3,3-dimethyl-6-(4-methylphenylsulfonyloxy)-3H,7H-pyrano[2,3-c]xanthen-7-one | 313692-59-0

• 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: 3,3-dimethyl-6-(4-methylphenylsulfonyloxy)-3H,7H-pyrano[2,3-c]xanthen-7-one
• 英文别名: (3,3-Dimethyl-7-oxopyrano[2,3-c]xanthen-6-yl) 4-methylbenzenesulfonate
• CAS: 313692-59-0
• 化学式: C₂₅H₂₀O₆S
• 分子量: 448.496
• InChiKey: ABICKBBUCNAVHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-6-(4-methylphenylsulfonyloxy)-3H,7H-pyrano[2,3-c]xanthen-7-one 在 sodium hydroxide 、 四氧化锇 、 sodium hydride 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 52.25h， 生成 6-methoxy-3,3-dimethyl-1H,2H,3H,7H-pyrano[2,3-c]xanthen-2,7-dione
  参考文献：
  名称：

  Design and synthesis of new pyranoxanthenones bearing a nitro group or an aminosubstituted side chain on the pyran ring. Evaluation of their growth inhibitory activity in breast cancer cells

  摘要：

  Some new 2,6-disubstituted pyrano- and 1,2-dihydropyrano[2,3-c]xanthen-7-ones have been synthesized and their antiproliferative activity has been evaluated against MDA-MB-231 breast cancer cells. The antiproliferative activity evaluation of the compounds provided evidence that a dimethylamino substituted side chain and the presence of 1,2 double bond play a key role in cell growth inhibition. Among the tested derivatives the 6-dimethylaminoethylamino-2-nitropyranoxanthenone analogue possessed a significant inhibitory effect in a wide range of concentrations. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.10.018
• 作为产物：
  描述：

  3-(1,1-dimethylprop-2-ynyloxy)-1-(4-methylphenylsulfonyloxy)-9H-xanthen-9-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以89%的产率得到3,3-dimethyl-6-(4-methylphenylsulfonyloxy)-3H,7H-pyrano[2,3-c]xanthen-7-one
  参考文献：
  名称：

  Design and synthesis of new pyranoxanthenones bearing a nitro group or an aminosubstituted side chain on the pyran ring. Evaluation of their growth inhibitory activity in breast cancer cells

  摘要：

  Some new 2,6-disubstituted pyrano- and 1,2-dihydropyrano[2,3-c]xanthen-7-ones have been synthesized and their antiproliferative activity has been evaluated against MDA-MB-231 breast cancer cells. The antiproliferative activity evaluation of the compounds provided evidence that a dimethylamino substituted side chain and the presence of 1,2 double bond play a key role in cell growth inhibition. Among the tested derivatives the 6-dimethylaminoethylamino-2-nitropyranoxanthenone analogue possessed a significant inhibitory effect in a wide range of concentrations. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.10.018

文献信息

• Design, Synthesis, and Antiproliferative Activity of Some New Pyrazole-Fused Amino Derivatives of the Pyranoxanthenone, Pyranothioxanthenone, and Pyranoacridone Ring Systems:  A New Class of Cytotoxic Agents
  作者：Ioannis K. Kostakis、Prokopios Magiatis、Nicole Pouli、Panagiotis Marakos、Alexios-Leandros Skaltsounis、Harris Pratsinis、Stephane Léonce、Alain Pierré

  DOI：10.1021/jm011117g

  日期：2002.6.1

  these types of compounds is also developed, which resulted in an improvement of the overall yield. The new compounds exhibited interesting cytotoxic activity against the murine leukemia L1210 cell line, being more active than the parent compound, and a number of them possessed cytotoxicity against some human solid tumor cell lines. Especially in the case of a colon adenocarcinoma cell line, their IC(50)

  已经设计并合成了一系列新颖的吡喃并蒽酮，吡喃并噻吨酮和吡喃ac啶酮作为as啶酮生物碱丙烯醛酸的类似物，并且已经研究了它们的DNA结合和体外细胞毒性。通过使相应的6-甲苯磺酸酯5a-e与2-羟乙基肼反应，然后将取代的乙醇6a-e的游离羟基转化为相应的甲磺酸酯，得到标题化合物，然后将其用适当取代的仲胺进行处理。提供目标导数8-27。还开发了用于制备这些类型化合物的替代合成方法，这导致了总产率的提高。新化合物对鼠白血病L1210细胞系表现出令人感兴趣的细胞毒活性，它比母体化合物具有更高的活性，并且其中许多具有对某些人类实体瘤细胞系的细胞毒性。特别是在结肠腺癌细胞系的情况下，它们的IC（50）值与米托蒽醌相当。这项研究的结果表明，将氨基取代的吡唑环并入丙烯醛发色团或等排体中，可以提高先导化合物的活性，因此，它可能在寻找新的抗癌药中有用。源自这种天然产物的药物。
• Synthesis and cytotoxic activity of 2-dialkylaminoethylamino substituted xanthenone and thioxanthenone derivatives
  作者：Ioannis Kostakis、Konstantinos Ghirtis、Nicole Pouli、Panagiotis Marakos、Alexios-Leandros Skaltsounis、Stephane Leonce、Daniel H Caignard、Ghanem Atassi

  DOI：10.1016/s0014-827x(00)00068-9

  日期：2000.7

  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.
• Design and synthesis of new pyranoxanthenones bearing a nitro group or an aminosubstituted side chain on the pyran ring. Evaluation of their growth inhibitory activity in breast cancer cells
  作者：George Kolokythas、Ioannis K. Kostakis、Nicole Pouli、Panagiotis Marakos、Olga Ch. Kousidou、George N. Tzanakakis、Nikos K. Karamanos

  DOI：10.1016/j.ejmech.2006.10.018

  日期：2007.3

  Some new 2,6-disubstituted pyrano- and 1,2-dihydropyrano[2,3-c]xanthen-7-ones have been synthesized and their antiproliferative activity has been evaluated against MDA-MB-231 breast cancer cells. The antiproliferative activity evaluation of the compounds provided evidence that a dimethylamino substituted side chain and the presence of 1,2 double bond play a key role in cell growth inhibition. Among the tested derivatives the 6-dimethylaminoethylamino-2-nitropyranoxanthenone analogue possessed a significant inhibitory effect in a wide range of concentrations. (c) 2006 Elsevier Masson SAS. All rights reserved.