1,2-dihydro-6-hydroxy-3,3-dimethyl-3H,7H-pyrano<2,3-c>xanthen-7-one | 51971-04-1

• 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: 1,2-dihydro-6-hydroxy-3,3-dimethyl-3H,7H-pyrano<2,3-c>xanthen-7-one
• 英文别名: 6-hydroxy-3,3-dimethyl-2,3-dihydropyrano[2,3-c]xanthen-7(1H)-one；1,2-dihydro-6-hydroxy-3,3-dimethyl-3H,7H-pyrano[2,3-c]xanthen-7-one；6-Hydroxy-3,3-dimethyl-1,2-dihydropyrano[2,3-c]xanthen-7-one
• CAS: 51971-04-1
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: NIYOFKHNJSNYPA-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：
  0.28
• 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：

  1,2-dihydro-6-hydroxy-3,3-dimethyl-3H,7H-pyrano<2,3-c>xanthen-7-one 在 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 丙酮 、 苯 为溶剂， 反应 78.0h， 生成 6-methoxy-3,3-dimethyl-3H,7H-pyrano[2,3-c]xanthen-7-one
  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：
• 作为产物：
  描述：

  1-hydroxy-3-(3-methylbut-2-enyloxy)-9H-xanthen-9-one 在 zinc(II) chloride 作用下， 以 邻二甲苯 为溶剂， 反应 20.5h， 以4%的产率得到1,2-dihydro-6-hydroxy-3,3-dimethyl-3H,7H-pyrano<2,3-c>xanthen-7-one
  参考文献：
  名称：

  二羟基黄嘌呤烯丙基化衍生物：对人肿瘤细胞系的合成，结构阐明和生长抑制活性，同时提高了对MCF-7的选择性。

  摘要：

  报道了11种氧杂蒽酮的合成，结构阐明和抗肿瘤活性，这是首次描述的化合物3、4、6-8和9。Xanthones 1和2用作构建基，以获得烯丙基化的衍生物3-8。使用异戊烯基溴化物在碱性介质中进行烯丙基化。通过氧化闭环从化合物4和5获得二氢吡喃黄嘌呤9-11。通过IR，UV，MS和NMR（（1）H，（13）C，COSY，HSQC和HMBC）技术确定化合物的结构，对于化合物4、6和11，通过X确认结构射线晶体学分析。11种氧杂蒽酮对四种人类肿瘤细胞系MCF-7（乳腺癌），NCI-H460（非小细胞肺癌），SF-268（中枢神经系统癌症）体外生长的影响，

  DOI：

  10.1016/j.bmc.2007.06.037

文献信息

• Improved methodologies for synthesis of prenylated xanthones by microwave irradiation and combination of heterogeneous catalysis (K10 clay) with microwave irradiation
  作者：Raquel A.P. Castanheiro、Madalena M.M. Pinto、Sara M.M. Cravo、Diana C.G.A. Pinto、Artur M.S. Silva、Anake Kijjoa

  DOI：10.1016/j.tet.2009.03.019

  日期：2009.5

  been synthesized for the first time by the microwave irradiation method. Prenylation of the xanthone building blocks 1 and 2 with prenyl bromide in alkaline medium, using microwave irradiation, gave the oxyprenylated xanthones 4 and 6, as major products in high yields, as well as diprenylated by-products (5, 7, 8, and 9) in very low yields. Microwave irradiation of oxyprenylated xanthones 4 and 6 furnished

  十一异戊烯化呫吨酮衍生物（4 - 9，11 - 15）已合成的第一次通过微波照射方法。呫吨酮结构单元的异戊二烯化1和2与在碱性介质中的异戊烯基溴，使用微波辐射，得到oxyprenylated呫4和6，作为主要产物以高产率，以及作为副产物（diprenylated 5，7，8，和9）非常低的产量。微波辐射氧炔化的氧杂蒽4和6家具的三个新的重排克莱森产物（11，14，和15），以及先前描述的dihydrofuranoxanthones（12，13）。此外，三个新的（19，20，21）和三个以前的描述（16，17，18）dihydropyranoxanthones也已经从呫制备通过一锅法合成1，2，和3，使用蒙脱土K10粘土作为非均相催化剂，并在各种条件下将蒙脱石K10粘土与微波辐射结合使用。发现溶剂的存在和粘土的类型（商业或干燥的）对产品的收率有很大的影响。这是使用这些方法合成二氢吡喃并蒽酮衍
• 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.