2,7-desoxyosajaxanthone | 36380-18-4

• 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: 2,7-desoxyosajaxanthone
• 英文别名: 5-Hydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one；osajasanthone；5-hydroxy-2,2-dimethylpyrano[3,2-b]xanthen-6(2H)-one；5-Hydroxy-2,2-dimethyl-2H,6H-pyrano<3,2-b>xanthen-6-on；5-hydroxy-2,2-dimethyl-2H-pyrano[3,2-b]xanthen-6-one；5-Hydroxy-2,2-dimethylpyrano[3,2-b]xanthen-6-one；5-hydroxy-2,2-dimethylpyrano[3,2-b]xanthen-6-one
• CAS: 36380-18-4
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: DFUSNNVZHPWEQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2,7-desoxyosajaxanthone 在 potassium carbonate 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 4.0h， 生成 5-(2-Diethylamino-ethylamino)-2,2-dimethyl-2H-pyrano[3,2-b]xanthen-6-one
  参考文献：
  名称：

  Synthesis and cytotoxic activity of 2-dialkylaminoethylamino substituted xanthenone and thioxanthenone derivatives

  摘要：

  The synthesis and biological evaluation of some new pyranoxanthenones and pyranothioxanthenones, substituted with flexible amino side-chains, and their evaluation as potential antitumor agents is described. The cytotoxic activity of the compounds and their eventual selective effect on a phase of the cell cycle were evaluated in vitro, using the murine lymphocytic L1210 leukemia cell line. The new aminoderivatives exhibited highly potent cytotoxicity against the leukemia L1210 cell line when compared to acronycine. All the compounds induced a partial accumulation of cells in the G2 + M phase of the cell cycle. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00068-9
• 作为产物：
  描述：

  3,4-dihydro-5-hydroxy-2,2-dimethyl-2H,6H-pyrano<3,2-b>xanthen-6-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 70.0h， 以90%的产率得到2,7-desoxyosajaxanthone
  参考文献：
  名称：

  Ahluwalia, Vinod K.; Jolly, Ravinder S.; Tehin, Ashok K., Journal of the Chemical Society. Perkin transactions I, 1983, p. 1229 - 1234

  摘要：

  DOI：

文献信息

• Pyranoxanthones: Synthesis, growth inhibitory activity on human tumor cell lines and determination of their lipophilicity in two membrane models
  作者：Carlos M.G. Azevedo、Carlos M.M. Afonso、José X. Soares、Salette Reis、Diana Sousa、Raquel T. Lima、M. Helena Vasconcelos、Madalena Pedro、João Barbosa、Luís Gales、Madalena M.M. Pinto

  DOI：10.1016/j.ejmech.2013.09.012

  日期：2013.11

  The benzopyran and dihydrobenzopyran moieties can be considered as "privileged motifs" in drug discovery being good platforms for the search of new bioactive compounds. These moieties are commonly found fused to the xanthonic scaffold belonging to the biologically important family of the generally designated prenylated xanthones. Several pyranoxanthones have shown promising antitumor activity and since most of them are from natural origin, the biosynthetic pathway only allows a particular pattern of substitution which limits their structural diversity and renders any broad structure activity study hard to be established. Accordingly, with the aim of rationalizing the importance of the fused ring orientation and oxygenation pattern in pyranoxanthones, this study describes the synthesis of 14 new pyranoxanthones and evaluation of their cell growth inhibitory activity in four human tumor cell lines as well as their lipophilicity in two membrane models. This systematic approach allowed establishing structure activity and structure lipophilicity relationships for the obtained compounds in combination with 6 previously described compounds. From this work an angular pyranoxanthone scaffold emerged as particularly promising, presenting a potent cell growth inhibitory activity and suitable drug-like lipophilicity. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Anti-AIDS agents 83. Efficient microwave-assisted one-pot preparation of angular 2,2-dimethyl-2H-chromone containing compounds
  作者：Ting Zhou、Qian Shi、Kuo Hsing Lee

  DOI：10.1016/j.tetlet.2010.06.058

  日期：2010.8

  A novel and efficient microwave-assisted one-pot reaction was developed to synthesize angular 2,2-dimethyl-2H-chromone-containing compounds, which is the first and key step in the synthesis of potent DCK and DCP anti-HIV agents The newly developed microwave synthesis conditions dramatically shortened the reaction time from 2 clays to 4 h with improved yields (c) 2010 Elsevier Ltd All rights reserved