Synthetic Strategies toward Higher Cocrystals of Some Resorcinols

Crystal Growth & Design, Год журнала: 2022, Номер 22(12), С. 7578 - 7589

Опубликована: Ноя. 22, 2022

Higher cocrystal synthesis depends on precise strategic approaches. A total of 32 stoichiometric ternary and quaternary cocrystals based resorcinol derivatives were achieved using structural inequivalence shape–size mimicry approaches are reported here. Along with 28 binary precursors that also obtained, these 60 serve to generalize synthetic strategies toward ends. number large synthon Aufbau modules (LSAMs) designed depending the substitution pattern in resorcinol. The LSAMs from 5-substituted found be useful designing higher cocrystals. construction a without "special" compound 2,3,5,6-tetramethylpyrazine has been finally secured.

Язык: Английский

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N-1,3-thiazole-2-ylacetamide: An Efficient Novel Cocrystal Former with Carboxylic Acids

Journal of Molecular Structure, Год журнала: 2025, Номер unknown, С. 142706 - 142706

Опубликована: Май 1, 2025

Язык: Английский

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Synthesis, Crystal Growth, Structural Characterization, Supramolecular Chemistry, and Theoretical Calculations of Methylenium Salts of Benzenesulfonates

ChemistrySelect, Год журнала: 2024, Номер 9(17)

Опубликована: Апрель 30, 2024

Abstract The current investigation describes the synthesis of four novel methylene blue (MB) salts benzene sulfonate derivatives, featuring bulky anionic groups. process involves treating chloride salt MB with sodium 4‐aminobenzene sulfonate, 4‐styrenebenzene 3,7‐naphthalene disulfonate, and anthraquinone‐1,5‐naphthalene disulfonate to substitute ion benzoate anion in MB‐chloride. includes quaternizing MB‐chloride corresponding minimal aqueous solvent promote precipitation. resultant precipitates were subsequently dissolved an appropriate enable crystallization ultimate product. dissolution occurs either at ambient temperature or heat. crystals characterized using various analytical techniques like UV‐visible, FT‐IR spectroscopy, TGA, single crystal X‐ray diffraction powder analysis. UV‐visible spectroscopic results, frontier molecular orbital, density states, electrostatic potentials, HOMO‐LUMO energy gaps estimated by DFT. Structural analysis revealed that supramolecular structure compounds achieved stabilization through interactions, a diverse range both conventional non‐conventional hydrogen bonds, π–π stacking other short‐range interactions. delves into intricate details offers thorough discussion fundamental principles contribute formation structures.

Язык: Английский

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Crystal engineering of ionic cocrystals comprising Na/K salts of hesperetin with hesperetin molecules and solubility modulation

IUCrJ, Год журнала: 2023, Номер 10(3), С. 329 - 340

Опубликована: Март 27, 2023

Hesperetin (HES) is a weakly acidic flavonoid of topical interest owing to its antiviral properties. Despite the presence HES in many dietary supplements, bioavailability hindered by poor aqueous solubility (1.35 µg ml −1 ) and rapid first-pass metabolism. Cocrystallization has evolved as promising approach generate novel crystal forms biologically active compounds enhance physicochemical properties without covalent modification. In this work, engineering principles were employed prepare characterize various HES. Specifically, two salts six new ionic cocrystals (ICCs) involving sodium or potassium studied using single-crystal X-ray diffraction (SCXRD) powder thermal measurements. Structures seven crystalline elucidated SCXRD, which revealed families isostructural ICCs terms their packing confirmed phenol...phenolate (PhOH...PhO − supramolecular heterosynthons. Diverse conformations observed amongst these structures, including unfolded folded (previously unreported) conformations. One ICC, with salt (NESNAH), was scalable gram scale found be stable after accelerated stability testing (exposure elevated heat humidity). HESNAH reached C max 10 min PBS buffer 6.8 compared 240 pure addition, relative 5.5 times greater, offering possibility improved bioavailability.

