N-Deacetylkuanoniamine D

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-Deacetylkuanoniamine D
• 英文别名: 2-(4-thia-6,9,19-triazapentacyclo[10.7.1.03,7.08,20.013,18]icosa-1,3(7),5,8,10,12(20),13,15,17-nonaen-2-yl)ethanamine
• 化学式: C₁₈H₁₄N₄S
• 分子量: 318.402
• InChiKey: XQGLKIJVEQNZIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  92.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-[2-(8H-吡啶并[4,3,2-mn][1,3]噻唑并[4,5-b]吖啶-9-基)乙基]丙酰胺 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以49 mg的产率得到N-Deacetylkuanoniamine D
  参考文献：
  名称：

  Bioactive Pyridoacridine Alkaloids from the Micronesian Sponge Oceanapia sp.

  摘要：

  The Micronesian sponge Oceanapia sp. afforded three pyridoacridine alkaloids: the known compounds kuanoniamine C (1) and kuanoniamine D (2), as well as the new N-deacyl derivative (3) of the kuanoniamines. Compounds 1 and 2 exhibited insecticidal activity toward neonate larvae of the polyphagous pest insect Spodoptera littoralis (LC50 of 156 and 59 ppm, respectively), when incorporated into artificial diet. Both compounds also showed toxicity in the brine shrimp lethality test with a LC50 of 37 mu g/mL (compound 1) and 19 mu g/mL (compound 2), respectively. The N-deacyl derivative did not show any remarkable effect in both bioassays. Cytotoxicity of the alkaloids was studied in vitro, using two human cell lines. The new derivative (3) appeared to be active in the same range of concentrations as kuanoniamine C (1) and D (2). The IC50 of 3 was 1.2 mu g/mL toward HeLa cells and 2.0 mu g/mL toward MONO-MAC 6 cells. In receptor binding assays compound 2 showed affinity to A(1)- and A(2A)-adenosine receptors with K-i values of 2.94 and 13.7 mu M, respectively. Compound 1 was less active than compound 2, whereas compound 3 showed no affinity toward adenosine receptors. In addition, compounds 1-3 exhibited moderate affinity to benzodiazepine binding sites of GABA(A) receptors.

  DOI：

  10.1021/np9702704

文献信息

• Extracts of Curcuma and Methods of Use Thereof
  申请人：Alberte Randall S.

  公开号：US20100098788A1

  公开（公告）日：2010-04-22

  The present invention relates in part to turmeric extracts that are useful for treating or preventing neurodegenerative disorders. Another aspect of the invention relates in part to turmeric extracts that are useful for treating or preventing inflammatory disorders. In some embodiments, the extracts comprise at least one compound selected from the group consisting of 25 to 500 μg bamosamine, 25 to 750 μg echinaxanthol, 100 to 3,000 μg bisdemethoxycurcumin, 50 to 500 μg daphniyunnine E and 500 to 75,000 μg curcumin per 100 mg of extract. Another aspect of the invention relates to pharmaceutical compositions comprising the aforementioned extracts. Another aspect of the invention relates to methods of treating or preventing neurodegenerative disorders comprising administering to a subject in need thereof an effective amount of the aforementioned extracts or compositions. Another aspect of the invention relates to methods of making the aforementioned extracts.
• Bioactive Pyridoacridine Alkaloids from the Micronesian Sponge <i>Oceanapia </i>sp.
  作者：Claudia Eder、Peter Schupp、Peter Proksch、Victor Wray、Klaus Steube、Christa E. Müller、Wolfram Frobenius、Markus Herderich、Rob W. M. van Soest

  DOI：10.1021/np9702704

  日期：1998.2.1

  The Micronesian sponge Oceanapia sp. afforded three pyridoacridine alkaloids: the known compounds kuanoniamine C (1) and kuanoniamine D (2), as well as the new N-deacyl derivative (3) of the kuanoniamines. Compounds 1 and 2 exhibited insecticidal activity toward neonate larvae of the polyphagous pest insect Spodoptera littoralis (LC50 of 156 and 59 ppm, respectively), when incorporated into artificial diet. Both compounds also showed toxicity in the brine shrimp lethality test with a LC50 of 37 mu g/mL (compound 1) and 19 mu g/mL (compound 2), respectively. The N-deacyl derivative did not show any remarkable effect in both bioassays. Cytotoxicity of the alkaloids was studied in vitro, using two human cell lines. The new derivative (3) appeared to be active in the same range of concentrations as kuanoniamine C (1) and D (2). The IC50 of 3 was 1.2 mu g/mL toward HeLa cells and 2.0 mu g/mL toward MONO-MAC 6 cells. In receptor binding assays compound 2 showed affinity to A(1)- and A(2A)-adenosine receptors with K-i values of 2.94 and 13.7 mu M, respectively. Compound 1 was less active than compound 2, whereas compound 3 showed no affinity toward adenosine receptors. In addition, compounds 1-3 exhibited moderate affinity to benzodiazepine binding sites of GABA(A) receptors.