genistein tetrabutylammonium salt

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: genistein tetrabutylammonium salt
• 英文别名: 7-O-genistein tetra-butylammonium salt；tetra n-butylammonium salt of genistein；7-Hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-5-olate;tetrabutylazanium
• 化学式: C₁₅H₉O₅*C₁₆H₃₆N
• 分子量: 511.702
• InChiKey: TUMNSSFEYRLNCL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.95
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  genistein tetrabutylammonium salt 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(3-(4-(1-(2-((5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)ethyl)-1H-1,2,3-triazol-4-yl)benzyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile
  参考文献：
  名称：

  乙内酰脲衍生的抗雄激素-染料木黄酮缀合物的抗增殖活性的设计、合成和评估。

  摘要：

  雄激素受体 (AR) 信号传导对于所有形式的前列腺癌 (PCa) 的生存至关重要。为了研究同时抑制和消除 AR 对 PCa 细胞活力的影响，我们设计、合成并表征了双功能药物的生物活性，其中结合了抗雄激素和金雀异黄素的独立癌症杀伤特性，以及 AR 下调作用单一分子模板内的金雀异黄素。我们观察到，相对于作为单一药剂或它们的组合的抗雄激素和金雀异黄素结构单元，代表性缀合物9b对 LNCaP 和 DU145 细胞的细胞毒性要大得多。此外，相对于金雀异黄素，缀合物9b更有效地下调细胞 AR 蛋白水平并诱导 S 期细胞周期停滞。这些缀合物的有前途的生物活性值得进一步研究。

  DOI：

  10.1016/j.bmc.2018.01.009
• 作为产物：
  描述：

  染料木素 、 四丁基氢氧化铵 以 甲醇 、 水 为溶剂， 以89%的产率得到genistein tetrabutylammonium salt
  参考文献：
  名称：

  X-ray and 13C CP MAS investigations of structure of two genistein derivatives

  摘要：

  Structural and spectroscopic properties of two distinctly different derivatives of genistein (1), ionic and covalent, engaging the most acidic of its three phenolic functions, have been investigated. Both the 7-O-silyl ether (2), and ammonium salt (3), are stable solids, considered to be useful intermediates for achieving further chemical transformations in a manner securing highly regioselective outcome. It turned out that these two molecules contain genistein structural fragment involved in many intra- and intermolecular hydrogen bonds. In the case of 2, some infinite chains of coupled intra- and intermolecular hydrogen bonds are formed supported by hydrogen bonding to water molecules. In the structure of 3, a helical arrangement of genistein moieties is formed with the cations kept in voids. Single crystal X-ray diffraction shows that the aromatic ring B in both structures is rotated with respect to the AC fused rings of the chromenone moiety by ca. 36degrees (2) and 50degrees (3). Both new compounds crystallise as monohydrates. The number of peaks observed in the solid-state C-13 spectra of 2 and 3 corresponds to the number of magnetically non-equivalent carbons and it is in satisfactory agreement with the X-ray crystal structures of both genistein derivatives. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2004.03.015

文献信息

• Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein
  作者：Wieslaw Szeja、Grzegorz Grynkiewicz、Tadeusz Bieg、Piotr Swierk、Anna Byczek、Katarzyna Papaj、Radosław Kitel、Aleksandra Rusin

  DOI：10.3390/molecules19067072

  日期：——

  A series of glycoconjugates, derivatives of genistein containing a C-glycosylated carbohydrate moiety, were synthesized and their anticancer activity was tested in vitro in the human cell lines HCT 116 and DU 145. The target compounds 15–17 were synthesized by treating ω-bromoalkyl C-glycosides derived from L-rhamnal (1) with a tetrabutylammonium salt of genistein. The new, metabolically stable analogs of previously studied O-glycosidic genistein derivatives inhibited proliferation of cancer cell lines through inhibition of the cell cycle.

  一系列糖缀合物，包含C-糖基化碳水化合物部分的染料木素衍生物，被合成了并在体外对人体细胞系HCT 116和DU 145进行了抗癌活性测试。目标化合物15-17通过用四丁基铵盐处理来自L-鼠李醛（1）的ω-溴烷基C-糖苷来合成。与先前研究的O-糖基化染料木素衍生物相比，这些新的、代谢稳定的类似物通过抑制细胞周期来抑制癌细胞系的增殖。
• Synthetic conjugates of genistein affecting proliferation and mitosis of cancer cells
  作者：Aleksandra Rusin、Jadwiga Zawisza-Puchałka、Katarzyna Kujawa、Agnieszka Gogler-Pigłowska、Joanna Wietrzyk、Marta Świtalska、Magdalena Głowala-Kosińska、Aleksandra Gruca、Wiesław Szeja、Zdzisław Krawczyk、Grzegorz Grynkiewicz

