances are of 5.888 (7) .…”

Section: Crystal Structure Elucidationmentioning

confidence: 99%

Green Synthesis of Copper Triflusalate and Pyridine Adducts

et al. 2016

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Conventional organic solvents are the preferred media to prepare and crystallize metallorganic materials, since the wide diversity of organic solvents allows the control of solubility parameters and precipitation kinetics. However, they are the largest waste input in fine chemical synthesis; and moreover, in the processing of materials with ester containing groups, which have a significant tendency to hydrolysis, the use of organic solvents can be too aggressive to keep the structure of labile molecules. In this context, milder methods to prepare crystalline metallorganic derivatives of triflusal (HTrf), a drug bearing an ester group, are here described. HTrf molecule itself and its derivatives have important applications in the pharmaceutical industry. In this work, copper triflusalate complexes and derived pyridine adducts are prepared via an environmentally friendly supercritical CO2 method, preserving the ester group from hydrolysis. For comparison, some intricate conventional solvent liquid methods are also envisaged. Products are fully characterized in regard of composition, structure and magnetic properties.

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Section: Crystal Structure Elucidationmentioning

confidence: 99%

Green Synthesis of Copper Triflusalate and Pyridine Adducts

et al. 2016

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“…One of the problems with the in-silico seeding approach is that the data sets available with suitable structures have been limited. However, from a recent systematic, experimental study on the crystal structures of aspirin (see Figure ) and some of its derivatives, − and including other published structures of similar molecules, − a data set of 21 crystal structures from 18 different molecules has been compiled. The polymorphism of aspirin has been investigated in an early computational study .…”

Section: Introductionmentioning

confidence: 99%

“In-Silico Seeding”: Isostructurality and Pseudoisostructurality in a Family of Aspirin Derivatives

Kendrick

Montis

Hursthouse

et al. 2013

Crystal Growth & Design

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Novel crystal packings of the aspirin molecule and 17 molecules that are related to aspirin by substitution are studied using a computational approach. The packings are created by taking a crystal structure for which the crystal packing and molecular geometry have been determined experimentally and replacing the native molecule with a different one. The resulting crystal structures are optimized using molecular mechanics, followed by a quantum mechanical method based on density functional theory and including a correction for dispersive interactions. There are 21 known, experimental, crystal structures for the molecules considered, some of which are polymorphic. For any given molecule, the lowest, calculated lattice energy is always found to be that of a crystal structure which corresponds to experiment. For the three polymorphic molecules, the second lowest lattice energy is also found to correspond to an experimental structure. The agreement between the observation of a particular packing and its low rank in the list of possible packings is evidence of the accuracy of the method for calculating the lattice energy. Further analysis of the results shows patterns reflecting the underlying supramolecular constructs that are common to the different packings of these molecules. This leads to some speculation as to the possibilities of finding new polymorphs for some of these molecules.

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“…Crystal structure of triflusal has been reported by Zhang et al 13 In the crystal structure, the asymmetric unit contains two symmetry independent molecules and features an acidacid dimer synthon involving both the symmetry independent molecules. The dimer units self-assemble in the crystal structure via several C-H⋯F interactions.…”

Section: Resultsmentioning

confidence: 96%

Novel pharmaceutical cocrystals of triflusal: crystal engineering and physicochemical characterization

et al. 2015

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A platelet aggregation inhibitor, triflusal, is practically insoluble in water and rapidly converts to 2-hydroxy-4-trifluoromethylbenzoic acid (HTB) in physiological systems. Six cocrystals of triflusal were discovered from a cocrystal screening with pharmaceutically acceptable coformers, namely, benzamide, isonicotinamide, picolinamide, propionamide, urea, and valpromide, in an attempt to find stable solid forms of triflusal. The choice of coformers was based on a crystal engineering strategy relying on the carboxylic acid group of the triflusal and the most prevalent supramolecular interactions that it can form with complementary functional groups. Crystal structure analysis revealed that all the cocrystals feature heterosynthons involving carboxylic acid group of triflusal and pyridine/amide group of the coformers. Except the cocrystals with propionamide and valpromide, all the cocrystals were found to be stable at accelerated storage condition (40 °C, 75% relative humidity). Under slurry conditions, cocrystals with benzamide, picolinamide, and valpromide were found stable, but the remaining cocrystals undergo dissociation and degration of triflusal to HTB. As triflusal is known to undergo degradation in the presence of pharmaceutical excipients, the stable triflusal cocrystals reported herein may serve as promising candidates for development of novel triflusal drug formulations.

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2-Carboxy-5-(trifluoromethyl)phenyl acetate

Cited by 4 publications

References 3 publications

Green Synthesis of Copper Triflusalate and Pyridine Adducts

Green Synthesis of Copper Triflusalate and Pyridine Adducts

“In-Silico Seeding”: Isostructurality and Pseudoisostructurality in a Family of Aspirin Derivatives

Novel pharmaceutical cocrystals of triflusal: crystal engineering and physicochemical characterization

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