3-(4-bromobutoxy)-1-hydroxy-9H-xanthen-9-one | 1242438-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(4-bromobutoxy)-1-hydroxy-9H-xanthen-9-one
• 英文别名: 3-(4-Bromobutoxy)-1-hydroxyxanthen-9-one；3-(4-bromobutoxy)-1-hydroxyxanthen-9-one
• CAS: 1242438-21-6
• 化学式: C₁₇H₁₅BrO₄
• 分子量: 363.208
• InChiKey: BDZJKRIVLYVTJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-bromobutoxy)-1-hydroxy-9H-xanthen-9-one 以 乙醇 、 氯仿 为溶剂， 反应 72.5h， 生成 4-(1-hydroxy-9-oxo-9H-xanthen-3-yloxy)-N,N,N-trimethylbutan-1-aminium iodide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 1-hydroxyl-3-aminoalkoxy xanthone derivatives as potent anticancer agents

  摘要：

  A series of novel 1-hydroxyl-3-aminoalkoxy xanthone derivatives were designed, synthesized and evaluated for in vitro anticancer activity against four selected human cancer cell lines (nasopharyngeal neoplasm CNE, liver cancer BEL-7402, gastric cancer MGC-803, lung adenocarcinoma A549). Most of the synthesized compounds exhibit effective cytotoxic activity against the four tested cancer cell lines with the IC50 values at micromolar concentration level. Some preliminary structure activity relationships were also discussed. In this series of derivatives, compound 3g shows excellent broad spectrum anticancer activity with IC50 values ranging from 3.57 to 20.07 mu M. The in vitro anticancer activity effect and action mechanism of compound 3g on human gastric carcinoma MGC-803 cell were further investigated. The results showed that compound 3g exhibits dose- and time-dependent anticancer effects on MGC-803 cells through apoptosis, which might be associated with its decreasing intracellular calcium and the mitochondrial membrane potential. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.076
• 作为产物：
  描述：

  间苯三酚 在 potassium carbonate 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 3-(4-bromobutoxy)-1-hydroxy-9H-xanthen-9-one
  参考文献：
  名称：

  将一氧化氮供体掺入1,3-二氧杂蒽酮中会产生协同的抗癌活性

  摘要：

  五十1,3- dioxyxanthone硝酸盐（4A〜中，N = 1-6），设计并基于分子相似策略合成。将硝酸盐掺入1,3-二氧杂蒽酮中具有给电子基团的6-8位可产生协同的抗癌作用。其中，化合物4g-4被证实是最有效的抗HepG-2细胞生长的药物，IC 50为0.33±0.06μM。它剂量依赖性地增加了分子内NO水平。NO清除剂PTIO或线粒体醛脱氢酶（mtADH）抑制剂PCDA减弱了这种活性。凋亡分析表明，对于不同剂量的4g-4，早期/晚期凋亡和坏死对细胞死亡的不同贡献。4克-4在S期捕获更多的细胞。Western Blot的结果表明4g-4调节p53 / MDM2促进癌细胞凋亡。所有证据都支持4g-4是一种有前途的抗癌药。

  DOI：

  10.1016/j.ejmech.2018.03.072

文献信息

• 一种Xanthone-NO供体化合物及其制备方法 和在制备抗肿瘤药物中的应用
  申请人：暨南大学

  公开号：CN107602522B

  公开（公告）日：2019-12-24

  本发明属于抗肿瘤药物技术领域，公开了一种Xanthone‑NO供体化合物及其制备方法和在制备抗肿瘤药物中的应用。本发明的Xanthone‑NO供体化合物具有式Ⅰ所示的结构：其中，R1、R2、R3相同或不同的分别为H、OH、Cl、Br或F；n＝2～8。本发明制备方法为由取代水杨酸与间苯三酚制备xanthones，然后与1,n‑二溴取代烷反应制备3‑O‑溴代烷基xanthone，再溴转化得到。本发明化合物对乳腺癌、肝癌细胞具有优良的体外肿瘤细胞增殖抑制活性，并且能多靶点诱导肿瘤细胞的凋亡，因此可应用于制备抗肿瘤药物中，特别多靶点治疗癌症药物及由一氧化氮异常所引起肿瘤的药物。
• Design, synthesis, and biological evaluation of novel xanthone-alkylbenzylamine hybrids as multifunctional agents for the treatment of Alzheimer’s disease
  作者：Zhipeng Zhang、Jie Guo、Maojun Cheng、Weixin Zhou、Yang Wan、Rikang Wang、Yuanying Fang、Yi Jin、Jing Liu、Sai-Sai Xie