  DOI：10.1016/j.bmc.2010.11.024

  日期：2011.1

  Antiproliferative activity of several genistein derivatives was tested in cancer cell lines in vitro. The most potent derivative, Ram-3 inhibited the cell cycle, interacted with mitotic spindles and caused apoptotic cell death. Neither genistein nor the sugar alone were able to influence the mitotic spindle organization. Our results indicate, that conjugation of genistein with certain sugars may render

  本文描述了染料木黄酮（1）和不饱和吡喃糖苷的结合物的合成及其抗增殖活性。通过两步合成获得将染料木黄酮通过烷基链与糖部分连接的构建体：第一步，染料木黄酮在位置7被转化为带有ω-羟烷基取代基的中间体，该中间体含有两个，三个或五个碳原子。而第二步则涉及利用Feryl进行Ferrier糖基化反应。在体外在癌细胞系中测试了几种染料木黄酮衍生物的抗增殖活性。最有效的衍生物Ram-3抑制细胞周期，与有丝分裂纺锤体相互作用，并导致凋亡性细胞死亡。金雀异黄素和糖都不能影响有丝分裂纺锤体的组织。我们的结果表明，金雀异黄素与某些糖的结合可能使衍生物与新的分子靶标相互作用。
• Goj, Katarzyna; Rusin, Aleksandra; Szeja, Wiesław, Acta poloniae pharmaceutica, 2012, vol. 69, # 6, p. 1239 - 1247
  作者：Goj, Katarzyna、Rusin, Aleksandra、Szeja, Wiesław、Kitel, Radosław、Komor, Roman、Grynkiewicz, Grzegorz

  DOI：——

  日期：——
• X-ray and 13C CP MAS investigations of structure of two genistein derivatives
  作者：Grzegorz Grynkiewicz、Oliwia Zegrocka-Stendel、Wiesław Pucko、Jan Ramza、Anna Kościelecka、Wacław Kołodziejski、Krzysztof Woźniak

  DOI：10.1016/j.molstruc.2004.03.015

  日期：2004.6

  Structural and spectroscopic properties of two distinctly different derivatives of genistein (1), ionic and covalent, engaging the most acidic of its three phenolic functions, have been investigated. Both the 7-O-silyl ether (2), and ammonium salt (3), are stable solids, considered to be useful intermediates for achieving further chemical transformations in a manner securing highly regioselective outcome. It turned out that these two molecules contain genistein structural fragment involved in many intra- and intermolecular hydrogen bonds. In the case of 2, some infinite chains of coupled intra- and intermolecular hydrogen bonds are formed supported by hydrogen bonding to water molecules. In the structure of 3, a helical arrangement of genistein moieties is formed with the cations kept in voids. Single crystal X-ray diffraction shows that the aromatic ring B in both structures is rotated with respect to the AC fused rings of the chromenone moiety by ca. 36degrees (2) and 50degrees (3). Both new compounds crystallise as monohydrates. The number of peaks observed in the solid-state C-13 spectra of 2 and 3 corresponds to the number of magnetically non-equivalent carbons and it is in satisfactory agreement with the X-ray crystal structures of both genistein derivatives. (C) 2004 Elsevier B.V. All rights reserved.
• Design, synthesis, and evaluation of the antiproliferative activity of hydantoin-derived antiandrogen-genistein conjugates
  作者：Alex George、Idris Raji、Bekir Cinar、Omer Kucuk、Adegboyega K. Oyelere

  DOI：10.1016/j.bmc.2018.01.009

  日期：2018.5

  Androgen receptor (AR) signaling is vital to the viability of all forms of prostate cancer (PCa). With the goal of investigating the effect of simultaneous inhibition and depletion of AR on viability of PCa cells, we designed, synthesized and characterized the bioactivities of bifunctional agents which incorporate the independent cancer killing properties of an antiandrogen and genistein, and the AR

  雄激素受体 (AR) 信号传导对于所有形式的前列腺癌 (PCa) 的生存至关重要。为了研究同时抑制和消除 AR 对 PCa 细胞活力的影响，我们设计、合成并表征了双功能药物的生物活性，其中结合了抗雄激素和金雀异黄素的独立癌症杀伤特性，以及 AR 下调作用单一分子模板内的金雀异黄素。我们观察到，相对于作为单一药剂或它们的组合的抗雄激素和金雀异黄素结构单元，代表性缀合物9b对 LNCaP 和 DU145 细胞的细胞毒性要大得多。此外，相对于金雀异黄素，缀合物9b更有效地下调细胞 AR 蛋白水平并诱导 S 期细胞周期停滞。这些缀合物的有前途的生物活性值得进一步研究。