1,2-dihydroxyxanthone | 17623-69-7

• 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-dihydroxyxanthone
• 英文别名: 1,2-dihydroxy-9H-xanthen-9-one；1,2-Dihydroxyxanthon；Dioxyxanthon；1,2-dihydroxyxanthen-9-one
• CAS: 17623-69-7
• 化学式: C₁₃H₈O₄
• 分子量: 228.204
• InChiKey: XDBLKQQNHFWWHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-dihydroxyxanthone 生成 1,2-dimethoxy-9H-xanthen-9-one
  参考文献：
  名称：

  Davies et al., Journal of the Chemical Society, 1958, p. 1790,1793

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 sodium hydroxide 、 三氯化铝 、 铜 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 甲苯 为溶剂， 反应 132.0h， 生成 1,2-dihydroxyxanthone
  参考文献：
  名称：

  摘要：

  The synthesis, structure elucidation, and biological activities of five isomeric xanthonolignoids. (+/-)-trans-kielcorin C, (+/-)-cis-kielcorin C, (+/-)-trans-kielcorin D, (+/-)-trans-isokielcorin D. and (+/-)-trans-kielcorin E, are reported. The synthetic approach is based on the oxidative coupling of coniferyl alcohol with an appropriate xanthone. The influence of different oxidizing agents was studied, and the best results were obtained with potassium hexacyanoferrate(III). The structure elucidation was achieved by 2D-NMR techniques such as COSY, HETCOR, HSQC, and HMBC. Long-range C,H connectivities were used to establish the orientation of the substituents on the 1,4-dioxine rings, while NOE experiments were used to determine the confil-urations of these rings. These xanthonolignoids. as well as (+/-)-trans-kielcorin, (+/-)-trans-kielcorin B, (+/-)-trans-isokielcorin B. and the xanthonic building blocks 3,4-. 1,2-, and 2.3-dihydroxy-9H-xanthen-9-ones. and 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one. were evaluated for their in vitro effect on the growth of three human cancer cell lines, MCF-7 (breast), TK-10 (renal), and UACC-62 (melanoma), and on the proliferation of human lymphocytes.

  DOI：

  10.1002/1522-2675(200209)85:9<2862::aid-hlca2862>3.0.co;2-r

文献信息

• Efficacy, Stability, and Safety Evaluation of New Polyphenolic Xanthones Towards Identification of Bioactive Compounds to Fight Skin Photoaging
  作者：Diana I. S. P. Resende、Mariana C. Almeida、Bruna Maciel、Helena Carmo、José Sousa Lobo、Carlotta Dal Pozzo、Sara M. Cravo、Gonçalo P. Rosa、Aida Kane-Pagès、Maria do Carmo Barreto、Isabel F Almeida、Maria Emília de Sousa、Madalena M. M. Pinto

  DOI：10.3390/molecules25122782

  日期：——

  stress, making the search for new antioxidant compounds highly desirable in this field. Naturally occurring xanthones are polyphenolic compounds that can be found in microorganisms, fungi, lichens, and some higher plants. This class of polyphenols has a privileged scaffold that grants them several biological activities. We have previously identified simple oxygenated xanthones as promising antioxidants

  抗氧化剂长期以来一直用于化妆品行业，以防止由氧化应激介导的皮肤光老化，这使得该领域非常需要寻找新的抗氧化剂化合物。天然存在的氧杂蒽酮是多酚化合物，可以在微生物、真菌、地衣和一些高等植物中找到。这类多酚具有特殊的支架，赋予它们多种生物活性。我们之前已将简单的含氧氧杂蒽酮确定为有前途的抗氧化剂，并披露为命中的 1,2-二羟基氧杂蒽酮 (1)。在此，我们合成并研究了具有不同多氧化模式的氧杂蒽酮作为皮肤抗光老化成分的潜力。在 DPPH 抗氧化试验中，两种新合成的衍生物的 IC50 值与抗坏血酸的范围相同。合成的呫吨酮被发现是极好的酪氨酸酶抑制剂和弱至中度的胶原酶和弹性蛋白酶抑制剂，但没有显示针对透明质酸酶的活性。表征了它们的金属螯合效应（FeCl3 和 CuCl2）以及它们在不同 pH 值下的稳定性，以了解它们作为未来化妆品活性剂的潜力。在合成的聚氧化氧杂蒽酮中，1,2-二羟基氧杂蒽酮 (1) 被
• Xanthone analogs for treating infectious diseases and complexation of heme and porphyrins
  申请人：——

  公开号：US20020055644A1

  公开（公告）日：2002-05-09

  Therapeutic compounds and compositions for the treatment of infectious diseases are disclosed. The compounds are xanthones and xanthone derivatives, such as 3,5-bis-&egr;-(N,N-diethylamino)amyloxyxanthone. The described compositions include such compounds and a pharmaceutical carrier. These compositions also can include additional materials conventionally used to form therapeutic compositions. 3,5-bis-&egr;-(N,N-diethylamino)amyloxyxanthone has an IC 50 for Plasmodium falciparum of about 0.15 &mgr;M, and an IC 50 for Leishmania mexicana of <<0.5 &mgr;M. These compositions are additionally useful for forming soluble complexes with heme and porphyrins.

  本文披露了用于治疗传染病的治疗化合物和组合物。这些化合物是黄酮和黄酮衍生物，例如3,5-双-&egr;-(N,N-二乙基氨基)戊氧基黄酮。所述组合物包括这些化合物和药用载体。这些组合物还可以包括传统用于形成治疗组合物的其他材料。3,5-双-&egr;-(N,N-二乙基氨基)戊氧基黄酮在恶性疟原虫的IC50约为0.15 &mgr;M，在墨西哥利什曼原虫的IC50为<<0.5 &mgr;M。这些组合物还可用于形成与血红素和卟啉的可溶性复合物。
• Agent for inhibiting binding of 5 alpha -dihydrotestosterone with androgen receptor as well as process for obtaining same
  申请人：Kabushiki Kaisha Vitamin Kenkyusyo

  公开号：EP0296625A2

  公开（公告）日：1988-12-28

  An agent for inhibiting the binding of 5α-dihydrotestosterone with androgen receptor. which comprises at least one extract from herbs or one of specific xanthone compounds, and a process for obtaining the agent.

  一种抑制 5α-二氢睾酮与雄激素受体结合的制剂，它包括至少一种草药提取物或一种特定的黄酮化合物，以及获得该制剂的工艺。
• [EN] CYTOTOXIC XANTHONE COMPOUNDS<br/>[FR] COMPOSÉS DE XANTHONE CYTOTOXIQUE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2009036106A1

  公开（公告）日：2009-03-19

  The present invention relates to xanthone compounds isolated from the plant Psorospermum molluscum Hochr. (Clusiaceae), a Madagascar plant, which are potent cytotoxic agents.

  本发明涉及从马达加斯加植物Psorospermum molluscum Hochr. (Clusiaceae)中分离出的番木鳖素类化合物，这些化合物是强有力的细胞毒剂。
• 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.