  DOI：10.1016/j.ejmech.2021.113154

  日期：2021.3

  In this study, a series of multifunctional hybrids against Alzheimer’s disease were designed and obtained by conjugating the pharmacophores of xanthone and alkylbenzylamine through the alkyl linker. Biological activity results demonstrated that compound 4j was the most potent and balanced dual ChEs inhibitor with IC50 values 0.85 μM and 0.59 μM for eeAChE and eqBuChE, respectively. Kinetic analysis

  在这项研究中，设计了一系列针对阿尔茨海默氏病的多功能杂种，方法是通过烷基连接体缀合蒽酮和烷基苄胺的药效基团。生物活性结果表明，化合物4j是最有效和平衡的双重ChEs抑制剂，eeAChE和eqBuChE的IC 50值分别为0.85μM和0.59μM。动力学分析和对接研究表明，化合物4j是AChE和BuChE的混合型抑制剂。此外，它还具有很好的渗透BBB，清除自由基（4.6 trolox当量）以及与Cu 2+和Al 3+选择性螯合的能力。配体/金属摩尔比为1：1.4。重要的是，在评估细胞毒性和急性毒性后，我们发现化合物4j可以改善东amine碱诱导的失忆症小鼠的记忆功能。因此，化合物4j可被认为是有前途的先导化合物，用于AD治疗中的进一步研究。
• Incorporation of nitric oxide donor into 1,3-dioxyxanthones leads to synergistic anticancer activity
  作者：Jie Liu、Cao Zhang、Huailing Wang、Lei Zhang、Zhenlei Jiang、Jianrun Zhang、Zhijun Liu、Heru Chen

  DOI：10.1016/j.ejmech.2018.03.072

  日期：2018.5

  based on molecular similarity strategy. Incorporation of nitrate into 1,3-dioxyxanthones with electron-donating groups at 6–8 position brought about synergistic anticancer effect. Among them, compound 4g-4 was confirmed the most active agent against HepG-2 cells growth with an IC50 of 0.33 ± 0.06 μM. It dose-dependently increased intramolecular NO levels. This activity was attenuated by either NO scavenger

  五十1,3- dioxyxanthone硝酸盐（4A〜中，N = 1-6），设计并基于分子相似策略合成。将硝酸盐掺入1,3-二氧杂蒽酮中具有给电子基团的6-8位可产生协同的抗癌作用。其中，化合物4g-4被证实是最有效的抗HepG-2细胞生长的药物，IC 50为0.33±0.06μM。它剂量依赖性地增加了分子内NO水平。NO清除剂PTIO或线粒体醛脱氢酶（mtADH）抑制剂PCDA减弱了这种活性。凋亡分析表明，对于不同剂量的4g-4，早期/晚期凋亡和坏死对细胞死亡的不同贡献。4克-4在S期捕获更多的细胞。Western Blot的结果表明4g-4调节p53 / MDM2促进癌细胞凋亡。所有证据都支持4g-4是一种有前途的抗癌药。
• Design, synthesis and biological evaluation of novel 1-hydroxyl-3-aminoalkoxy xanthone derivatives as potent anticancer agents
  作者：Zheng-Min Yang、Jun Huang、Jiang-Ke Qin、Zhi-Kai Dai、Wen-Li Lan、Gui-Fa Su、Huang Tang、Feng Yang

  DOI：10.1016/j.ejmech.2014.07.076

  日期：2014.10

  A series of novel 1-hydroxyl-3-aminoalkoxy xanthone derivatives were designed, synthesized and evaluated for in vitro anticancer activity against four selected human cancer cell lines (nasopharyngeal neoplasm CNE, liver cancer BEL-7402, gastric cancer MGC-803, lung adenocarcinoma A549). Most of the synthesized compounds exhibit effective cytotoxic activity against the four tested cancer cell lines with the IC50 values at micromolar concentration level. Some preliminary structure activity relationships were also discussed. In this series of derivatives, compound 3g shows excellent broad spectrum anticancer activity with IC50 values ranging from 3.57 to 20.07 mu M. The in vitro anticancer activity effect and action mechanism of compound 3g on human gastric carcinoma MGC-803 cell were further investigated. The results showed that compound 3g exhibits dose- and time-dependent anticancer effects on MGC-803 cells through apoptosis, which might be associated with its decreasing intracellular calcium and the mitochondrial membrane potential. (C) 2014 Elsevier Masson SAS. All rights reserved.