3-(3-Bromopropoxy)-1-hydroxybenzo[b]xanthen-12-one | 1068126-43-1

• 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: 3-(3-Bromopropoxy)-1-hydroxybenzo[b]xanthen-12-one
• CAS: 1068126-43-1
• 化学式: C₂₀H₁₅BrO₄
• 分子量: 399.241
• InChiKey: VAWCTEGYUJHLRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-Bromopropoxy)-1-hydroxybenzo[b]xanthen-12-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以28%的产率得到11-Hydroxy-2,8-dioxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3(12),4(9),10,14,16,18,20-octaen-13-one
  参考文献：
  名称：

  Synthesis, inhibitory activities, and QSAR study of xanthone derivatives as α-glucosidase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.06.043
• 作为产物：
  描述：

  间苯三酚 在 potassium carbonate 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 3-(3-Bromopropoxy)-1-hydroxybenzo[b]xanthen-12-one
  参考文献：
  名称：

  新型苯并[b] x吨酮衍生物作为潜在抗肿瘤药的合成及生物学评价

  摘要：

  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。

  DOI：

  10.2298/jsc120925060l

文献信息

• 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.
• 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。