9,11-dihydroxy-12H-benzo[a]xanthen-12-one | 53865-04-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 9,11-dihydroxy-12H-benzo[a]xanthen-12-one
• 英文别名: 6,8-dihydroxy-1,2-benzoxanthen-9-one；9,11-dihydroxy-benzo[a]xanthen-12-one；1,3-Dihydroxy-7,8-benzoxanthon；9,11-dihydroxybenzo[a]xanthen-12-one
• CAS: 53865-04-6
• 化学式: C₁₇H₁₀O₄
• mdl: MFCD13969028
• 分子量: 278.264
• InChiKey: DPSVULZFFRWBMZ-UHFFFAOYSA-N

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：

  9,11-dihydroxy-12H-benzo[a]xanthen-12-one 在 四氧化锇 、 水 、 sodium hydride 、 potassium carbonate 、 N-甲基吗啉氧化物 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 77.0h， 生成 (+/-)-cis-1,2-dihydroxy-6-methoxy-3,3-dimethyl-1,2-dihydro-3H,7H-benzo[a]pyrano[3,2-h]xanthen-7-one
  参考文献：
  名称：

  苯过培胺，丙烯醛和苯并[a]阿卡洛霉素的苯并[a]吡喃并[3,2-h]和[2,3-i] x吨酮类似物的合成和细胞毒活性。

  摘要：

  将2-羟基-1-萘甲酸与间苯三酚缩合，得到9,11-二羟基-12H-苯并[a]黄原-12-（6）。通过用3-氯-3-甲基-1-丁炔进行烷基化，然后进行克莱森重排，在该骨架上构建一个额外的二甲基吡喃环，可以得到6-羟基-3,3-二甲基-3H，7H-苯并[a]吡喃并[3,2-h]黄嘌呤-7-一（12）和5-羟基-2,2-二甲基-2H，6H-苯并[a]吡喃并[2,3-i]黄嘌呤-6-（13 ），将其甲基化为6-甲氧基-3,3-二甲基-3H，7H-苯并[a]吡喃并[3,2-h]黄嘌呤-7-一（14）和5-甲氧基-2,2-二甲基-2H，6H-苯并[a]吡喃并[2，3-i]黄嘌呤-6-一（15）。四氧化14和15的氧化得到相应的（+/-）-顺式二醇16和17，其在酰化后得到相应的酯18-21。同样，2-羟基-1-萘甲酸与3的缩合，5-二甲氧基苯胺得到11-氨基-9-甲氧基-12H-苯并[a]黄原-12

  DOI：

  10.1248/cpb.54.1113
• 作为产物：
  描述：

  2,4,6-三羟基苯甲酸 、 2-萘酚 在 zinc(II) chloride 、 三氯氧磷 作用下， 反应 5.0h， 以7.2%的产率得到9,11-dihydroxy-12H-benzo[a]xanthen-12-one
  参考文献：
  名称：

  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

  摘要：

  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。

  公开号：

  US20120190724A1

文献信息

• 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：US08846749B2

  公开（公告）日：2014-09-30

  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学上可接受的盐。该化合物可用作化疗增敏剂，可减少抗癌药物的耐药性。
• 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.
• Synthesis of xanthone derivatives with extended π-systems as α-glucosidase inhibitors: Insight into the probable binding mode
  作者：Yan Liu、Lin Ma、Wen-Hua Chen、Bo Wang、Zun-Le Xu

  DOI：10.1016/j.bmc.2007.02.030

  日期：2007.4

  A series of novel xanthone derivatives with extended pi-systems, that is, benzoxanthones 2-4, and their structurally perturbed analogs 5-9 have been designed and synthesized as alpha-glucosidase inhibitors. Their inhibitory activities toward yeast's alpha-glucosidase were evaluated with the aim to enrich the structure-activity relationship. The results indicated that benzoxanthones 2-4 were capable of inhibiting in vitro yeast's alpha-glucosidase 17- to 28-fold more strongly than xanthone derivative I that has smaller conjugated pi-system. Benzoxanthone 8, bearing angularly fused aromatic rings, and reduced benzoxanthone 5 showed decreased activities, strongly suggesting that linearly conjugated pi-systems play a crucial role in the inhibition process. O-Methylation of 3-OH of benzoxanthone 2 and nitration at C4 position led to a large decrease in the activity. This indicates that 3-OH of benzoxanthone was crucial to the inhibitory activity, primarily as an H-bonding donor. The present results suggest that pi-pi stacking effect and H-bonding make substantial contributions to elicit the inhibitory activities of this general class of inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.
• US8846749B2
  申请人：——

  公开号：US8846749B2

  公开（公告）日：2014-09-30