4',5,7-Triacetoxyisoflavone | 5995-97-1

• 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: 4',5,7-Triacetoxyisoflavone
• 英文别名: 7-acetyloxy-3-(4-acetyloxyphenyl)-4-oxochromen-5-yl acetate；4',5,7-triacetoxyisoflavanone；4',5,7-tri-O-acetylgenistein；4',5,7-O-triacetylgenistein；genistein triacetate；triacetylgenistein；5-(Acetyloxy)-3-[4-(acetyloxy)phenyl]-4-oxo-4H-chromen-7-yl acetate；[4-(5,7-diacetyloxy-4-oxochromen-3-yl)phenyl] acetate
• CAS: 5995-97-1
• 化学式: C₂₁H₁₆O₈
• 分子量: 396.353
• InChiKey: YFPWPHUQAVBEHF-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于二氯甲烷、二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  4',5,7-Triacetoxyisoflavone 在 氢氧化钾 、 potassium carbonate 、 丙酮 作用下， 生成 异樱黄素
  参考文献：
  名称：

  Heitz; Mentzer, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 3575

  摘要：

  DOI：
• 作为产物：
  描述：

  槐角苷 在 水 作用下， 生成 4',5,7-Triacetoxyisoflavone
  参考文献：
  名称：

  Study of sophoricoside derivatives with the aid of lanthanoid shift reagents

  摘要：

  DOI：

  10.1007/bf01372607

文献信息

• An Efficient Method for the Glycosylation of Isoflavones
  作者：Nawaf Al-Maharik、Nigel P. Botting

  DOI：10.1002/ejoc.200800803

  日期：2008.11

  A new efficient, high-yielding glycosylation procedure is described for isoflavones, which employs 2,2,2-trifluoro-N-(p-methoxyphenyl)acetamidates as the glycosyl donors. This methodology was used to prepare the 7-O-glycosides of the three main isoflavones, daidzein, genistein and glycitein. The isoflavones were protected with hexanoyl groups which improved their solubility in organic solvents and

  异黄酮植物雌激素因其正面和负面的健康益处而受到当前的关注。然而，关于它们的吸收、代谢和生物利用度，仍有许多悬而未决的问题。该领域的研究需要获取异黄酮 7-O-葡萄糖苷（在植物中发现的形式）和 7-O-葡萄糖醛酸苷（它们是重要的哺乳动物代谢物）的样本。描述了一种新的高效、高产的异黄酮糖基化程序，它采用 2,2,2-三氟-N-（对甲氧基苯基）乙酰胺作为糖基供体。该方法用于制备三种主要异黄酮、黄豆苷元、染料木黄酮和黄豆黄素的 7-O-糖苷。异黄酮用己酰基保护，这提高了它们在有机溶剂中的溶解度并提高了反应效率。然后采用相同的方法合成类似的 7-O-葡糖苷酸。新的合成将为进一步的生物学研究提供大量这些化合物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Production of isoflavone derivatives
  申请人：Heaton Andrew

  公开号：US20050143588A1

  公开（公告）日：2005-06-30

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  描述了异黄酮氢化的方法，可以获得可操作数量的异黄烷-4-醇、异黄烯和异黄烷。在使用药用可接受的试剂和溶剂时，可以高纯度地获得异黄酮衍生物，并且产率接近定量。
• Dietary Phytoestrogens and Their Synthetic Structural Analogues as Calcium Channel Blockers in Human Platelets
  作者：Yuliya Dobrydneva、Roy L. Williams、Gary Z. Morris、Peter F. Blackmore

