6,8-dihydroxy-3,4-benzoxanthen-9-one | 53865-02-4

• 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: 6,8-dihydroxy-3,4-benzoxanthen-9-one
• 英文别名: 8,10‐dihydroxy‐7H‐benzo[c]xanthen‐7‐one；1,3-Dihydroxy-5,6-benzoxanthon；8,10-dihydroxy-7H-benzo[c]xanthen-7-one；8,10-dihydroxy-benzo[c]xanthen-7-one；8,10-dihydroxybenzo[c]xanthen-7-one
• CAS: 53865-02-4
• 化学式: C₁₇H₁₀O₄
• mdl: MFCD13969027
• 分子量: 278.264
• InChiKey: OMSPMYABSZAPJV-UHFFFAOYSA-N

物化性质

• 沸点：
  577.2±30.0 °C(Predicted)
• 密度：
  1.507±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• 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

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  6,8-dihydroxy-3,4-benzoxanthen-9-one 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.0h， 生成 10-(benzyloxy)-7-oxo-7H-benzo[c]xanthen-8-yl 4-fluorobenzoate
  参考文献：
  名称：

  合成新型苯并蒽酮类似物作为非喜树碱拓扑异构酶I抑制剂。

  摘要：

  铅化合物苯并an吨酮侧链的结构修饰提供了一系列苯并an吨酮类似物，其中首次报道了其中的12个。结果表明，这些化合物中的大多数对肿瘤细胞具有中等的细胞毒性，在微摩尔范围内的抑制浓度为50％。此外，苯并an吨酮衍生物5、6c，7a和7e表现出强力的拓扑异构酶I（Topo I）抑制作用，结果表明某些化合物具有发展为非喜树碱（CPT）拓扑异构酶I抑制剂的潜力。

  DOI：

  10.3109/14756366.2011.595712
• 作为产物：
  描述：

  间苯三酚 、 1-羟基-2-萘甲酸 以 三氯氧磷 为溶剂， 反应 6.0h， 以35.8%的产率得到6,8-dihydroxy-3,4-benzoxanthen-9-one
  参考文献：
  名称：

  合成新型苯并蒽酮类似物作为非喜树碱拓扑异构酶I抑制剂。

  摘要：

  铅化合物苯并an吨酮侧链的结构修饰提供了一系列苯并an吨酮类似物，其中首次报道了其中的12个。结果表明，这些化合物中的大多数对肿瘤细胞具有中等的细胞毒性，在微摩尔范围内的抑制浓度为50％。此外，苯并an吨酮衍生物5、6c，7a和7e表现出强力的拓扑异构酶I（Topo I）抑制作用，结果表明某些化合物具有发展为非喜树碱（CPT）拓扑异构酶I抑制剂的潜力。

  DOI：

  10.3109/14756366.2011.595712

文献信息

• NOVEL ANTICANCER-AIDING COMPOUND, METHOD FOR PREPARING THE SAME, ANTICANCER-AIDING COMPOSITION CONTAINING THE SAME AND METHOD FOR REDUCING ANTICANCER DRUG RESISTANCE USING THE SAME
  申请人：Na Young Hwa

  公开号：US20120190724A1

  公开（公告）日：2012-07-26

  The present invention provides a novel xanthone derivative compound or a pharmaceutically acceptable salt thereof. The compound is useful as a chemosensitizer that reduces anticancer drug resistance.

  本发明提供了一种新型黄酮衍生物化合物或其药用可接受盐。该化合物可用作化疗增敏剂，可降低抗癌药物的耐药性。
• Patel G N; Trivedi K N, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 4, p. 437 - 439
  作者：Patel G N、Trivedi K N

  DOI：——

  日期：——
• New benzoxanthone derivatives as topoisomerase inhibitors and DNA cross-linkers
  作者：Hee-Ju Cho、Mi-Ja Jung、Sangwook Woo、Jungsook Kim、Eung-Seok Lee、Youngjoo Kwon、Younghwa Na

  DOI：10.1016/j.bmc.2009.12.069

  日期：2010.2

  We synthesized 12 benzoxanthone derivatives classified as three different groups based on the tetracyclic ring shapes and evaluated their pharmacological activities to find potential anticancer agents. In the cytotoxicity test, most compounds showed effective cancer cell growth inhibition against the HT29 and DU145 cell lines. Among the compounds tested, compound 19 was the most effective in the cancer cell lines tested. Compound 9 showed dual inhibitory activities against DNA relaxation by topoisomerases I and II. The% inhibition of compound 9 on topoisomerase I was comparable to that of camptothecin. Compound 9 efficiently blocked topoisomerase II function by almost threefold than etoposide at 20 mu M. Compound 19 had selective topoisomerase II inhibitory activity at 100 mu M. The DNA cross-linking test revealed that only compounds 8 and 19, which possess epoxy groups, cross-linked DNA duplex, while 14 did not. From the combined pharmacological results, we proposed that the target through which compound 19 inhibits cancer cell growth may be the DNA duplex itself and/or DNA-topoisomerase II complex. (C) 2010 Elsevier Ltd. All rights reserved.
• US8846749B2
  申请人：——

  公开号：US8846749B2

  公开（公告）日：2014-09-30
• Xanthones with multiple roles against diabetes: their synthesis, structure‐activity relationship, and mechanism studies
  作者：Youhong Ke、Qinfang Xu、Jianling Hu、Jianrun Zhang、Shijian Chen、Zhijun Liu、Shuling Peng、Chao Zhang、Zhenqiang Chen、Heru Chen

  DOI：10.1002/ddr.22170

  日期：2024.4

  A four‐step synthetic process has been developed to prepare 1,3,5,8‐tetrahydroxyxanthone (2a) and its isomer 1,3,7,8‐tetrahydroxyxanthone (2b). 25 more xanthones were also synthesized by a modified scheme. Xanthone 2a was identified as the most active inhibitor against both α‐glucosidase and aldose reductase (ALR2), with IC₅₀ values of 7.8 ± 0.5 μM and 63.2 ± 0.6 nM, respectively, which was far active than acarbose (35.0 ± 0.1 μM), and a little more active than epalrestat (67.0 ± 3.0 nM). 2a was also confirmed as the most active antioxidant in vitro with EC₅₀ value of 8.9 ± 0.1 μM. Any structural modification including methylation, deletion, and position change of hydroxyl group in 2a will cause an activity loss in inhibitory and antioxidation. By applying a H₂O₂‐induced oxidative stress nematode model, it was confirmed that xanthone 2a can be absorbed by Caenorhabditis elegans and is bioavailable to attenuate in vivo oxidative stress, including the effects on lifespan, superoxide dismutase, Catalase, and malondialdehyde. 2a was verified with in vivo hypoglycemic effect and mitigation of embryo malformations in high glucose. All our data support that xanthone 2a behaves triple roles and is a potential agent to treat diabetic mellitus, gestational diabetes mellitus, and diabetic complications.