8-acetylchrysin | 32374-76-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 8-acetylchrysin
• 英文别名: 8-Acetyl-5,7-dihydroxyflavon；8-acetyl-5,7-dihydroxy-2-phenyl-chromen-4-one；8-Acetyl-5,7-dihydroxy-2-phenylchromen-4-one
• CAS: 32374-76-8
• 化学式: C₁₇H₁₂O₅
• 分子量: 296.279
• InChiKey: ZUZWEGDHMVDTBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-羟基哌啶 、 聚合甲醛 、 8-acetylchrysin 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 8-acetyl-5,7-dihydroxy-6-(4-hydroxypiperidin-1-ylmethyl)-2-phenylchromen-4-one
  参考文献：
  名称：

  乙酰基白杨素Mannich碱衍生物及其用途

  摘要：

  乙酰基白杨素Mannich碱衍生物及其用途，所述衍生物具有通式I的结构，其中，R1和R2各自独立地选自乙酰基和有机仲胺亚甲基，R1与R2中有且只有一个是乙酰基。该类化合物是一种ROS调控的缺氧诱导转录因子(HIF‑1α)抑制剂，利用正常细胞和肿瘤细胞内氧化和还原的不同机制，通过捕获细胞内氧自由基，特异性提高肿瘤细胞内过氧化氢水平，靶向氧化降解HIF‑1α和氧化激活Caspases，激活细胞内凋亡通路，从而选择性诱导肿瘤细胞凋亡并抑制增殖和转移。该类化合物对实体瘤具有良好的选择性。并且药代动力学性质独特，高效低毒，作用机理明确。全合成原料来源丰富，工艺简捷，纯度高，成本低。

  公开号：

  CN106117189B

文献信息

• CDK1 inhibitors of acetyl chrysin mannich base derivatives, synthesis and use thereof
  申请人：Zhang Fan

  公开号：US10471054B2

  公开（公告）日：2019-11-12

  Provided is a series of acetyl Chrysin Mannich base derivatives with the structures illustrated in the following scheme: wherein R1 is acetyl and R2 is cycloalkylamine-methyl, or R2 is acetyl and R1 is cycloalkylamine-methyl. Such derivatives are cyclin-dependent protein kinases 1 (CDK1) selective inhibitors. Base on the levels of .O2− and Fe++ are higher 5-15 times in cancer cells than in normal cells, the action mechanism of such derivatives by regulating intracellular reactive oxygen species (ROS) is activating mitochondria apoptosis pathway without the death receptor pathway, thus selectively inducing apoptosis of cancer cells and protecting normal cells. Inside, CH-j has a good druggability for the selectivity of solid cancers. Moreover, CH-f has also a good druggability for the systemic cancers.

  本研究提供了一系列乙酰基 Chrysin Mannich 碱衍生物，其结构如下图所示：其中 R1 是乙酰基，R2 是环烷基胺甲基，或 R2 是乙酰基，R1 是环烷基胺甲基。这类衍生物是细胞周期蛋白依赖性蛋白激酶 1（CDK1）选择性抑制剂。基于癌细胞中.O2-和Fe++的水平比正常细胞高5-15倍，此类衍生物通过调节细胞内活性氧（ROS）的作用机制是激活线粒体凋亡途径，而不是死亡受体途径，从而选择性地诱导癌细胞凋亡，保护正常细胞。其中，CH-j 对实体瘤的选择性具有良好的可药性。此外，CH-f 对全身性癌症也有良好的可药性。
• CDK1 INHIBITORS OF ACETYL CHRYSIN MANNICH BASE DERIVATIVES, SYNTHESIS AND USE THEREOF
  申请人：ZHANG Fan

  公开号：US20190216792A1

  公开（公告）日：2019-07-18

  Provided is a series of acetyl Chrysin Mannich base derivatives with the structures illustrated in the following scheme: wherein R 1 is acetyl and R 2 is cycloalkylamine-methyl, or R 2 is acetyl and R 1 is cycloalkylamine-methyl. Such derivatives are cyclin-dependent protein kinases 1 (CDK1) selective inhibitors. Base on the levels of .O 2 − and Fe ++ are higher 5-15 times in cancer cells than in normal cells, the action mechanism of such derivatives by regulating intracellular reactive oxygen species (ROS) is activating mitochondria apoptosis pathway without the death receptor pathway, thus selectively inducing apoptosis of cancer cells and protecting normal cells. Inside, CH-j has a good druggability for the selectivity of solid cancers. Moreover, CH-f has also a good druggability for the systemic cancers.