Язык: Английский

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Crystal Engineering of Ionic Cocrystals Sustained by Azolium···Azole Heterosynthons

Pharmaceutics, Год журнала: 2022, Номер 14(11), С. 2321 - 2321

Опубликована: Окт. 28, 2022

Crystal engineering of multi-component molecular crystals, cocrystals, is a subject growing interest, thanks in part to the potential utility pharmaceutical cocrystals as drug substances with improved properties. Whereas (MCCs) are quite well studied from design perspective, ionic (ICCs) remain relatively underexplored despite there being several recently FDA-approved products based upon ICCs. Successful cocrystal strategies typically depend on strong and directional noncovalent interactions between coformers, exemplified by hydrogen bonds. Understanding hierarchy such key successful outcomes design. We herein address crystal ICCs comprising azole functional groups, particularly imidazoles triazoles, which commonly encountered biologically active molecules. Specifically, azoles were for their propensity serve coformers organic (trifluoroacetic acid p-toluenesulfonic acid) inorganic (hydrochloric acid, hydrobromic nitric acids gain insight into NH+···N (azolium-azole) supramolecular heterosynthons. Accordingly, we combined data mining Cambridge Structural Database (CSD) structural characterization 16 new (11 imidazoles, 4 one imidazole-triazole). Analysis 66 relevant hits archived CSD revealed that synthons identical rings (A+B-A) much more encountered, 71, than different (A+B-C), 11. The average distance found reported 2.697(3) Å binding energy calculations suggested bond strengths range 31-46 kJ mol-1. azolium-triazole ICC (A+B-C) was obtained via mechanochemistry differed other no bonding. That CNC angles 1,2,4-triazoles sensitive protonation, cationic forms having larger (approximately 4.4 degrees) values comparable neutral rings, used parameter distinguish protonated rings. Our results indicate azolium-azole heterosynthons viable targets, has implications development

Язык: Английский

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Conformational Trimorphism in an Ionic Cocrystal of Hesperetin

Crystal Growth & Design, Год журнала: 2022, Номер 22(11), С. 6390 - 6397

Опубликована: Окт. 4, 2022

We report the existence of conformational polymorphism in an ionic cocrystal (ICC) nutraceutical compound hesperetin (HES) which its tetraethylammonium (TEA+) salt serves as a coformer. Three polymorphs, HESTEA-α, HESTEA-β and HESTEA-γ, were characterized by single-crystal X-ray diffraction (SCXRD). Each polymorph was found to be sustained phenol···phenolate supramolecular heterosynthons that self-assemble with phenol···phenol homosynthons into C32(7) H-bonded motifs. Conformational variability HES moieties different relative orientations motifs resulted distinct crystal packing patterns: HESTEA-α exhibit sheets; HESTEA-γ is bilayers tapes. All three polymorphs stable upon exposure humidity under accelerated stability conditions for 2 weeks. Under competitive slurry conditions, observed transform β or γ forms. Solvent selection impacted relationship between (favored EtOH) MeOH). A mixture forms present following H2O slurry.

Язык: Английский

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Technical and Formulation Aspects of Pharmaceutical Co‐Crystallization: A Systematic Review

ChemistrySelect, Год журнала: 2022, Номер 7(37)

Опубликована: Окт. 6, 2022

Abstract Crystal engineering provides a unique approach to modulating the physicochemical properties of forming active drug molecules so nowadays pharmaceutical companies and researchers have shown interest in designing building cocrystals. Creating new crystalline solid structures with altered such as solubility, bioavailability, tabletability, melting point, stability, on. The intermolecular interactions crystal lattice are used investigate these properties. Numbers methods for crystallizing summarised analyzed, pointing advantages disadvantages that been highlighted literature. This literature review discusses detail different types cocrystals, their mechanisms, applications characterization. main purpose this article is look at what has changed field last ten years show could be learned from better research on cocrystal formation how it can used.

Язык: Английский

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Polymorphs, ionic cocrystal and inclusion complex of N-amino-1,8-naphthalimide

CrystEngComm, Год журнала: 2023, Номер 25(13), С. 1928 - 1940

Опубликована: Янв. 1, 2023

The importance of symmetry non-equivalent molecules in the unit cell and enhancement content a component assemblies are demonstrated.

Язык: Английский

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Novel lithium ionic cocrystals with benzoic acid derivatives and L-proline: Synthesis, X-ray structures, IR spectrums, DSC analysis, and water solubility

Journal of Molecular Structure, Год журнала: 2024, Номер 1315, С. 138795 - 138795

Опубликована: Май 29, 2024

Язык: Английский

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Host–Guest Complexes of p-Sulfonato-calix[4]arene and Benzamidine: A Matter of Counterion and Aging in the Mother Liquor

Crystal Growth & Design, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 24, 2024

Язык: Английский

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