7-bromo-1,3-dihydroxy-9H-xanthen-9-one | 100334-97-2

• 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: 7-bromo-1,3-dihydroxy-9H-xanthen-9-one
• 英文别名: 7-bromo-1,3-dihydroxyxanthone；7-bromo-1,3-dihydroxyxanthen-9-one
• CAS: 100334-97-2
• 化学式: C₁₃H₇BrO₄
• mdl: MFCD13969029
• 分子量: 307.1
• InChiKey: UELZRCNDZXKHEF-UHFFFAOYSA-N

物化性质

• 沸点：
  538.7±39.0 °C(Predicted)
• 密度：
  1.842±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  7-bromo-1,3-dihydroxy-9H-xanthen-9-one 在 吡啶 、 potassium osmate(VI) dihydrate 、 四(三苯基膦)钯 、 (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan) 、 甲基磺酰胺 、 水 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  Anti-AIDS agents 85. Design, synthesis, and evaluation of 1R,2R-dicamphanoyl-3,3-dimethyldihydropyrano-[2,3-c]xanthen-7(1H)-one (DCX) derivatives as novel anti-HIV agents

  摘要：

  In this study, 1R,2R-dicamphanoyl-3,3-dimethydihydropyrano[2,3-c]xanthen-7(1H)-one (DCX) derivatives were designed and synthesized as novel anti-HIV agents against both wild-type and non-nucleoside reverse transcriptase (RT) inhibitor-resistant HIV-1 (RTMDR-1) strains. Twenty-four DCX analogs (6-29) were synthesized and evaluated against the non-drug-resistant HIV-1 NL4-3 strain, and selected analogs were also screened for their ability to inhibit the RTMDR-1 strain. Compared with the control 2-ethyl-3',4'-di-O-(-)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (2-EDCP, 2), one of the best anti-HIV coumarin derivatives in our prior study, three DCX compounds (7, 12, and 22) showed better activity against both HIV strains with an EC50 range of 0.062-0.081 mu M, and five additional compounds (8, 11, 16, 18, and 21) exhibited comparable anti-HIV potency. Six DCX analogs (7, 11-12, 18, and 21-22) also showed enhanced selectivity index (SI) values in comparison to the control. Structure-activity relationship (SAR) information suggested that the extended conjugated system of the pyranoxanthone skeleton facilitates the interaction of the small DCX molecule within the viral binding pocket, consequently leading to enhanced anti-HIV activity and selectivity. Compared to DCP compounds, DCX analogs are a more promising new class of anti-HIV agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.025
• 作为产物：
  描述：

  5-溴水杨酸 、 间苯二酚 在 zinc(II) chloride 、 三氯氧磷 作用下， 反应 0.5h， 以79.2%的产率得到7-bromo-1,3-dihydroxy-9H-xanthen-9-one
  参考文献：
  名称：

  Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them

  摘要：

  34 Xanthones were synthesized by microwave assisted technique. Their in vitro inhibition activities against five cell lines growth were evaluated. The SAR has been thoroughly discussed. 7-Bromo-1,3-dihydroxy-9H-xanthen-9-one (3-1) was confirmed as the most active agent against MDA-MB-231 cell line growth with an IC50 of 0.46 +/- 0.03 mu M. Combination of 3-1 and 5,6-dimethylxanthone-4-acetic acid (DMXAA) showed the best synergistic effect. Apoptosis analysis indicated different contributions of early/late apoptosis and necrosis to cell death for both monomers and the combination. Western Blot implied that the combination regulated p53/MDM2 to a better healthy state. Furthermore, 3-1 and DMXAA arrested more cells on G2/M phase; while the combination arrested more cells on S phase. All the evidences support that the 3-1/DMXAA combination is a better anti-cancer therapy. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.068

文献信息

• 一种呫吨酮类化合物及其制备方法和应用
  申请人：广州医科大学

  公开号：CN109369599B

  公开（公告）日：2023-03-24

  本发明涉及一种呫吨酮类化合物及其制备方法和应用，属于药物化学领域。该类化合物的结构如通式I～III所示，本发明的呫吨酮类化合物具有极强的AKR1C3抑制活性和高度的选择性，可应用于制备治疗去势抵抗性前列腺癌的新型药物或治疗醛‑酮还原酶1C3活性相关疾病的药物。
• 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。
• 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 and synthesis of novel xanthone-triazole derivatives as potential antidiabetic agents: α-Glucosidase inhibition and glucose uptake promotion
  作者：Gao-Jie Ye、Tian Lan、Zhi-Xin Huang、Xiao-Ning Cheng、Chao-Yun Cai、Sen-Miao Ding、Min-Li Xie、Bo Wang

  DOI：10.1016/j.ejmech.2019.05.045

  日期：2019.9

  cytotoxicity assays showed that most compounds were low-toxic to human normal hepatocyte cell line (LO2). These novel xanthone triazole derivatives exhibited dual therapeutic effects of α-glucosidase inhibition and glucose uptake promotion, thus they could be use as antidiabetic agents for developing novel drugs against type 2 diabetes.

  抑制碳水化合物分解为葡萄糖或促进葡萄糖转化被认为是2型糖尿病的有效治疗方法。在此，设计，合成了一系列新的黄酮-三唑衍生物，并研究了它们在HepG2细胞中的α-葡萄糖苷酶抑制活性和葡萄糖摄取。与母体化合物a（1,3-二羟基黄酮，IC 50  = 160.8μM）和1-脱氧野oji霉素（阳性对照，IC 50  = 59.5μM）相比，大多数化合物显示出更好的抑制活性。化合物5e是最有效的抑制剂，IC 50值为2.06μM。酶抑制动力学表明，化合物5e，5g，5h，6c，6d，6g和6h是非竞争性抑制剂，分子对接结果与这些化合物与远离活性位点的变构位点结合的非竞争性性质一致（Asp214，Glu276和Asp349）。另一方面，葡萄糖摄取测定显示化合物5e，6a，6c和7g在促进葡萄糖摄取方面表现出高活性。细胞毒性试验表明，大多数化合物对人正常肝细胞系（LO2）均具有低毒性。这些新的蒽酮三唑衍生
• Scope and limitations of the preparation of xanthones using Eaton’s reagent
  作者：JOHANN BOSSON

  DOI：10.55730/1300-0527.3624

  日期：——

  fascinating biological properties. Many synthetic protocols have been developed for the preparation of natural and nonnatural xanthone derivatives. Among them, condensation reactions between salicylic acid derivatives and phenol partners are highly desirable. Those reactions can be satisfactorily performed using Eaton's reagent (P2O5 in CH3SO3H). Despite being highly effective with a variety of substrates,

  氧杂蒽酮包含一大类杂环化合物，具有令人着迷的生物学特性。已经开发了许多合成方案用于制备天然和非天然呫吨酮衍生物。其中，水杨酸衍生物与苯酚伙伴之间的缩合反应是非常理想的。使用 Eaton 试剂（CH3SO3H 中的 P2O5）可以令人满意地进行这些反应。尽管对各种底物都非常有效，但这种方法存在取决于反应前体的电子性质的局限性。本文介绍并讨论了伊顿试剂介导的呫吨酮制备的范围和限制。简而言之，这种方法仅限于利用非常富电子的苯酚底物（如间苯三酚化合物），或在后一种情况下通过分离二苯甲酮中间体来利用富电子的苯酚前体（如间苯二酚衍生物）。贫电子酚不适合​​伊顿试剂的这种转化。