3-hydroxy-1,5-dimethoxy-9H-xanthen-9-one | 61243-74-1

• 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-hydroxy-1,5-dimethoxy-9H-xanthen-9-one
• 英文别名: 1,5-dimethoxy-3-hydroxyxanthone；3-hydroxy-1,5-dimethoxy-xanthen-9-one；3-hydroxy-1,5-dimethoxyxanthen-9-one
• CAS: 61243-74-1
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: FSKPYZDVBCJCQC-UHFFFAOYSA-N

物化性质

• 沸点：
  483.7±45.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1,5-dimethoxy-9H-xanthen-9-one 在 吡啶 、 溴 、 溶剂黄146 作用下， 反应 21.0h， 生成 5,10-dimethoxy-2-isopropenyl-6H-furo<2,3-c>xanthen-6-one
  参考文献：
  名称：

  角型呋喃喃酮，脱氧去氢皮精胺甲基醚（5,10-二甲氧基-2-异丙烯基-6 H-呋喃[2,3 - c ]黄嘌呤-6-一）的合成

  摘要：

  异丙烯基亚硫酸铜与4-溴-1,5-二甲氧基-3-羟基蒽酮的反应合成了角化异丙烯基呋喃酮蒽杂环体系，抗白血病天然产物psorospermin以此为基础。

  DOI：

  10.1002/jhet.5570230338
• 作为产物：
  描述：

  2,3-二甲氧基苯甲酸 在 氢氧化钾 、 水 、 乙酸酐 、 zinc(II) chloride 、 silver(l) oxide 、 三氯氧磷 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 34.33h， 生成 3-hydroxy-1,5-dimethoxy-9H-xanthen-9-one
  参考文献：
  名称：

  角型呋喃喃酮，脱氧去氢皮精胺甲基醚（5,10-二甲氧基-2-异丙烯基-6 H-呋喃[2,3 - c ]黄嘌呤-6-一）的合成

  摘要：

  异丙烯基亚硫酸铜与4-溴-1,5-二甲氧基-3-羟基蒽酮的反应合成了角化异丙烯基呋喃酮蒽杂环体系，抗白血病天然产物psorospermin以此为基础。

  DOI：

  10.1002/jhet.5570230338

文献信息

• Synthesis and pharmacological evaluation of new methyloxiranylmethoxyxanthone analogues
  作者：Sangwook Woo、Da-hye Kang、Jung Min Nam、Chong Soon Lee、Eun-Mi Ha、Eung-Seok Lee、Youngjoo Kwon、Younghwa Na

  DOI：10.1016/j.ejmech.2010.06.017

  日期：2010.9

  etoposide at 100 μM concentration. In the DNA cross-linking test, compounds 20, 30 and 31 produced DNA cross-linked adducts and compound 30 was the strongest DNA cross-linker. Based on the combined pharmacological results, we suspected that the strong anti-cancer activity of compounds 16, 17, 20, 30 and 31 originated from the DNA mono-alkylation or cross-linking properties of the compounds.

  为了开发对拓扑异构酶II和DNA起作用的潜在抗癌药，我们合成了12种新的黄酮酮衍生物。在细胞毒性测试中，化合物17和31对大多数测试的癌细胞系的抑制活性比阿霉素强2至7倍。卤代醇基团拴化合物19，21和27显示出相当的拓扑异构酶II依托泊苷抑制活性，在100μM浓度。在DNA交联测试中，化合物20，30和31产生的DNA交联的加合物和化合物30是最强的DNA交联剂。基于组合的药理学结果，我们怀疑化合物的强的抗肿瘤活性16，17，20，30和31源自所述化合物的DNA的单烷基化或交联性能。
• 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
  作者：Ting Zhou、Emika Ohkoshi、Qian Shi、Kenneth F. Bastow、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2012.03.037

  日期：2012.5

  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.
• Conformationally Restricted Analogues of Psorospermin:  Design, Synthesis, and Bioactivity of Natural-Product-Related Bisfuranoxanthones
  作者：Robert A. Heald、Thomas S. Dexheimer、Hariprasad Vankayalapati、Adam Siddiqui-Jain、Lajos Z. Szabo、Mary C. Gleason-Guzman、Laurence H. Hurley

  DOI：10.1021/jm049299c

  日期：2005.4.1

  The antileukemic xanthone psorospermin is a topoisomerase II-dependent DNA alkylator in advanced preclinical. development. Efforts have been made to further understand the structural requirements of its mechanism of action through the synthesis of ring-constrained analogues, based on the skeleton of the bisfuranoxanthone natural products. Molecules were designed that contain the bisfuran and xanthone portions of naturally occurring psorofebrins, and molecular modeling was used to assess their DNA alkylating potential and to refine the structures. A short, diastereoselective synthetic process to access bisfuranoxanthones was developed, culminating in the first total synthesis of (+/-)-isohydroxypsorofebrin. Two compounds designed and synthesized were of particular interest, chlorohydrin 7 and epoxide 6, which are reactive analogues of the natural product isohydroxypsorofebrin. The chlorohydrin retains the psorospermin-like DNA alkylation characteristics despite its rigid structure and high innate affinity for DNA. Molecular modeling has been used to rationalize the increased activity of the chlorohydrin. The chlorohydrin and epoxide show increased cytotoxicity compared to isohydroxypsorofebrin against a range of human tumor cell lines.
• US7244760B2
  申请人：——

  公开号：US7244760B2

  公开（公告）日：2007-07-17
• Synthesis of the angular furanoxanthone, deoxydehydropsorospermin methyl ether (5,10-dimethoxy-2-isopropenyl-6<i>H</i>-furo[2,3-<i>c</i>]xanthen-6-one)
  作者：Ralph T. Scannell、Robert Stevenson

  DOI：10.1002/jhet.5570230338

  日期：1986.5

  The angular isopropenylfuranoxanthone heterocyclic system, on which the anti-leukemic natural product psorospermin is based, is synthesized by the reaction of cuprous isopropenylacetylide with 4-bromo-1,5-dimethoxy-3-hydroxyxanthone.

  异丙烯基亚硫酸铜与4-溴-1,5-二甲氧基-3-羟基蒽酮的反应合成了角化异丙烯基呋喃酮蒽杂环体系，抗白血病天然产物psorospermin以此为基础。