daunorubicin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: daunorubicin
• 英文别名: (7S,9S)-9-acetyl-7-[(4-amino-5-hydroxy-6-methyl-2-oxanyl)oxy]-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione；(7S,9S)-9-acetyl-7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• 化学式: C₂₇H₂₉NO₁₀
• 分子量: 527.528
• InChiKey: STQGQHZAVUOBTE-JYZNYWJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  186
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  daunorubicin 、 γ-环糊精 生成
  参考文献：
  名称：

  γ-环糊精-柔红霉素包合物与鲱鱼精子DNA相互作用的光谱研究

  摘要：

  摘要 采用紫外-可见吸收光谱法、荧光光谱法和粘度法研究了柔红霉素（DNR）与鲱鱼精DNA在环麦芽糖（γ-环糊精，简称γ-CD）超分子体系中的相互作用。在生理pH条件下，结果表明DNR更倾向于与γ-CD形成1:1的包合物。红外光谱 (IR) 和 X 射线衍射 (XRD) 进一步支持了这些结果。根据吸光度变化，形成 γ-CD-DNR 包合物的包合常数 (K) 为 9412.39 L mol -1。观察到γ-CD-DNR与DNA的相互作用模式是混合结合，包含部分嵌入和凹槽结合。γ-CD-DNR 与 DNA 的结合比为 n γ-CD-DNR：n DNA = 10:1，结合常数为 K Θ 298.15 K = 2。

  DOI：

  10.1016/j.carbpol.2010.09.032

文献信息

• METHOD OF PRODUCING 4-DEMETHOXYDAUNORUBICIN
  申请人：Zabudkin Alexander

  公开号：US20120277415A1

  公开（公告）日：2012-11-01

  The present invention relates to a method for the synthesis of 4-demethoxydaunorubicin (idarubicin) having the chemical structure of formula (I), which involves the demethylation of 3′-Prot-daunorubicin in the presence of a soft Lewis acid. The method of the present invention does not comprise cleavage of the glycosidic linkage at carbon C7, thus resulting in a faster synthesis cycle and an improved yield of the final product.

  本发明涉及一种合成4-去甲氧基多柔红霉素（伊达霉素）的方法，其化学结构如式（I），该方法涉及在软性Lewis酸存在下对3'-Prot-多柔红霉素进行去甲基化。本发明的方法不包括在碳C7处断裂糖苷键，因此导致合成周期更快，最终产物的产率提高。
• METHOD FOR PREPARING 4-DEMETHYLDAUNORUBICIN
  申请人：Zabudkin F. Alexander

  公开号：US20070135624A1

  公开（公告）日：2007-06-14

  A method of preparing the anthracyclin carminomycin using a starting material comprising daunorubicin. The method comprises reacting daunorubicin or N-protected daunorubicin with soft Lewis acids for the demethylation of the 4-methoxy group, resulting in a reaction mass. The reaction mass is treated with an aqueous solution of a strong organic acid or a mineral acid. After decomposition of the resulting carminomycin and Lewis acids reactive complex, the reaction mass is extracted using a water insoluble organic solvent. As a result, carminomycin is extracted as a base.

  使用含有多柔比星的起始物质制备蒽环类卡米诺霉素的方法。该方法包括将多柔比星或N-保护的多柔比星与软路易斯酸反应，以去甲基化4-甲氧基团，形成反应混合物。将反应混合物与强有机酸或矿物酸的水溶液处理。在分解产生的卡米诺霉素和路易斯酸反应复合物后，使用水不溶性有机溶剂提取反应混合物。结果，卡米诺霉素以碱的形式被提取。
• [EN] ALPHA HELIX MIMETICS AND METHODS RELATING THERETO<br/>[FR] MIMÉTIQUES D'HÉLICE ALPHA ET PROCÉDÉS ASSOCIÉS
  申请人：PRISM BIOLAB CORP

  公开号：WO2010128685A1

  公开（公告）日：2010-11-11

  Alpha-helix mimetic structures and compounds represented by the formula (I) wherein the general formula and the definition of each symbol are as defined in the specification, a chemical library relating thereto, and methods relating thereto, are disclosed. Applications of these compounds in the treatment of medical conditions, e.g., cancer diseases, fibrotic diseases, and pharmaceutical compositions comprising the mimetics are further disclosed.

  α-螺旋拟态结构和由式(I)代表的化合物，其中一般公式和每个符号的定义如规范中所定义，相关的化学库以及相关方法被披露。还披露了这些化合物在治疗医疗状况（例如癌症疾病、纤维化疾病）中的应用，以及包含这些拟态体的药物组成。
• AMYLOID-BINDING COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Vanderbilt University

  公开号：US20210011008A1

  公开（公告）日：2021-01-14

  A method of screening for amyloid-binding compounds, amyloid-binding compounds, and a method of detecting amyloid-β (Abeta) plaques in a subject are disclosed. The method of screening for amyloid-binding compounds includes combining amyloid, a dye, and at least one test compound to form a sample solution; equilibrating the sample solution; measuring a fluorescence signal of the sample solution; and comparing the measured fluorescence signal of the sample to a control; wherein attenuation of the fluorescence signal, as compared to the control, indicates that one or more of the test compounds bind amyloid. The amyloid-binding compound includes a compound detected by the screening method. The method of detecting amyloid-β (Abeta) plaques in a subject includes administering one or more of the amyloid-binding compounds to the subject, and detecting the compound within the subject.

  揭示了一种筛选淀粉样结合化合物、淀粉样结合化合物的方法，以及检测受试者中淀粉-β（Abeta）斑块的方法。筛选淀粉样结合化合物的方法包括将淀粉、染料和至少一种试剂化合物组合以形成样品溶液；平衡样品溶液；测量样品溶液的荧光信号；并将所测得的样品的荧光信号与控制进行比较；其中，与控制相比减弱的荧光信号表明一个或多个试剂化合物与淀粉结合。淀粉样结合化合物包括通过筛选方法检测到的化合物。在受试者中检测淀粉-β（Abeta）斑块的方法包括向受试者施用一个或多个淀粉样结合化合物，并在受试者内检测化合物。
• METHOD OF ARALKYLATION OF 4'-HYDROXYL GROUP OF ANTHRACYLINS
  申请人：Zabudkin Alexander F.

  公开号：US20090176974A1

  公开（公告）日：2009-07-09

  A method for the aralkylation of anthracyclins by utilizing an aralkylating agent R 3- CH 2 X (for example, BnBr) in accordance with the reaction pathway describe by the scheme shown in FIG. 1 . The present invention recognizes that 4-R 1 , 3′-N 3 -Daunomycines are suitable substrates for selective 4′-O-benzylation, yielding 4-R 1 , 3′-N 3 -4′-O-Aralkyl-Daunorubicines (in particular, 4′-O-Bn-Daunomycines). Thus, the present invention provides a pathway for a simple production of 4′-O-aralkylated derivatives of anthracyclines which can be effectively used to produce anthracyclines.

  一种用于利用芳基化试剂R3-CH2X（例如，BnBr）对蒽喜树碱进行芳基化的方法，符合图1所示的反应途径描述的方案。本发明认识到4-R1, 3'-N3-多柔米辛是适合选择性4'-O-苄基化的底物，产生4-R1, 3'-N3-4'-O-芳基-多柔比辛（特别是4'-O-Bn-多柔米辛）。因此，本发明提供了一种简单生产蒽喜树碱的4'-O-芳基化衍生物的途径，这些衍生物可以有效用于生产蒽喜树碱。