toddaliopsin A | 33130-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: toddaliopsin A
• 英文别名: 1,2,3-trimethoxy-10H-acridin-9-one
• CAS: 33130-09-5
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: ZUOLILKPUZXGOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  toddaliopsin A 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 水 、 mineral oil 为溶剂， 反应 14.0h， 生成 山小柑碱
  参考文献：
  名称：

  Synthesis of novel heme-interacting acridone derivatives to prevent free heme-mediated protein oxidation and degradation

  摘要：

  Heme is an important prosthetic molecule for various hemoproteins and serves important function in living aerobic organisms. But degradation of hemoprotein, for example, hemoglobin during different pathological conditions leads to the release of heme, which is very toxic as it induces oxidative stress and inflammation due to its pro-oxidant nature. Thus, synthesis of compound that will detoxify free heme by interacting with it would be fruitful for the management of heme-induced pathogenesis. Here, we report the synthesis of a novel natural product arborinine and some other acridone derivatives, which interact with free heme. These acridones in vitro block heme-mediated protein oxidation and degradation, markers for heme-induced oxidative stress. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.127
• 作为产物：
  描述：

  5-碘-1,2,3-三甲氧基苯 在 copper(I) oxide 、 Eaton's reagent 、 铜 、 potassium carbonate 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 5.83h， 生成 toddaliopsin A
  参考文献：
  名称：

  Synthesis of novel heme-interacting acridone derivatives to prevent free heme-mediated protein oxidation and degradation

  摘要：

  Heme is an important prosthetic molecule for various hemoproteins and serves important function in living aerobic organisms. But degradation of hemoprotein, for example, hemoglobin during different pathological conditions leads to the release of heme, which is very toxic as it induces oxidative stress and inflammation due to its pro-oxidant nature. Thus, synthesis of compound that will detoxify free heme by interacting with it would be fruitful for the management of heme-induced pathogenesis. Here, we report the synthesis of a novel natural product arborinine and some other acridone derivatives, which interact with free heme. These acridones in vitro block heme-mediated protein oxidation and degradation, markers for heme-induced oxidative stress. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.127

文献信息

• Weakly Coordinating, Ketone-Directed (η⁵ -Pentamethylcyclopentadienyl)cobalt(III)- and (η⁵ -Pentamethylcyclopentadienyl)rhodium(III)-Catalyzed C−H Amidation of Arenes: A Route to Acridone Alkaloids
  作者：Sourav Sekhar Bera、Md Raja Sk、Modhu Sudan Maji

  DOI：10.1002/chem.201805376

  日期：2019.2.1

  monoamidation of aromatic ketones, chalcone, carbazole, and benzophenones was achieved by employing high‐valent cobalt and rhodium catalysis to access numerous biologically important molecular building blocks. This amidation proceeded smoothly with a variety of ketones and several amidating partners. The application of the products in the synthesis of various heterocycles, including acridones, indoles, quinoline

  芳香族酮，查尔酮，咔唑和二苯甲酮的弱配位，酮定向，区域选择性单酰胺化是通过使用高价钴和铑催化作用来获得许多生物学上重要的分子构件而实现的。该酰胺化反应与各种酮和一些酰胺化伙伴一起进行得很顺利。还研究了产物在各种杂环的合成中的应用，包括including啶，吲哚，喹啉，喹诺酮，喹啉酮和喹唑啉。通过这种方法，也可以完成基于cri啶酮的生物碱的总合成，即托达洛辛A，托达洛辛D和Arborinine，以及正式合成了丙烯醛和诺拉霉素。
• A Novel Palladium-Based Heterogeneous Catalyst for Tandem Annulation: A Strategy for Direct Synthesis of Acridones
  作者：Darío C. Gerbino、H. Sebastián Steingruber、Pamela Mendioroz、M. Julia Castro、María A. Volpe

  DOI：10.1055/s-0042-1751371

  日期：2023.2

  In order to develop an efficient, rapid, and modular cascade strategy for the direct synthesis of acridones, palladium supported on sulfated alumina and microwave activation are employed. Multifunctional heterogeneous palladium catalysts were prepared in order to carry out the sequential annulation via a Buchwald–Hartwig amination followed by an intramolecular annulation in a one-pot process. This

  为了开发用于直接合成吖啶酮的高效、快速和模块化级联策略，采用负载在硫酸化氧化铝上的钯和微波活化。制备了多功能非均相钯催化剂，以通过 Buchwald-Hartwig 胺化进行顺序环化，然后在一锅法中进行分子内环化。这一新协议代表了第一份关于在无配体条件下从市售起始材料催化串联合成吖啶酮衍生物的报告。本方法的范围扩展到生成功能化吖啶酮文库，显示出高官能团兼容性，产率适中至极好。
• Hughes et al., Australian Journal of Scientific Research, Series A: Physical Sciences, 1950, vol. 3, p. 497,500
  作者：Hughes et al.

  DOI：——

  日期：——
• Cannon et al., Australian Journal of Scientific Research, Series A: Physical Sciences, 1952, vol. 5, p. 406,408,410
  作者：Cannon et al.

  DOI：——

  日期：——
• Synthesis of novel heme-interacting acridone derivatives to prevent free heme-mediated protein oxidation and degradation
  作者：Chinmay Pal、Milan Kumar Kundu、Uday Bandyopadhyay、Susanta Adhikari

  DOI：10.1016/j.bmcl.2011.04.127

  日期：2011.6

  Heme is an important prosthetic molecule for various hemoproteins and serves important function in living aerobic organisms. But degradation of hemoprotein, for example, hemoglobin during different pathological conditions leads to the release of heme, which is very toxic as it induces oxidative stress and inflammation due to its pro-oxidant nature. Thus, synthesis of compound that will detoxify free heme by interacting with it would be fruitful for the management of heme-induced pathogenesis. Here, we report the synthesis of a novel natural product arborinine and some other acridone derivatives, which interact with free heme. These acridones in vitro block heme-mediated protein oxidation and degradation, markers for heme-induced oxidative stress. (C) 2011 Elsevier Ltd. All rights reserved.