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  • Guan, Xiaoshu  (4)
  • 2020-2024  (4)
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  • 2020-2024  (4)
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  • 1
    Online Resource
    Online Resource
    A New Co-Crystal of Synthetic Drug Rosiglitazone with Natural Medicine Berberine: Preparation, Crystal Structures, and Dissolution
    MDPI AG ; 2020
    In:  Molecules Vol. 25, No. 18 ( 2020-09-18), p. 4288-
    Details
    In: Molecules, MDPI AG, Vol. 25, No. 18 ( 2020-09-18), p. 4288-
    Abstract: A co-crystal of rosiglitazone (Rsg) with berberine (Bbr), Rsg-Bbr, was prepared by the solvent evaporation method and characterized. The results showed that the electrostatic attraction existed between the nitrogen anion of rosiglitazone and the quaternary ammonium cation of berberine, and C-H···O hydrogen bonds were formed between Rsg and Bbr. In the crystal structure, rosiglitazone molecules stack into a supramolecular layer through π-π interactions while π-π interactions between berberine cations also result in a similar layer. The co-crystal presented a low moisture adsorption curve in the range of 0−95% relative humidity values at 25 °C. The improved dissolution rate of rosiglitazone in pH = 6.8 buffer solution could be achieved after forming co-crystal.
    Type of Medium: Online Resource
    ISSN: 1420-3049
    URL: Article
    DOI: 10.3390/molecules25184288
    Language: English
    Publisher: MDPI AG
    Publication Date: 2020
    detail.hit.zdb_id: 2008644-1
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  • 2
    Online Resource
    Online Resource
    Multicomponent Crystal of Metformin and Barbital: Design, Crystal Structure Analysis and Characterization
    MDPI AG ; 2021
    In:  Molecules Vol. 26, No. 14 ( 2021-07-20), p. 4377-
    Details
    In: Molecules, MDPI AG, Vol. 26, No. 14 ( 2021-07-20), p. 4377-
    Abstract: The formation of most multicomponent crystals relies on the interaction of hydrogen bonds between the components, so rational crystal design based on the expected hydrogen-bonded supramolecular synthons was employed to establish supramolecular compounds with desirable properties. This theory was put into practice for metformin to participate in more therapeutic fields to search for a fast and simple approach for the screening of candidate crystal co-formers. The prediction of intermolecular synthons facilitated the successful synthesis of a new multicomponent crystal of metformin (Met) and barbital (Bar) through an anion exchange reaction and cooling crystallization method. The single crystal X-ray diffraction analysis demonstrated the hydrogen bond-based ureide/ureide and guanidine/ureide synthons were responsible for the self-assembly of the primary structural motif and extended into infinite supramolecular heterocatemeric structures.
    Type of Medium: Online Resource
    ISSN: 1420-3049
    URL: Article
    DOI: 10.3390/molecules26144377
    Language: English
    Publisher: MDPI AG
    Publication Date: 2021
    detail.hit.zdb_id: 2008644-1
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  • 3
    Online Resource
    Online Resource
    Improving Dissolution and Cytotoxicity by Forming Multidrug Crystals
    MDPI AG ; 2020
    In:  Molecules Vol. 25, No. 6 ( 2020-03-16), p. 1343-
    Details
    In: Molecules, MDPI AG, Vol. 25, No. 6 ( 2020-03-16), p. 1343-
    Abstract: Both rosiglitazone and metformin have effects on blood glucose regulation and the proliferation of liver cancer cells. Combination therapy with these two drugs is common and effective for the treatment of diabetes in the clinic, however, the application of these two drugs is influenced by the poor dissolution of rosiglitazone and the gastrointestinal side-effect of metformin resulting from a high solubility. The formation of a multidrug crystal form (Rsg-Met) by a solvent evaporation method can solve the solubility issue. Crystal structure data and intramolecular hydrogen bonds were detected by X-ray diffraction and infrared spectroscopy. Surprisingly, Rsg-Met shortens the time spent in solubility equilibrium and multiplies the dissolution rate of Rsg. Finally, we found that a low concentration of Rsg-Met enhanced the proliferation inhibition effect on liver cancer cells (HepG2, SK-hep1) compared with rosiglitazone, without affecting the human normal cell line LO2.
    Type of Medium: Online Resource
    ISSN: 1420-3049
    URL: Article
    DOI: 10.3390/molecules25061343
    Language: English
    Publisher: MDPI AG
    Publication Date: 2020
    detail.hit.zdb_id: 2008644-1
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  • 4
    Online Resource
    Online Resource
    A facile method to synthesize vildagliptin
    SAGE Publications ; 2021
    In:  Journal of Chemical Research Vol. 45, No. 3-4 ( 2021-03), p. 305-309
    Details
    In: Journal of Chemical Research, SAGE Publications, Vol. 45, No. 3-4 ( 2021-03), p. 305-309
    Abstract: An efficient and high-yielding synthetic method for the preparation of vildagliptin via four steps is reported. The process starts from L-proline and involves a successful reaction with chloroacetyl chloride in tetrahydrofuran to afford ( S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid, followed by a reaction with acetonitrile in the presence of sulfuric acid to give ( S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile. This is then reacted with 3-aminoadamantanol to give vildagliptin. 3-Aminoadamantanol is prepared from 1-aminoadamantane hydrochloride via oxidation with sulfuric acid/nitric acid and boric acid as the catalyst followed by ethanol extraction. The overall yield is 95%.
    Type of Medium: Online Resource
    ISSN: 1747-5198 , 2047-6507
    URL: Article
    DOI: 10.1177/1747519820967123
    Language: English
    Publisher: SAGE Publications
    Publication Date: 2021
    detail.hit.zdb_id: 3010810-X
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