7-氧代-7H-二苯并[de,g]喹啉 | 38750-39-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 中文名称: 7-氧代-7H-二苯并[de,g]喹啉
• 英文名称: 7H-dibenzo[de,g]quinolin-7-one
• 英文别名: 7-Oxo-7H-dibenzo[de,g]quinoline；10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one
• CAS: 38750-39-9
• 化学式: C₁₆H₉NO
• 分子量: 231.254
• InChiKey: GHWKWAMIXPOYPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-碘异喹啉 在 sodium tetrahydroborate 、 sodium hydride 、 sodium amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.0h， 生成 7-氧代-7H-二苯并[de,g]喹啉
  参考文献：
  名称：

  1-（2-溴苯甲酰基）异喹啉通过还原性光环化反应直接转化为二苯并[ de，g ]喹啉-7-酮

  摘要：

  由相应的异喹啉酮和（2-溴苯基）乙腈分四个步骤制得一系列A / D环取代的二苯并[ de，g ]喹啉-7-酮。这代表了合成四环生物碱的简便方法。1-（2-溴苯甲酰基）异喹啉直接转化为二苯并[ de，g ]喹啉-7-酮是总合成中的关键步骤。还原性光环化的产率取决于异喹啉基环和苯基上取代基的位置。还讨论了还原性光环化的机理。

  DOI：

  10.1021/jo400645g

文献信息

• Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine
  作者：Tibor Soós、Dániel Horváth、Frigyes Domonyi、Roberta Palkó、Andrea Lomoschitz

  DOI：10.1055/s-0037-1609153

  日期：2018.6

  functionalization of the carbocyclic core of the isoquinoline. This regioexhaustive approach employs electrophilic halogenation as a toolbox methodology and delivers highly decorated intermediates that can be further elaborated toward medicinally relevant building blocks or natural products. A general and versatile strategy has been developed for the functionalization of the carbocyclic core of the isoquinoline. This

  摘要 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。
• One-pot synthesis of oxoaporphines as potent antitumor agents and investigation of their mechanisms of actions
  作者：Lan-Shan Liao、Lin-Jie Tan、Yin Chen、Qi-Yuan Yang、Muhammad Iqbal Choudhary、Ying-Ming Pan、Hai-Tao Tang、Gui-Fa Su、Hong Liang、Zhen-Feng Chen

  DOI：10.1016/j.ejmech.2022.114141

  日期：2022.3

  efficient one-pot reaction for the synthesis of oxoaporphine alkaloids has been developed. Twenty-three compounds of oxoaporphine alkaloids were prepared and assessed for their antitumor activities. Most compounds inhibited the growth of T-24 tumor cells in vitro. Particularly, 4B displayed the most potent activity with an IC50 value of 0.5 μM, which was 19-fold more potent than the parent compound 4. The

  已经开发了一种用于合成氧代卟啉生物碱的有效一锅法反应。制备并评估了 23 种氧代卟啉生物碱化合物的抗肿瘤活性。大多数化合物在体外抑制 T-24 肿瘤细胞的生长。特别是，4B显示出最有效的活性，其 IC 50值为 0.5 μM，比母体化合物4强 19 倍。-NO 2在氧代卟啉核心的C3位取代显着增强了抗癌活性。机制研究表明，4和4B诱导细胞周期停滞在G2/M期；相比之下，4V诱导细胞周期停滞在 S 期。T-24细胞暴露于化合物4、4B和4V后观察到线粒体ROS/Ca 2+增加和MMP减少，并伴有caspase-3/9活化，提示线粒体途径参与诱导的细胞凋亡。此外，化合物4B在带有 T-24 的小鼠异种移植模型中有效抑制肿瘤生长。
• Design, synthesis and anticancer activity of oxoaporphine alkaloid derivatives
  作者：Yong-Biao Wei、Ying-Xin Li、Hui Song、Xian-Jin Feng

  DOI：10.3109/14756366.2013.845818

  日期：2014.10.1

  A series of new oxoaporphine derivatives were synthesized and their inhibitory activity of topoisomerase I, cytotoxicity and DNA-binding properties were studied. Oxoaporphine can strongly inhibit topoisomerase I at concentrations of 5-50 µM and the cytotoxicity of the derivatives are more potent than their lead compound. Hypochromism, broadening and red shift in the absorption spectra were observed when these compounds bind to calf thymus DNA (CT DNA). These spectral characteristics were consistent with the intercalative binding of these compounds.
• Direct Conversion of 1-(2-Bromobenzoyl)isoquinolines to Dibenzo[<i>de,g</i>]quinolin-7-ones via Reductive Photocyclization
  作者：Ta-Hsien Chuang、Chien-Fu Li、Hong-Zin Lee、Yu-Chia Wen

  DOI：10.1021/jo400645g

  日期：2013.5.17

  from the corresponding isoquinolinones and (2-bromophenyl)acetonitriles in four steps. This represents a convenient approach toward the synthesis of tetracyclic alkaloids. A direct conversion of 1-(2-bromobenzoyl)isoquinolines to dibenzo[de,g]quinolin-7-ones is the key step in the total synthesis. The yield of the reductive photocyclization depends on the position of the substituents at the isoquinolyl

  由相应的异喹啉酮和（2-溴苯基）乙腈分四个步骤制得一系列A / D环取代的二苯并[ de，g ]喹啉-7-酮。这代表了合成四环生物碱的简便方法。1-（2-溴苯甲酰基）异喹啉直接转化为二苯并[ de，g ]喹啉-7-酮是总合成中的关键步骤。还原性光环化的产率取决于异喹啉基环和苯基上取代基的位置。还讨论了还原性光环化的机理。