  DOI：10.1097/00005344-200209000-00009

  日期：2002.9

  Phytoestrogens have been shown to inhibit platelet activation by blocking platelet calcium channels. This study examined the effect of several synthetic derivatives of trans-resveratrol, genistein, and daidzein on plateletfree intracellular calcium ([Ca2+]i) elevation in thrombin-activated platelets and the possible mechanisms of this inhibitory effect. Studies were conducted on fresh human platelets from healthy volunteers. The fluorescent dye fura-2 was used to monitor [Ca2+]i in platelets. At 10 μM trans-resveratrol, triacetyl-trans-resveratrol, and trimethoxy-trans-resveratrol produced, respectively, 57 ± 4%, 40 ± 4%, and 21 ± 1% inhibition; genistein, acetylgenistein, and dihydrogenistein produced 51 ± 10%, 26 ± 7%, and 16 ± 2% inhibition, respectively; daidzein and diacetyldaidzein produced 56 ± 5% and 45 ± 10% inhibition of thrombin-induced [Ca2+]i elevation. The inhibitory effect was immediate and appeared to directly affect the calcium influx channels. Phytoestrogen action on [Ca2+]i did not cause alteration in nitric oxide signaling. Tyrosine phosphorylation was not involved in the inhibition of [Ca2+]i elevation by phytoestrogens, because the percent inhibition produced by the tyrosine kinase inhibitor genistein and its inactive analogue daidzein on thrombin-induced and thapsigargin-induced [Ca2+]i elevation was not significantly different for either compound at any concentration tested. Structure–activity relationship studies on this limited set of compounds reveal the requirements for the stilbene pharmacophore for the calcium-blocking activity.

  植物雌激素可通过阻断血小板钙通道抑制血小板活化。本研究考察了几种反式白藜芦醇、染料木素和大豆异黄酮的合成衍生物对凝血酶激活的血小板游离细胞内钙（[Ca2+]i）升高的影响以及这种抑制作用的可能机制。研究以健康志愿者的新鲜人体血小板为对象。使用荧光染料 fura-2 监测血小板中的[Ca2+]i。在 10 μM 的反式-白藜芦醇、三乙酰基-反式-白藜芦醇和三甲氧基-反式-白藜芦醇浓度下，分别产生 57 ± 4%、40 ± 4% 和 21 ± 1% 的抑制作用；染料木素、乙酰染料木素和二氢染料木素分别产生 51 ± 10%、26 ± 7% 和 16 ± 2% 的抑制作用；大豆雌酚和二乙酰大豆雌酚分别产生 56 ± 5% 和 45 ± 10% 的凝血酶诱导的 [Ca2+]i 升高抑制作用。抑制作用是即时的，似乎直接影响了钙离子通道。植物雌激素对[Ca2+]i 的作用不会导致一氧化氮信号的改变。酪氨酸磷酸化不参与植物雌激素对[Ca2+]i 升高的抑制作用，因为酪氨酸激酶抑制剂染料木素和其非活性类似物染料木素对凝血酶诱导的[Ca2+]i 升高和硫辛酸诱导的[Ca2+]i 升高的抑制百分比在任何测试浓度下都没有显著差异。对这组有限化合物进行的结构-活性关系研究揭示了钙阻断活性对芪类药物结构的要求。
• [EN] PRODUCTION OF ISOFLAVONE DERIVATIVES<br/>[FR] DERIVES D'ISOFLAVONE
  申请人：NOVOGEN RES PTY LTD

  公开号：WO2000049009A1

  公开（公告）日：2000-08-24

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  本文描述了一些对异黄酮进行氢化的方法，可以获得可用量的异黄酮-4-醇、异黄酮-3-烯和异黄酮。在使用药用可接受试剂和溶剂的同时，可以高纯度地获得异黄酮衍生物，并且接近定量收率。
• Compounds for immunopotentiation
  申请人：Valiante Nicholas

  公开号：US20100226931A1

  公开（公告）日：2010-09-09

  Methods of stimulating an immune response and treating patients responsive thereto with 3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-diones, staurosporine analogs, derivatized pyridazines, chromen-4-ones, indolinones, quinazolines, nucleoside analogs, and other small molecules are disclosed. In a preferred embodiment benzopyrimidine derivatives such as ZD-6474, MLN-518, lapatinib, gefitinib or erlotinib are used.

  本发明公开了刺激免疫反应和治疗对3,4-二（1H-吲哚-3-基）-1H-吡咯-2,5-二酮，链霉菌素类似物，衍生的吡啶并嗪，香豆素-4-酮，吲哚酮，喹唑啉，核苷类似物和其他小分子具有响应性的患者。在一种优选实施方式中，使用苯并嘧啶衍生物，例如ZD-6474，MLN-518，拉帕替尼，吉非替尼或厄洛替尼。

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