1,3-dihydroxy-12H-benzo[b]xanthen-12-one | 22315-94-2

• 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: 1,3-dihydroxy-12H-benzo[b]xanthen-12-one
• 英文别名: 1,3-dihydroxy-12H-benzo[b]xanthone；1,3-dihydroxybenzoxanthone；1,3-dihydroxybenzo[b]xanthen-12-one
• CAS: 22315-94-2
• 化学式: C₁₇H₁₀O₄
• mdl: MFCD13969025
• 分子量: 278.264
• InChiKey: MSAPVEXKCXYFIM-UHFFFAOYSA-N

物化性质

• 熔点：
  283-285 °C
• 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：

  1,3-dihydroxy-12H-benzo[b]xanthen-12-one 在 硝酸 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以53%的产率得到1,3-Dihydroxy-4-nitrobenzo[b]xanthen-12-one
  参考文献：
  名称：

  Synthesis of xanthone derivatives with extended π-systems as α-glucosidase inhibitors: Insight into the probable binding mode

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.02.030
• 作为产物：
  描述：

  3-methoxy-2-naphthoyl chloride 在 吡啶 、 aluminum (III) chloride 、 四丁基氢氧化铵 、 氢溴酸 、 溶剂黄146 作用下， 以 乙醚 、 水 为溶剂， 反应 12.0h， 生成 1,3-dihydroxy-12H-benzo[b]xanthen-12-one
  参考文献：
  名称：

  含氮 酮衍生物及其制备方法和应用

  摘要：

  本发明公开了一种如式(I)和式(II)的含氮口山酮衍生物及其制备方法和应用，本发明合成了新的含氮口山酮衍生物并将其制成了盐酸盐，增加溶解性，同时活性研究表明部分化合物具有治疗和/或预防糖尿病及由糖尿病所引起的并发症的作用，可进一步进行开发研究作为新型治疗和/或预防糖尿病及由糖尿病所引起的并发症的药物。

  公开号：

  CN105294637B

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。
• Synthesis and biological evaluation of novel benzo[b]xanthone derivatives as potential antitumor agents
  作者：Lin Luo、Jiang-Ke Qin、Zhi-Kai Dai、Shi-Hua Gao

  DOI：10.2298/jsc120925060l

  日期：——

  Nine novel aminoalkoxy substituted benzo(b)xanthones (3a-i) were synthesized. Their antitumor activities were evaluated in five human solid tumor cell lines, including Hep-G2, BEL-7402, HeLa, MGC-803 and CNE, by the MTT (2-(4,5-dimethyl-thiazol-2-yl)-3,5-diphenyl-2H-tetrazolium bromide) method. The results showed that most of the compounds displayed moderate to good inhibitory activities on the tested

  合成了九种新颖的氨基烷氧基取代的苯并（b）氧杂蒽（3a-i）。通过MTT（2-（4,5-二甲基-噻唑-2-基）- 3，5-二苯基-2H-溴化四唑）法。结果表明，大多数化合物在体外对测试的癌细胞系表现出中等至良好的抑制活性，其中化合物3a和3h显示出比其他测试的化合物对大多数细胞系更高的抗肿瘤活性。探索了末端氨基和碳间隔基长度这两种结构因素对抗癌活性的影响，以探讨初步的结构-活性关系。
• Synthesis and Cytotoxic Activity of Benzopyranoxanthone Analogues of Benzo[b]acronycine and Psorospermine.
  作者：Chavalit SITTISOMBUT、Nadine COSTES、Sylvie MICHEL、Michel KOCH、François TILLEQUIN、Bruno PFEIFFER、Pierre RENARD、Alain PIERRÉ、Ghanem ATASSI

  DOI：10.1248/cpb.49.675

  日期：——

  3-hydroxy-2-naphthalenecarboxylic acid with phloroglucinol afforded 1,3-dihydroxy-12H-benzo[b]xanthen-12-one. Construction of an additional dimethylpyran ring onto this skeleton, by alkylation with 3-chloro-3-methyl-1-butyne followed by Claisen rearrangement, gave access to a series of benzo[b]pyrano[2,3-i]xanthen-6-ones and benzo[b]pyrano[3,2-h]xanthen-7-ones related to psorospermine and benzo[b]acronycine. In

  3-羟基-2-萘甲酸与间苯三酚缩合得到1，3-二羟基-12H-苯并[b]黄原-12-。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，从而可以得到一系列苯并[b]吡喃并[2,3-i]黄嘌呤-6 -Ponerospermine和benzo [b] acronycine相关的-ones和benzo [b] pyrano [3,2-h] xanthen-7-ones。与在吡啶并rid啶酮和苯并吡啶并ac啶酮系列中观察到的相反，线性苯并[b]-吡喃并[2,3-i]黄原-6-衍生物比它们的角苯并[b]吡喃并[3,2-]更有效。 h]黄嘌呤-7-异构体。顺式-3,4-二乙酰氧基-5-甲氧基-2,2-二甲基-3,4-二氢-2H，6H-苯并[b]吡喃并[2,3-i]黄嘌呤-6-中最活跃的新化合物，
• 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。
• Synthesis, inhibitory activities, and QSAR study of xanthone derivatives as α-glucosidase inhibitors
  作者：Yan Liu、Zhuofeng Ke、Jianfang Cui、Wen-Hua Chen、Lin Ma、Bo Wang

  DOI：10.1016/j.bmc.2008.06.043

  日期：2008.8

  Xanthones and their derivatives have been reported to exhibit strong inhibitory activities toward alpha-glucosidase. To provide deep insight into the correlation between inhibitory activities and structures of xanthones, multiple linear regression (MLR) method was employed to establish QSAR models for 43 xanthone derivatives that have diverse structures. Among the 38 typical descriptors investigated, Hs (number of H-bond forming substituents), N-pi (number of aromatic rings), and S (softness value) can be utilized to model the inhibitory activity. Thus, inhibitory activities of xanthone derivatives can be regulated by H-bond forming substituents, pi-stacking-forming aromatic rings and softness values on the xanthone skeleton. The accuracy and predictive power of the proposed QSAR model were verified by LOO validation, Y-randomization, and test group validation with newly synthesized xanthone derivatives. (C) 2008 Elsevier Ltd. All rights reserved.