1-hydroxy-6-(2-oxiranylmethoxy) xanthone

• 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-hydroxy-6-(2-oxiranylmethoxy) xanthone
• 英文别名: 6-(2,3-epoxypropoxy)-1-hydroxyxanthone；6-(2,3-epoxypropoxy)-1-hydroxyxanthen-9-one；1-hydroxy-6-(oxiran-2-ylmethoxy)xanthen-9-one
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: YORFTLUAKBODKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-hydroxy-6-(2-oxiranylmethoxy) xanthone 、 、 N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(1-hydroxy-9-oxoxanth-6-yloxy)propanamine hydrochloride 以 乙醇 为溶剂， 以3,912,733, and 2-aminotetralin (1.49 g) in absolute ethanol (40 ml), N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(1-hydroxy-9-oxoxanth-6-yloxy)propanamine hydrochloride is obtained ((i)的产率得到1,2,3,4-四氢-2-萘胺
  参考文献：
  名称：

  Aryloxypropanolaminotetralins, a process for their preparation and

  摘要：

  本文描述了具有β-拮抗活性的Aryloxypropanolaminotetralins的化学式，其中R是氢、羟基或甲氧基，Ar是可选取代的芳香族或杂环芳香族基，以光学活性或不活性形式存在，以及它们的酸加成盐。还描述了它们的制备过程和含有化合物(i)或它们的药用可接受的酸加成盐的制药组合物。

  公开号：

  US05254595A1
• 作为产物：
  描述：

  2,6-二羟基苯甲酸 在 PPA 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-hydroxy-6-(2-oxiranylmethoxy) xanthone
  参考文献：
  名称：

  Synthesis and pharmacological activities of xanthone derivatives as α-glucosidase inhibitors

  摘要：

  Considerable interest has been attracted in xanthone and its derivatives because of their large variety of pharmacological activities. In this project, a series of hydroxylxanthones and their aectoxy and alkoxy derivatives were synthesized and evaluated as alpha-glucosidase inhibitors, aimed at clarifying the structure-activity correlation. The results indicated that these xanthone derivatives were capable of inhibiting in vitro alpha-glucosidase with moderate to good activities. Among them, polyhydroxylxanthones exhibited the highest activities and thus may be exploitable as a lead compound for the development of potent alpha-glucosidase inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.014

文献信息

• γ-Pyrone Compounds as Potential Anti-cancer Drugs
  作者：Shorong-Shii Liou、Wen-Liang Shieh、Tien-Hsiang Cheng、Shen-Jeu Won、Chun-Nan Lin

  DOI：10.1111/j.2042-7158.1993.tb05686.x

  日期：2011.4.12

  The γ-pyrones, artomunoxanthotrione epoxide, cyclocommunol, cyclomulberrin, and cyclocommunin exhibited potent inhibition of human PLC/PRF/5 and KB cells in-vitro. Dihydroisocycloartomunin showed significant and potent inhibition of human PLC/PRF/5 and KB cells in-vitro, respectively. Cyclomorusin, dihydrocycloartomunin and artomunoxanthone showed significant inhibition of KB cells in-vitro. Based on the above finding and the reported antileukaemic activity of xanthone psorospermin, a series of natural γ-pyrones was prepared and the inhibition of human PLC/PRF/5 and KB cells in-vitro was measured. Structure-activity analysis indicated the epoxide group substituted at 3-hydroxyl and 2,6-; 3,6-; and 3,5-dihydroxyl xanthone enhanced the anti-tumour activity. The epoxide group substituted at the 6-hydroxyl group of 1,6-dihydroxyxanthone did not show anti-tumour activity.

  γ-吡喃酮类化合物，包括artomunoxanthotrione环氧化物、cyclocommunol、cyclomulberrin和cyclocommunin在体外表现出对人类PLC/PRF/5和KB细胞的强效抑制作用。Dihydroisocycloartomunin在体外对人类PLC/PRF/5和KB细胞分别表现出显著和强效的抑制作用。Cyclomorusin、dihydrocycloartomunin和artomunoxanthone在体外对KB细胞表现出显著的抑制作用。基于上述发现和报道的黄酮类化合物psorospermin的抗白血病活性，制备了一系列天然γ-吡喃酮类化合物，并测量了其在体外对人类PLC/PRF/5和KB细胞的抑制作用。结构活性分析表明，取代3-羟基和2,6-；3,6-；和3,5-二羟基黄酮的环氧化物基团增强了抗肿瘤活性。1,6-二羟基黄酮的6-羟基处取代的环氧化物基团没有显示出抗肿瘤活性。
• Cytotoxic Activity and DNA-Binding Properties of Isoeuxanthone Derivatives
  作者：Hui Fang Wang、Hong Yan、Xianghua Gao、Baolong Niu、Ruijie Guo、Liqiao Wei、Bingshe Xu、Ning Tang

  DOI：10.1248/cpb.c13-00789

  日期：——

  (HepG2) were used to evaluate the cytotoxic activities of xanthone derivatives by acid phosphatase assay. Analyses showed that the oxiranylmethoxy substituted xanthone exhibited more effective cytotoxic activity against the cancer cells than the other substituted xanthones. The effects on the inhibition of tumor cells in vitro agreed with the studies of DNA-binding.

  在这项研究中，通过分光光度法和粘度测量研究了不同基团取代的异异黄酮衍生物与小牛胸腺DNA（ct DNA）的相互作用。结果表明，x吨酮衍生物可以通过an吨酮环的平面插入DNA碱基对中，并且根据计算的猝灭常数值，各种取代基可能影响与DNA的结合亲和力。此外，包括人宫颈癌细胞系（HeLa）和人肝细胞肝癌细胞系（HepG2）在内的两种肿瘤细胞系被用于通过酸性磷酸酶测定来评估x吨酮衍生物的细胞毒活性。分析表明，氧杂氧基甲氧基取代的蒽酮对癌细胞具有比其他取代的氧杂蒽酮更有效的细胞毒活性。
• Compounds for the treatment of hepatoma
  申请人：National Science Council

  公开号：US05741813A1

  公开（公告）日：1998-04-21

  Compounds of general Formula I in which the substituents of R.sub.1 -R.sub.7 are hydrogen, hydroxy group, C.sub.1-6 alkyl group, C.sub.1-6 alkoxy group, or epoxypropoxy, but at the most, six of the substituents can simultaneously be hydrogen, methoxy group, or hydroxy group, or epoxypropoxy group for activity against hepatoma. There are also described processes for the preparation of the novel compounds and useful intermediates. Substitute benzophenones are described.

  通式I的化合物中，R.sub.1-R.sub.7的取代基为氢、羟基、C.sub.1-6烷基、C.sub.1-6烷氧基或环氧丙氧基，但最多只有六个取代基可以同时为氢、甲氧基或羟基，或环氧丙氧基，用于对抗肝癌的活性。还描述了制备新化合物和有用中间体的过程。还描述了取代苯甲酮。
• Aryloxypropanolaminotétralines, un procédé pour leur préparation et composés pharmaceutiques les contenant
  申请人：ELF SANOFI

  公开号：EP0375560B1

  公开（公告）日：1993-05-12
• US5254595A
  申请人：——

  公开号：US5254595A

  公开（公告）日：1993-10-19