6-methoxy-3,3-dimethyl-3H,7H-pyrano[2,3-c]xanthen-7-one | 36380-19-5

• 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: 6-methoxy-3,3-dimethyl-3H,7H-pyrano[2,3-c]xanthen-7-one
• 英文别名: 6-Methoxy-3,3-dimethylpyrano[2,3-c]xanthen-7-one
• CAS: 36380-19-5
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: UBMLFAVZXWPOAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methoxy-3,3-dimethyl-3H,7H-pyrano[2,3-c]xanthen-7-one 在 4-二甲氨基吡啶 、 potassium osmate(VI) dihydrate 、 N-溴代丁二酰亚胺(NBS) 、 (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 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 (1R,2R)-(-)-dicamphanoyl-3,3-dimethyl-5-bromo-6-methoxy-1,2-dihydropyrano[2,3-c]xanthen-7(1H)-one
  参考文献：
  名称：

  Anti-AIDS agents 89. Identification of DCX derivatives as anti-HIV and chemosensitizing dual function agents to overcome P-gp-mediated drug resistance for AIDS therapy

  摘要：

  In this study, 19 dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-dihydropyranoxanth-one (DCX) derivatives, previously discovered as novel anti-HIV agents, were evaluated for their potential to reverse multi-drug resistance (MDR) in a cancer cell line over-expressing P-glycoprotein (P-gp). Seven compounds fully reversed resistance to vincristine (VCR) at 4 mu M, a 20-fold enhancement compared to the first generation chemosensitizer, verapamil (4 mu M). The mechanism of action of DCPs and DCXs was also resolved, since the most active compounds (3, 4, and 7) significantly increased intracellular drug accumulation due, in part, to inhibiting the P-gp mediated drug efflux from cells. We conclude that DCPs (3 and 4) and DCXs (7, 11, and 17) can exhibit polypharmacologic behavior by acting as dual inhibitors of HIV replication and chemoresistance mediated by P-gp. As such, they may be useful in combination therapy to overcome P-gp-associated drug resistance for AIDS treatment. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.037
• 作为产物：
  描述：

  夫拉美诺 在 吡啶 、 Eaton’s reagent 作用下， 生成 6-methoxy-3,3-dimethyl-3H,7H-pyrano[2,3-c]xanthen-7-one
  参考文献：
  名称：

  Anti-AIDS agents 89. Identification of DCX derivatives as anti-HIV and chemosensitizing dual function agents to overcome P-gp-mediated drug resistance for AIDS therapy

  摘要：

  In this study, 19 dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-dihydropyranoxanth-one (DCX) derivatives, previously discovered as novel anti-HIV agents, were evaluated for their potential to reverse multi-drug resistance (MDR) in a cancer cell line over-expressing P-glycoprotein (P-gp). Seven compounds fully reversed resistance to vincristine (VCR) at 4 mu M, a 20-fold enhancement compared to the first generation chemosensitizer, verapamil (4 mu M). The mechanism of action of DCPs and DCXs was also resolved, since the most active compounds (3, 4, and 7) significantly increased intracellular drug accumulation due, in part, to inhibiting the P-gp mediated drug efflux from cells. We conclude that DCPs (3 and 4) and DCXs (7, 11, and 17) can exhibit polypharmacologic behavior by acting as dual inhibitors of HIV replication and chemoresistance mediated by P-gp. As such, they may be useful in combination therapy to overcome P-gp-associated drug resistance for AIDS treatment. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.037

文献信息

• Design and synthesis of some new pyranoxanthenones with cytotoxic activity
  作者：Konstantinos Ghirtis、Nicole Pouli、Panagiotis Marakos、Alexios-Leandros Skaltsounis、Stephane Leonce、Ghanem Atassi、Daniel H. Caignard

  DOI：10.1002/jhet.5570380121

  日期：2001.1

  As part of a research program directed towards the design and synthesis of pyranoxanthones structurally related to acronycine, we present here the synthesis and cytotoxic activity of the pyranoxanthones 3 and 4 (X= H, Br; R= H, OMe; R'= H, Ac). Some of these compounds inhibit L1210 cell proliferation.

  作为针对设计和合成与丙烯醛相关的吡喃黄嘌呤的研究计划的一部分，我们在此介绍吡喃黄嘌呤3和4的合成和细胞毒活性（X = H，Br； R = H，OMe； R'= H ，交流）。这些化合物中的一些抑制L1210细胞增殖。
• Concise Synthesis of Chromene/Chromane-Type Aryne Precursors and Their Applications
  作者：Yuan-Ze Xu、Jia-Wei Tian、Feng Sha、Qiong Li、Xin-Yan Wu

  DOI：10.1021/acs.joc.1c00493

  日期：2021.5.7

  The gram-scale synthesis of 5,6-, 6,7-, and 7,8-chromene/chromane-type aryne precursors and their applications in regioselective transformation to other functional derivatives is reported. Chromene/chromane-type arynes are generated under mild conditions, which can further undergo [2 + 2], [3 + 2], and [4 + 2] cycloaddition reactions, nucleophilic addition reactions, and σ-insertion reactions to produce

  报道了5,6-，6,7-和7,8-亚甲基/苯并二氢吡喃型芳烃前体的克级合成及其在向其他功能衍生物的区域选择性转化中的应用。Chromene / chromane型芳烃是在温和条件下产生的，可以进一步进行[2 + 2]，[3 + 2]和[4 + 2]环加成反应，亲核加成反应和σ插入反应，从而产生结构新颖的取代的色烯和苯并二氢吡喃。在三键邻位的含氧引导基团促进了反应的优异区域选择性，该基团可以被除去或切换成其他官能团，包括烯基，芳基，杂芳基和芳基氨基。
• Acronycine Analog: New Selective Synthesis of 6‐Methoxy‐3,3‐dimethyl‐3H,7H‐pyrano[2,3‐c]xanthen‐7‐one
  作者：B. Serge Kirkiacharian、Bernardin Akagah

  DOI：10.1080/00397910701861024

  日期：2008.3.1

  Abstract A new, convenient, and selective route to the dimethylpyrano[2,3‐c]xanthen‐7‐one, analog of acronycine, via aromatization and dehydrogenation reactions from the corresponding saturated hexahydro intermediate is described.

  摘要描述了通过芳构化和脱氢反应从相应的饱和六氢中间体制备二甲基吡喃并 [2,3-c]xanthen-7-one，即 acronycine 类似物的一种新的、方便的和选择性的途径。
• 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
  作者：Ting Zhou、Qian Shi、Chin-Ho Chen、Li Huang、Phong Ho、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1016/j.ejmech.2011.10.025

  日期：2012.1

  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.
• Synthesis and Conformational Analysis of Some New Pyrano[2,3-c]xanthen-7-one and Pyrano[3,2-b]xanthen-6-one Derivatives with Cytotoxic Activity
  作者：Panagiotis Marakos、Konstantinos Ghirtis、Nicole Pouli、Alexios-Leandros Skaltsounis、Stephane Leonce、Daniel H. Caignard、Ghanem Atassi

  DOI：10.3987/com-99-8727

  日期：——