5-hydroxy-6-methoxy-2-phenyl-7-(4-(pyrrolidin-1-yl)butoxy)-4H-chromen-4-one | 1263323-17-6

• 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: 5-hydroxy-6-methoxy-2-phenyl-7-(4-(pyrrolidin-1-yl)butoxy)-4H-chromen-4-one
• 英文别名: 5-Hydroxy-6-methoxy-2-phenyl-7-(4-pyrrolidin-1-ylbutoxy)chromen-4-one
• CAS: 1263323-17-6
• 化学式: C₂₄H₂₇NO₅
• 分子量: 409.482
• InChiKey: LEUMJIDRAMOIKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  千层纸素A 在 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 5-hydroxy-6-methoxy-2-phenyl-7-(4-(pyrrolidin-1-yl)butoxy)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 7-O-modified oroxylin A derivatives

  摘要：

  Oroxylin A (5,7-dihydroxy-6-methoxyflavone) is a naturally occurring monoflavonoid isolated from the root of Scutellaria baicalensis Georgi, and exhibits potent anticancer activities in vitro and in vivo. In this study, we synthesized three series of oroxylin derivatives by connecting a nitrogen-containing hydrophilic, heterocyclic ring to the C7-OH via a varying length of carbon chain. All the derivatives were screened for anti-proliferative activities against three tumor cell lines. Some of the derivatives displayed higher activities compared to oroxylin A. The most potent antitumor compound, 5f, also induced apoptosis in HepG2 cell. The difference of 5f between the inhibiting rates of cell proliferation and the apoptotic rates indicated that Sf was more likely to be a necrosis-inducing agent or both apoptosis/necrosis inducer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.117

文献信息

• 10.1021/acs.oprd.4c00082
  作者：Shen, Pei、Wang, Yezhi、Yu, Sixian、Du, Yu、Li, Zhiyu、Wang, Jubo

  DOI：10.1021/acs.oprd.4c00082

  日期：——

  GL-V9, an innovative synthetic flavonoid derivative, has been submitted to Investigational New Drug (IND) application to the National Medical Products Administration (NMPA) in 2023 for the treatment of acute myeloid leukemia. This study details the development of an advanced, efficient synthesis pathway for GL-V9, enabling the production of significant quantities of the drug substance to fulfill the

  GL-V9是一种创新的合成类黄酮衍生物，已于2023年向国家药品监督管理局（NMPA）提交新药（IND）申请，用于治疗急性髓系白血病。这项研究详细介绍了 GL-V9 先进、高效的合成途径的开发，从而能够生产大量的药物，以满足即将进行的临床试验的需求。该方法的特点是在温和条件下进行五步反应——以市售白杨素为起始原料，经过Elbs氧化、 O-烷基化、水解、甲基化、 N-烷基化结束，以优异的高效液相色谱法获得GL-V9纯度（>99.5面积%）和29.1%的总产率。重要的是，GL-V9的合成为其他黄酮类支架的开发引入了通用框架，强调了其在药物化学领域的广泛适用性。这种可扩展且高效的途径不仅促进了 GL-V9 的生产，而且还为探索新型类黄酮疗法开辟了途径。
• Synthesis and biological evaluation of 7-O-modified oroxylin A derivatives
  作者：Wei Fu、Jubo Wang、Liqin Yu、Li Zhao、Na Lu、Qidong You、Qinglong Guo、Zhiyu Li

  DOI：10.1016/j.bmcl.2011.11.117

  日期：2012.1

  Oroxylin A (5,7-dihydroxy-6-methoxyflavone) is a naturally occurring monoflavonoid isolated from the root of Scutellaria baicalensis Georgi, and exhibits potent anticancer activities in vitro and in vivo. In this study, we synthesized three series of oroxylin derivatives by connecting a nitrogen-containing hydrophilic, heterocyclic ring to the C7-OH via a varying length of carbon chain. All the derivatives were screened for anti-proliferative activities against three tumor cell lines. Some of the derivatives displayed higher activities compared to oroxylin A. The most potent antitumor compound, 5f, also induced apoptosis in HepG2 cell. The difference of 5f between the inhibiting rates of cell proliferation and the apoptotic rates indicated that Sf was more likely to be a necrosis-inducing agent or both apoptosis/necrosis inducer. (C) 2011 Elsevier Ltd. All rights reserved.