Inclusion of triphenylmethane derivatives by crown and linear O-containing molecules :  selective interactions and crystal structures

Fonarı, Marina S.; Simonov, Yurii A.; Wang, Wen-Jwu; Tang, Shang-Wei; Ganin, E. V.

doi:10.1039/b810076d

Cited by 7 publications

(3 citation statements)

References 43 publications

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“…Regarding ctc-II (Figure 6a), this synthon is more anticipated, since, for example, it has been described in some solvates (such as BOKHIU, BOKHOA, BOKHUG, BOK-JAO), 43 a clathrate (WOPCIO), 44 and some monocomponent structures (such as KUVFIR 45 or NIGNEY 46 ).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Co-crystal of Tramadol Hydrochloride–Celecoxib (ctc): A Novel API–API Co-crystal for the Treatment of Pain

Almansa

MercÃ

Tesson³

et al. 2017

Crystal Growth & Design

126

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We have identified a co-crystal of tramadol hydrochloride−celecoxib (ctc; E-58425/MR308), a novel active pharmaceutical ingredient (API)−API co-crystal formed by an intrinsic 1:1 molecular ratio of rac-tramadol•HCl and celecoxib, which displays favorable physicochemical and dissolution profiles. Adequate treatment of pain represents an unmet medical need that is often addressed via combination therapy. API−API co-crystals represent a new approach with potential to improve physicochemical properties, bioavailability, stability, or formulation capacity, which may translate into optimized pharmacokinetic profiles and clinical benefits compared with individual APIs or their combination. ctc showed a well-defined differential scanning calorimetry profile, and its single-crystal X-ray diffraction structure demonstrated a supramolecular 3D network in which the two active enantiomers of tramadol and celecoxib are linked via hydrogen bonding and chloride ions. Oversaturation studies indicated that the saturation effect for highly insoluble celecoxib occurred at a higher concentration in ctc than in celecoxib alone. Comparative intrinsic dissolution rate studies showed that the release of celecoxib was faster, and the release of tramadol was slower, from ctc than from the individual APIs, predicting an improved pharmacokinetic behavior for ctc. Together with findings from preclinical studies, these data support the clinical development of ctc for the treatment of pain.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Co-crystal of Tramadol Hydrochloride–Celecoxib (ctc): A Novel API–API Co-crystal for the Treatment of Pain

Almansa

MercÃ

Tesson³

et al. 2017

Crystal Growth & Design

126

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“…In this structure, hydrogen atoms on the phenyl group of 1 were placed using the residual peaks of the electron density to evaluate the intermolecular CH···π interaction ( vide infra ), while the others were placed at calculated positions. In the molecular structure of 1 , the C1–O1 bond length (1.408(5) Å) is similar to those of triphenylmethanol (1.414(2)–1.448(5) Å, average 1.437(8) Å), whose hydroxy groups engage in hydrogen bonds in the crystalline state similar to those of 1 ( vide infra ). − The C1 atom adopts a tetrahedral geometry, as is evident from the mean bond angle around C1 (109.5(3)°, 104.6(3)–115.1(3)°), which is identical to the H–C–H angle of methane (109.5°). The EtOAc solvate molecule engages in an N1–H1···O2 hydrogen bond with one of the benzimidazole rings in 1 .…”

Section: Resultsmentioning

confidence: 75%

Water-Tolerant Hydrogen-Bonded Organic Framework Based on Phenylbis(benzimidazol-2-yl)methanol: Synthesis, Structural Characterization, and Organic-Vapor-Adsorption Properties

Ohta,

Hatakeyama,

Fujita

et al. 2024

Crystal Growth & Design

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Imidazole derivatives are promising building blocks for the construction of hydrogen-bonded organic frameworks (HOFs); however, imidazole-based HOFs are still much less explored than HOFs based on more prominent building blocks, such as carboxy-group-containing organic compounds and 2,4-diaminotriazine moieties. Here, we report a HOF based on phenylbis-(benzimidazol-2-yl)methanol (1). The porous framework of the 1-based HOF is mainly constructed by intermolecular O−H•••N and N−H•••N hydrogen bonds, with ethyl acetate (EtOAc) solvate molecules occupying the pores. The EtOAc guest molecules can be removed by heating (100 °C) the as-synthesized 1-based HOF under reduced pressure or by treating it with supercritical carbon dioxide via a single-crystal-to-single-crystal transformation involving a large framework motion. The desolvated HOF can adsorb the vapors of EtOAc, 2-pentanone, 3pentanone, 2-butanone, diethyl ether, and diethylamine even under high-humidity conditions, which renders the 1-based HOF a promising material for organic-vapor adsorption in the context of industrial applications.

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“…2,3 In other respects, the basic compound triphenylmethanol has been shown to selectively enclathrate methanol and DMSO in its crystal lattice 4 while more bulkily substituted triphenylmethanol derivatives and analogous triarylmethanols demonstrate corresponding inclusion formation with other guest solvents. 5 Conversely, triphenylmethane derivatives as the guest were found to be inclusion-complexed with crown compounds 6,7 and, as a further subject, the packing modes of trityl alcohols have been studied in dependency of specific para substitution involving different halogen atoms. 8,9 In all these latter structures, O-H⋯π 10 and halogen⋯π 11,12 interactions have proven to dominate the crystal lattices while conventional O-H⋯O hydrogen bonding 13 is prevented from steric reason.…”

Section: Introductionmentioning

confidence: 99%

Aspects of crystal engineering arising from packing behavior of functional mono para-substituted trityl compounds

et al. 2015

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Four trityl compounds differing both in the functional group (OH, OMe, NH 2 ) at the specific trityl carbon and a para substituent, being bromine or phenyl at one of the phenyl groups, have been prepared and structurally studied by means of single crystal X-ray diffraction and making use of Hirshfeld surface analysis.Compared to the structures of corresponding prototypes and analogues, specific interaction modes and packing motifs including cluster aggregates as well as non-cluster type structures depending on the substitution and involving polymorphism were found, opening potential trend prediction with reference to crystal engineering being useful in this compound class. CrystEngCommThis journal is

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Inclusion of triphenylmethane derivatives by crown and linear O-containing molecules : selective interactions and crystal structures

Cited by 7 publications

References 43 publications

Co-crystal of Tramadol Hydrochloride–Celecoxib (ctc): A Novel API–API Co-crystal for the Treatment of Pain

Co-crystal of Tramadol Hydrochloride–Celecoxib (ctc): A Novel API–API Co-crystal for the Treatment of Pain

Water-Tolerant Hydrogen-Bonded Organic Framework Based on Phenylbis(benzimidazol-2-yl)methanol: Synthesis, Structural Characterization, and Organic-Vapor-Adsorption Properties

Aspects of crystal engineering arising from packing behavior of functional mono para-substituted trityl compounds

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