3,6,8-三羟基-1-甲基占吨酮 | 20716-98-7

• 物质功能分类: 天然产物 - 氧杂蒽酮
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 3,6,8-三羟基-1-甲基占吨酮
• 中文别名: 3,6,8-三羟基-1-甲基吨酮；Norlichexanthone;3,6,8-三羟基-1-甲基呫吨酮
• 英文名称: norlichexanthone
• 英文别名: 1,3,6-trihydroxy-8-methylxanthone；1,3,6-trihydroxy-8-methyl-9H-xanthen-9-one；3,6,8-trihydroxy-1-methylxanthone；Nor-lichexanthon；1,3,6-trihydroxy-8-methylxanthen-9-one
• CAS: 20716-98-7
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: AQZHBCDRWFMXIN-UHFFFAOYSA-N

物化性质

• 熔点：
  226-228 °C
• 沸点：
  567.8±49.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3,6,8-三羟基-1-甲基占吨酮 、 硫酸二甲酯 在 potassium carbonate 作用下， 生成 1-羟基-3,6-二甲氧基-8-甲基-9H-氧杂蒽-9-酮
  参考文献：
  名称：

  Aghoramurthy; Seshadri, Journal of Scientific & Industrial Research, 1953, vol. 12B, p. 350,352

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2,4-dioxopentyl)-2,5,7-trihydroxy-2,3-dihydrobenzopyran-4-one 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 22.5h， 以100%的产率得到3,6,8-三羟基-1-甲基占吨酮
  参考文献：
  名称：

  Acylation of multiple anions of poly-.beta.-ketones by hydroxy- and alkoxybenzoates. Cyclization of the resultant tetraketones to benzophenones and xanthones

  摘要：

  DOI：

  10.1021/jo00324a012

文献信息

• Increment of Antimycobaterial Activity on Lichexanthone Derivatives
  作者：Ana Micheletti、Neli Honda、Fernando Pavan、Clarice Leite、Maria Matos、Renata Perdomo、Danielle Bogo、Glaucia Alcantara、Adilson Beatriz

  DOI：10.2174/1573406411309070003

  日期：2013.8.1

  A new dihydropyranexanthone derived from the natural xanthone lichexanthone (1) was synthesised and, together with other 18 derivatives including ω-bromo and ω-aminoalkoxylxanthones (containing methyl, ethyl, propyl, tertbutylamino and piperidinyl moieties), were tested against Mycobacterium tuberculosis. Nine ω-aminoalkoxylxanthones showed good antimycobacterial activity, and their in vitro cytotoxicity was determined using VERO cells in order to calculate the selectivity index (SI). One of these nitrogenated xanthone derivatives showed very promising results, with MIC of 2.6 μM and SI of 48. This MIC is comparable to values found in “first and second line” drugs commonly used to treat TB. In order to understand better about this compound, it was evaluated together with two other ones that showed good SI, against resistant clinical strains of M. tuberculosis to verify the existence of cross-resistance. A chemometrical approach was useful to establish a pattern of antitubercular activity among the group of ω-aminoalkoxylxanthones, according to some structural and chemical features.

  一种从天然黄酮利克黄酮（1）中提取的新型二氢吡喃黄酮被合成出来，并与其他18种衍生物（包括ω-溴和ω-氨基烷氧基黄酮（含有甲基、乙基、丙基、叔丁基氨基和哌啶基部分））一起，针对结核分枝杆菌进行了测试。其中9种ω-氨基烷氧基黄酮显示出良好的抗分枝杆菌活性，并使用VERO细胞测定其体外细胞毒性，以计算选择指数（SI）。其中一种氮化黄酮衍生物显示出非常乐观的结果，MIC为2.6μM，SI为48。该MIC与通常用于治疗结核病的“一线和二线”药物的数值相当。为了更好地了解这种化合物，将其与另外两种显示出良好SI的化合物一起评估，以验证是否存在交叉耐药性。根据一些结构和化学特征，化学计量学方法有助于确定ω-氨基烷氧基黄酮类化合物中的抗结核活性模式。
• Antimycobacterial activity of lichen substances
  作者：N.K. Honda、F.R. Pavan、R.G. Coelho、S.R. de Andrade Leite、A.C. Micheletti、T.I.B. Lopes、M.Y. Misutsu、A. Beatriz、R.L. Brum、C.Q.F. Leite

  DOI：10.1016/j.phymed.2009.07.018

  日期：2010.4

  We describe here the extraction and identification of several classes of phenolic compounds from the lichens Parmotrema dilatatum (Vain.) Hale, Parmotrema tinctorum (Nyl.) Hale, Pseudoparmelia sphaerospora (Nyl.) Hale and Usnea subcavata (Motyka) and determined their anti-tubercular activity. The depsides (atranorin, diffractaic and lecanoric acids), depsidones (protocetraric, salazinic, hypostictic and norstictic acids), xanthones (lichexanthone and secalonic acid), and usnic acid, as well seven orsellinic acid esters, five salazinic acid 8',9'-O-alkyl derivatives and four lichexanthone derivatives, were evaluated for their activity against Mycobacterium tuberculosis. Diffractaic acid was the most active compound (MIC value 15.6 mu g/ml, 41.6 mu M), followed by norstictic acid (MIC value 62.5 mu g/ml, 168 mu M) and usnic acid (MIC value 62.5 mu g/ml, 182 mu M). Hypostictic acid (MIC value 94.0 mu g/ml, 251 mu M) and protocetraric acid (MIC value 125 mu g/ml, 334 mu M) showed moderate inhibitory activity. The other compounds showed lower inhibitory activity on the growth of M. tuberculosis, varying from MIC values of 250 to 1370 mu M. (C) 2009 Elsevier GmbH. All rights reserved.
• Untersuchungen über Flechtenstoffe, XCVIII. Mitteil.: Über Lichexanthon, ein neues Stoffwechselprodukt der Flechte
  作者：Yamhiko Asahina、Hisasi Nogami

  DOI：10.1246/bcsj.17.202

  日期：1942.4
• Xanthone glucoside from an insect pathogenic fungus <i>Conoideocrella luteorostrata</i> NBRC106950
  作者：Tatsuro Yoneyama、Miki Iguchi、Kento Yoshii、Abdelsamed I. Elshamy、Sayaka Ban、Masaaki Noji、Akemi Umeyama

  DOI：10.1080/14786419.2021.1883607

  日期：2022.7.18
• Aghoramurthy; Seshadri, Journal of Scientific & Industrial Research, 1953, vol. 12B, p. 73,75, 350, 351, 352
  作者：Aghoramurthy、Seshadri

  DOI：——

  日期：——