griseoxanthone C | 3569-83-3

• 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: griseoxanthone C
• 英文别名: 1,6-dihydroxy-3-methoxy-8-methylxanthone；1,6-dihydroxy-3-methoxy-8-methyl-9H-xanthen-9-one；1,6-dihydroxy-3-methoxy-8-methylxanthen-9-one
• CAS: 3569-83-3
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: UIKVQKMDLQHSKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  griseoxanthone C 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以61%的产率得到3-O-methylthiophanic acid
  参考文献：
  名称：

  Elix, John A.; Crook, Caroline E.; Jiang, Hui, Australian Journal of Chemistry, 1992, vol. 45, # 5, p. 845 - 855

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-dihydroxy-7-methoxy-2-(2,4-dioxopentyl)-2,3-dihydro-4H-1-benzopyran-4-one 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以80%的产率得到griseoxanthone C
  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

• Dienone-phenol rearrangement of (+)-2'-demethoxydehydrogriseofulvin into a 4-methylxanthone derivative.
  作者：TAIKO ODA、YUKO YAMAGUCHI、YOSHIHIRO SATO

  DOI：10.1248/cpb.34.858

  日期：——

  Treatment of (+)-2'-demethoxydehydrogriseofulvin (2b) with magnesium iodide afforded 5-chloro-2, 8-dihydroxy-6-methoxy-4-methylxanthone (3a) via dienone-phenol rearrangement. The structure of 3a was determined by means of a carbon-13 nuclear magnetic resonance (13C-NMR) long-range selective proton decoupling (LSPD) experiment performed on its diacetate 3b. The rearrangement of 2b was also effected with p-toluenesulfonic acid to give 5-chloro-6, 8-dimethoxy-2-hydroxy-4-methylxanthone (6a). On the other hand, reaction of (-)-dehydrogriseofulvin (2d) with p-toluenesulfonic acid under more vigorous conditions resulted in racemization, no rearrangement being observed.

  对(+)-2'-去甲氧基去氟酮（2b）与碘化镁反应，通过烯酮-酚重排生成了5-氯-2, 8-二羟基-6-甲氧基-4-甲基黄烷酮（3a）。3a的结构通过对其二醋酸酯3b进行的碳-13核磁共振（13C-NMR）长程选择性质子去耦实验确定。使用对苯磺酸处理2b也实现了重排，生成了5-氯-6, 8-二甲氧基-2-羟基-4-甲基黄烷酮（6a）。另一方面，(-)-去氟酮（2d）与对苯磺酸在更强烈的条件下反应，导致了外消旋化，没有观察到重排。
• 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。
• A prenylated acridone alkaloid and ferulate xanthone from barks of <i>Citrus medica</i> (Rutaceae)
  作者：Marie Fomani、Emmanuel Ngeufa Happi、Kouam、Poree Francois-Hugues、Marie-Christine Lallemand、Alain François Kamdem Waffo、Jean Duplex Wansi

  DOI：10.1515/znb-2014-0179

  日期：2015.1.1

  A new prenylated acridone alkaloid, medicacridone (1), and a new ferulate xanthone, medicaxanthone (5), together with 11 known compounds were isolated from the methanol extract of the bark of the Cameroonian medicinal plant Citrus medica. The structures of all compounds were determined by comprehensive analyses of their 1D and 2D NMR, mass spectral (EI and ESI) data, chemical reactions, and comparison with previously known analogues. The agar diffusion test delivered low to missing antimicrobial activities, corresponding with MICs > 1 mg mL^–1, while compounds 1–6 and atalantoflavone (9) displayed weak cytotoxic activity against the human Caucasian prostate adenocarcinoma cell line PC-3, with IC₅₀ values ranging from 60.5 to 80.0 μm versus doxorubicine with IC₅₀=0.9 μm.

  摘要：从喀麦隆药用植物柚子(Citrus medica)的树皮甲醇提取物中分离出一种新的异戊二烯基喹啉生物碱medicacridone(1)和一种新的ferulate黄酮medicaxanthone(5)，以及11种已知化合物。通过对它们的1D和2D NMR、质谱(EI和ESI)数据、化学反应和与先前已知的类似物的比较进行全面分析，确定了所有化合物的结构。琼脂扩散试验显示抗微生物活性低或缺失，相应的最小抑菌浓度(MICs)大于1 mg mL^–1，而化合物1-6和atalantoflavone(9)对人类高加索前列腺腺癌细胞系PC-3显示出较弱的细胞毒性活性，IC₅₀值在60.5到80.0 μm范围内，与doxorubicin的IC₅₀=0.9 μm相比。
• 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.
• Elix, John A.; Crook, Caroline E.; Jiang, Hui, Australian Journal of Chemistry, 1992, vol. 45, # 5, p. 845 - 855
  作者：Elix, John A.、Crook, Caroline E.、Jiang, Hui、Zhi-ning, Zhu

  DOI：——

  日期：——