9-butoxy-7H-furo[3,2-g]chromen-7-one | 15558-40-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 9-butoxy-7H-furo[3,2-g]chromen-7-one
• 英文别名: 8-butoxypsoralen；9-butoxy-7H-furo[3,2-g][1]benzopyran-7-one；8-buthoxypsoralen；9-butoxy-furo[3,2-g]chromen-7-one；9-Butoxy-furo[3,2-g]chromen-7-on；9-butoxyfuro[3,2-g]chromen-7-one
• CAS: 15558-40-4
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: PZWODXOXODBAIP-UHFFFAOYSA-N

物化性质

• 熔点：
  87 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  436.3±45.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-甲氧基补骨脂素 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 48.0h， 生成 9-butoxy-7H-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  欧前胡素类似物的合成及其作为乙酰胆碱酯酶和丁酰胆碱酯酶抑制剂的评价

  摘要：

  在这项研究中，我们使用欧前胡素和黄花素作为底物合成了几种欧前胡素类似物。根据改良的 Ellman 方法在体外实验中评估所有化合物的抗胆碱酯酶活性。对于每种合成的化合物，确定了两种酶的 IC50 值。加兰他敏氢溴酸盐用作酶促实验中的阳性对照。所有活性化合物均显示出对丁酰胆碱酯酶 (BuChE) 而非乙酰胆碱酯酶的选择性。最活跃的是 8-(3-甲基丁氧基)-补骨脂素和 8-己氧基补骨脂素，BuChE 的 IC50 值分别约为 16.5 和 16.4 µM。我们的研究结果可能被视为基于天然呋喃香豆素结构寻找潜在抗阿尔茨海默病药物的开始。

  DOI：

  10.1002/ardp.201300259

文献信息

• Experiments with Xanthotoxin and Imperatorin Obtained from the Fruits of Ammi majus (L.)
  作者：Alexander Schönberg、Aly Sina

  DOI：10.1021/ja01166a523

  日期：1950.10
• Noncovalent attachment of psoralen derivatives with DNA: Hartree–Fock and density functional studies on the probes
  作者：Tarek M El-Gogary、Eman M El-Gendy

  DOI：10.1016/s1386-1425(03)00038-6

  日期：2003.9

  Two psoralen derivatives (probes) were prepared. Their geometries were optimized at the Hartree-Fock (HF) and Density Functional (B3LYP) levels employing 6-31G** and cc-pVDZ basis sets. Their interaction with DNA was investigated using spectrophotometric and computational techniques. Both of them have shown strong binding to calf thymus DNA. The red-shift and hypochromism that detected in the spectrum were taken as an evidence for the strong interaction between these probes and DNA. The spectrophotometric DNA titration data were treated by two different methodologies to calculate the intercalation affinity. Half-reciprocal plots gave binding constants of 5.5065 x 10(4) and 6. 4727 x 10(4) for 8-butoxypsoralen (8-BOP) and 8-hexoxypsoralen (8-HOP), respectively. Schatchard plots gave a comparable intercalation binding constants and also the surface binding constants along with the number of intercalated probe molecules per base pair. The interaction between these probes and DNA were studied theoretically. The energy of interaction was computed using molecular mechanics method. Strength of interaction of these probes with different types of DNA was computed and compared. Calculated energies of interaction were compared with the observed intercalation affinities. HOMO and LUMO energies were computed and used to account for the strength of interaction. (C) 2003 Elsevier B.V. All rights reserved.
• Deng, Xian-Qing; Wei, Cheng-Xi; Song, Ming-Xia, Arzneimittel-Forschung/Drug Research, 2010, vol. 60, # 10, p. 587 - 592
  作者：Deng, Xian-Qing、Wei, Cheng-Xi、Song, Ming-Xia、Quan, Zhe-Shan

  DOI：——

  日期：——
• METHODS AND SYSTEMS FOR TREATING CELL PROLIFERATION DISORDERS WITH PSORALEN DERIVATIVES
  申请人：IMMUNOLIGHT, LLC

  公开号：US20170113061A1

  公开（公告）日：2017-04-27

  Psoralen compounds of compounds having formulae 1A-10A, 1B-10B, 1C-10C, 1D-10D, 1E-10E, 1F-10F, 1G-10G, and 1H-5H as shown in FIG. 1, and pharmaceutically acceptable salts thereof; and their use in methods for the treatment of a cell proliferation disorder in a subject, pharmaceutical compositions containing the psoralen derivatives, a kit for performing the method, and a method for causing an auto vaccine effect in a subject using the method.
• Synthesis of Imperatorin Analogs and Their Evaluation as Acetylcholinesterase and Butyrylcholinesterase Inhibitors
  作者：Sebastian Granica、Anna K. Kiss、Małgorzata Jarończyk、Jan K. Maurin、Aleksander P. Mazurek、Zbigniew Czarnocki

  DOI：10.1002/ardp.201300259

  日期：2013.11

  In this study, we synthesized several imperatorin analogs using imperatorin and xanthotoxin as substrates. The anti‐cholinesterase activities of all compounds were evaluated in in vitro experiments according to the modified Ellman's method. For each synthesized compound, IC50 values for both enzymes were established. Galantamine hydrobromide was used as a positive control in the enzymatic experiments

  在这项研究中，我们使用欧前胡素和黄花素作为底物合成了几种欧前胡素类似物。根据改良的 Ellman 方法在体外实验中评估所有化合物的抗胆碱酯酶活性。对于每种合成的化合物，确定了两种酶的 IC50 值。加兰他敏氢溴酸盐用作酶促实验中的阳性对照。所有活性化合物均显示出对丁酰胆碱酯酶 (BuChE) 而非乙酰胆碱酯酶的选择性。最活跃的是 8-(3-甲基丁氧基)-补骨脂素和 8-己氧基补骨脂素，BuChE 的 IC50 值分别约为 16.5 和 16.4 µM。我们的研究结果可能被视为基于天然呋喃香豆素结构寻找潜在抗阿尔茨海默病药物的开始。