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Cocrystals and a Salt of the Bioactive Flavonoid: Naringenin

机译：Cocrystals和生物活性类黄酮的盐：Naringenin

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摘要

Cocrystallization studies on naringenin with 27 coformers led to the formation of five new solid forms: piperazinium salt and four cocrystals with the coformers flavone, 4-hydroxypyridine, anthranilamide, and 4,4'-bipyridine. Structural characterization revealed that the hydrogen-bonded head-to-tail dimer motif in naringenin is maintained only in the cocrystal with flavone. All four neutral cocrystals maintain the S(6) O-H center dot center dot center dot O=C intramolecular hydrogen bond seen in naringenin with this carbonyl oxygen atom bifurcated. The piperazinium salt is the only structure in which the ether oxygen is involved in hydrogen bonding. Some of the structures display disorder in the chiral center of naringenin, making them anomalous racemic solid solutions. The solubility study revealed that the salt formation has significantly enhanced the solubility of naringenin, for example, the piperazinium salt has enhanced solubility of more than 3000 times that of the neutral parent compound.
机译：具有27个Coformers的柚皮素的共晶研究导致形成五种新的固体形式：哌嗪鎓盐和四个碳酸吡啶，4-羟基吡啶，壬酰胺和4,4'-双嘧啶的哌嗪盐。结构表征揭示了纳宁纳蛋白中的氢键合的头尾二聚体基质仅在用黄酮中维持在Cocrystal中。所有四个中性的Cocrystals维持S（6）O-H中心点中心点中心点o = C在Naringenin中看到的分子内氢键，并分叉该羰基氧原子。哌嗪鎓盐是乙醚氧涉及氢键的唯一结构。一些结构显示在柚皮素手性中心的紊乱，使其成为异常的外消旋固溶解决方案。溶解度研究表明，盐形成已显着增强了柚皮蛋白的溶解度，例如，哌嗪鎓盐具有增强的中性母体化合物的3000倍以上的溶解度。

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  • 来源
    《Crystal growth & design》 |2018年第8期|共7页
  • 作者

    Khandavilli U. B. Rao; Skaepova Eliska; Sinha Abhijeet S.; Bhogala Balakrishna R.; Maguire Nuala M.; Maguire Anita R.; Lawrence Simon E.;

  • 作者单位

    Univ Coll Cork Synth &

    Solid State Pharmaceut Ctr Analyt &

    Biol Chem Res Facil Sch Chem Cork Ireland;

    Univ Coll Cork Synth &

    Solid State Pharmaceut Ctr Analyt &

    Biol Chem Res Facil Sch Chem Cork Ireland;

    Univ Coll Cork Synth &

    Solid State Pharmaceut Ctr Analyt &

    Biol Chem Res Facil Sch Chem Cork Ireland;

    Univ Coll Cork Synth &

    Solid State Pharmaceut Ctr Analyt &

    Biol Chem Res Facil Sch Chem Cork Ireland;

    Univ Coll Cork Synth &

    Solid State Pharmaceut Ctr Analyt &

    Biol Chem Res Facil Sch Chem Cork Ireland;

    Univ Coll Cork Synth &

    Solid State Pharmaceut Ctr Analyt &

    Biol Chem Res Facil Sch Chem Cork Ireland;

    Univ Coll Cork Synth &

    Solid State Pharmaceut Ctr Analyt &

    Biol Chem Res Facil Sch Chem Cork Ireland;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 晶体学;
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