8-香叶草氧基补骨脂素 | 7437-55-0

• 物质功能分类: 天然产物 - 香豆素
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 8-香叶草氧基补骨脂素
• 英文名称: 8-geranyloxypsoralen
• 英文别名: 8-geranoxypsoralen；8-GOP；9-(3,7-dimethyl-octa-2,6-dienyloxy)-furo[3,2-g]chromen-7-one；9-geranyloxy-furo[3,2-g]chromen-7-one；9-Geranyloxy-furo[3,2-g]chromen-7-on；Xanthotoxol geranyl ether；9-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one
• CAS: 7437-55-0
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: SOVNCTNQAWWYAQ-OQLLNIDSSA-N

物化性质

• 熔点：
  53-54 °C
• 沸点：
  503.7±50.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)
• 溶解度：
  溶于乙腈和氯仿
• LogP：
  5.850 (est)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S36,S37
• 危险类别码：
  R22,R43
• WGK Germany：
  3
• 储存条件：
  2-8°C

制备方法与用途

生物活性

8-去甲氧基异紫肖素（8-Geranyloxypsoralen）是从葡萄柚中分离出的一种呋喃香豆素，能有效抑制 P450 3A4 (CYP3A4)，其 IC50 值为 3.93 μM。

靶点

• IC50: 3.93 μM (P450 3A4)

反应信息

• 作为反应物：
  描述：

  8-香叶草氧基补骨脂素 在 disodium hydrogenphosphate 、 硫酸 、 双氧水 、 六氟丙酮 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 19.25h， 生成 花椒毒醇
  参考文献：
  名称：

  Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4

  摘要：

  Furanocoutnarins have been shown to inhibit CYP3A4 in vitro with varying degrees of potency [Pharmacogeneties 1997, 7, 391-396; Chem. Res. Toxicol. 1998, 11, 252-259; Drug Metab. Dispos. 1997, 25, 1228-1233; Br. J. Pharmacol 2000, 130, 13691377]. In this study, we report the effects of a series of novel furanocoumarins based on the naturally Occurring derivative 8-geranylepoxypsoralen which has been shown to be a more potent inhibitor of CYP3A4 than its 5-position-substituted counterpart bergamottin [Drug Metab. Dispos. 2000, 28, 766-771; Jpn. J. Pharmacol. 2000, 82, 122-129]. Compounds were designed, synthesised and tested for their ability to inhibit CYP3A4 activity in human liver microsomes using testosterone as the marker Substrate. Both the saturated and unsaturated phenolic furanocoumarin derivatives were found to be inactive. However, the 8-alkyloxy-furanocoumarin analogues were shown to inhibit CYP3A4 activity in a dose dependent manner, with IC50 values ranging from 0.78 +/- 0.11 to 3.93 +/- 0.53 mu M. The reduced furan derivative dihydro-8-geranyloxypsoralen showed a 4-fold decrease in inhibitory potency, suggesting that the furan moiety plays a role in the interaction between these compounds and CYP3A4. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.046
• 作为产物：
  描述：

  8-甲氧基补骨脂素 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 8-香叶草氧基补骨脂素
  参考文献：
  名称：

  天然香豆素作为β-分泌酶抑制剂的构效关系

  摘要：

  本研究证明可以评估天然香豆素（NOC）（包括简单香豆素，呋喃香豆素和吡喃香豆素）对β-分泌酶（BACE1）活性的抑制作用。在41个NOC中，一些呋喃香豆素抑制了BACE1的活性，但简单的香豆素和吡喃香豆素没有影响。最有效的抑制剂是5-香叶基氧基-8-甲氧基补骨脂素（31），IC 50值为9.9μM 。其他呋喃香豆素衍生物，例如8-香叶基氧基-5-甲氧基补骨脂素（35），8-香叶基氧基补骨脂蛋白（24）和佛手柑（18）抑制BACE1活性，IC 50值<25.0μM。通过狄克逊曲线和Cornish-鲍登地块抑制机制的分析表明，化合物18，31和35混合型抑制剂。香豆素24抑制BACE1的动力学是非竞争性抑制剂。

  DOI：

  10.1016/j.bmc.2011.12.002

文献信息

• Structures of Lansiumarin-A, -B, -C, Three New Furocoumarins from Clausena lansium.
  作者：Chihiro ITO、Shinya KATSUNO、Hiroshi FURUKAWA

  DOI：10.1248/cpb.46.341

  日期：——

  Three new furocoumarins named lansiumarin-A (1), -B (2), and -C (6) were isolated from the branches of Clausena lansium (Rutaceae), and their structures were elucidated by chemical and spectroscopic methods.

  从芸香科植物 Clausena lansium 的枝条中分离出三种新的呋喃香豆素，分别命名为 lansiumarin-A (1)、-B (2) 和 -C (6)，并通过化学和光谱方法阐明了它们的结构。
• FMO3 inhibitors for treating pain
  申请人：Akron Molecules GmbH

  公开号：EP2674161A1

  公开（公告）日：2013-12-18

  The present invention relates to new therapies to treat pain and related diseases, as well as pharmaceutical compounds for use in said therapies.

  本发明涉及治疗疼痛和相关疾病的新疗法，以及用于上述疗法的药物化合物。
• Pharmaceutical composition for treating or alleviating an autoimmune disease and/or complication thereof and/or nephritis and method for treating or alleviating an autoimmune disease and/or complication thereof and/or nephritis
  申请人：Industrial Technology Research Institute

  公开号：US10821148B2

  公开（公告）日：2020-11-03

  The present disclosure provides a pharmaceutical composition for treating or alleviating an autoimmune disease and/or complication thereof and/or nephritis, including: an effective amount of an extract of a plant belonging to Rutaceae as an effective ingredient for treating or alleviating the autoimmune disease and/or complication thereof and/or nephritis, wherein the autoimmune disease is selected from a group consisting of lupus erythematosus, psoriasis, psoriatic arthritis, ankylosing spondylitis, rheumatoid arthritis, juvenile idiopathic arthritis, Crohn's disease and ulcerative colitis (UC).

  本公开提供了一种用于治疗或缓解自身免疫性疾病和/或其并发症和/或肾炎的药物组合物，包括：有效量的芸香科植物提取物，作为治疗或缓解自身免疫性疾病和/或其并发症和/或肾炎的有效成分，其中自身免疫性疾病选自由红斑狼疮、银屑病、银屑病关节炎、强直性脊柱炎、类风湿性关节炎、幼年特发性关节炎、克罗恩病和溃疡性结肠炎（UC）组成的组。
• Natural oxyprenylated coumarins are modulators of melanogenesis
  作者：Serena Fiorito、Francesco Epifano、Francesca Preziuso、Ivana Cacciatore、Antonio di Stefano、Vito Alessandro Taddeo、Philippe de Medina、Salvatore Genovese

  DOI：10.1016/j.ejmech.2018.04.051

  日期：2018.5

  Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor 13 and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect. The parent compound with a free OH group, umbelliferone, did not provide any interaction. Other coumarins assayed, having shorter chains and/or being substituted in other positions, and prenyloxypsoralens, were not active or not further investigated in this context being cytotoxic at low doses. (C) 2018 Elsevier Masson SAS. All rights reserved.
• COMPOUNDS AND METHODS FOR TREATING PAIN
  申请人：Akron Molecules GmbH

  公开号：EP2637649A2

  公开（公告）日：2013-09-18