(-)-3-O-acetylspectaline | 709046-67-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (-)-3-O-acetylspectaline
• 英文别名: (2R,3R,6S)-2-methyl-6-(13-oxotetradecyl)piperidin-3-yl acetate；[(2R,3R,6S)-2-methyl-6-(13-oxotetradecyl)piperidin-3-yl] acetate
• CAS: 709046-67-3
• 化学式: C₂₂H₄₁NO₃
• 分子量: 367.572
• InChiKey: LRKWDKCSHJWJST-BAGYTPMASA-N

物化性质

• 熔点：
  36.7-39.7 °C
• 沸点：
  459.7±30.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-3-O-acetylspectaline 在 甲醇 、 magnesium 作用下， 反应 56.0h， 以28.3 mg的产率得到(-)-spectaline
  参考文献：
  名称：

  Further Bioactive Piperidine Alkaloids from the Flowers and Green Fruits of Cassia spectabilis

  摘要：

  The flowers of Cassia spectabilis yielded three new piperidine alkaloids, (-)-3-O-acetylspectaline (1), (-)-7-hydroxyspectaline (2), and iso-6-spectaline (3), together with the known (-)-spectaline (4). The green fruits of this plant were also investigated, resulting in the isolation of 1 and 4. Their structures were elucidated using a combination of multidimensional NMR and MS techniques, and relative stereochemistries were established by NOESY correlations and analysis of coupling constants. The DNA-damaging activity of these compounds was evaluated using a mutant yeast, Saccharomyces cerevisiae, assay.

  DOI：

  10.1021/np0303963
• 作为产物：
  描述：

  乙酰氯 、 (-)-spectaline 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 3.5h， 以94%的产率得到(-)-3-O-acetylspectaline
  参考文献：
  名称：

  质谱用于鉴定同源哌啶生物碱及其作为乙酰胆碱酯酶抑制剂的活性。

  摘要：

  原理番泻叶中的哌啶生物碱是一种罕见的天然产物，具有多种生物活性。然而，不存在发色团使得通过常规方法阐明其结构成为巨大的挑战。在这种情况下，质谱分析法已成为代谢组学研究的强大工具。方法采用电喷雾电离串联质谱法（ESI-MS）研究哌啶生物碱（-）-酪氨酸和（-）-甲壳素以及半合成衍生物（-）-3-O-乙酰甲壳素和（-）-3-O-乙酰甲壳素/ MS）的正离子模式和电子电离质谱（EI-MS）。ESI碎片研究使用四极杆飞行时间仪器进行；使用氮气作为碰撞气体。通过生物自显影术和微孔板筛选测定法评估所研究化合物的乙酰胆碱酯酶抑制活性。结果ESI-MS / MS和EI-MS提供了有关哌啶化合物结构的有价值的补充信息。碰撞诱导的离解实验（MS / MS）表明，水或乙酸的中性消除是主要的裂解途径，这与（-）-酪氨酸和（-）-壮观碱以及半合成衍生物（-）提出的立体化学相符-3-O-乙酰基酪氨酸和（-）-3-O-乙酰基酞菁。结论ESI-MS

  DOI：

  10.1002/rcm.8172

文献信息

• Isolation, leishmanicidal evaluation and molecular docking simulations of piperidine alkaloids from Senna spectabilis
  作者：Rosimeire Borges Moreira Lacerda、Thamires Rodrigues Freitas、Mário Machado Martins、Thaise Lara Teixeira、Cláudio Vieira da Silva、Pamela Aparecida Candido、Ronaldo Junio de Oliveira、Claudio Viegas Júnior、Vanderlan da Silva Bolzani、Amanda Danuello、Marcos Pivatto

  DOI：10.1016/j.bmc.2018.10.032

  日期：2018.12

  Asia, and the Americas. Many natural products, particularly alkaloids, have been reported to have inhibitory activity against arginase, the key enzyme in the pathology caused by Leishmania sp. In this way, piperidine alkaloids (–)-cassine (1), (–)-spectaline (2), (–)-3-O-acetylcassine (3), and (–)-3-O-acetylspectaline (4) were isolated from Senna spectabilis flowers. These compounds (1/2 and 3/4) initially

  利什曼病是最重要的被忽视的热带病之一，在非洲，亚洲和美洲等发展中国家的低收入人群中尤其常见。据报道，许多天然产物，特别是生物碱，对精氨酸酶具有抑制活性，精氨酸酶是利什曼原虫引起的病理学中的关键酶。这样，哌啶生物碱（–）-酪氨酸（1），（–）-壮观碱（2），（–）-3- O-乙酰酪氨酸（3）和（–）-3- O-乙酰光谱（4）从番泻叶花中分离出来。这些化合物（1 / 2和3/ 4）最初以同源混合物的形式通过高效液相色谱进行分离，并针对亚马逊利什曼原虫的前鞭毛体相进行了评价。此外，分子对接模拟，以探测配体的结合方式实施了1 - 4到的活性位点的氨基酸亚马逊利什曼原虫精氨酸酶。生物碱2（IC 50 15.81μgmL -1）对亚马逊乳酸杆菌最有效。具有较大侧链的化合物2和4比化合物1对寄生虫更有效和3。对Vero细胞的细胞活力测试表明，化合物2（CC 50 66.67μgmL -1）最具毒性。母体结构的3-
• Antimalarial Activity of Piperidine Alkaloids from<i>Senna spectabilis</i>and Semisynthetic Derivatives
  作者：Marcos Pivatto、Luciene R. Baccini、Abhinay Sharma、Myna Nakabashi、Amanda Danuello、Claudio Viegas Júnior、Celia R. S. Garcia、Vanderlan S. Bolzani

  DOI：10.5935/0103-5053.20140195

  日期：——

  In our continuing work looking for new anti-infective lead compounds from Brazilian biomes, the two known piperidine alkaloids (-)-cassine and (-)-spectaline were isolated from the flowers of Senna spectabilis (syn. Cassia spectabilis). Their structures were elucidated using a combination of spectroscopic and spectrometric data analysis. Further, these compounds were acetylated yielding the derivatives (-)-3-O-acetylcassine and (-)-3-O-acetylspectaline. All compounds were screened against P. falciparum-infected red blood cells (RBC) in culture, aiming to identify antimalarial prototypes. Among all compounds screened, the first two alkaloids (IC50 1.82 mu M and IC50 2.76 mu M) were more effective than the derivatives (IC50 24.47 mu M and IC50 25.14 mu M) in comparison to the standard compound chloroquine (IC50 0.30 mu M). These data show that piperidine alkaloids constitute a class of natural products that feature a broad spectrum of biological activities, and are, therefore, important templates for drug design, including antimalarial.
• New selective acetylcholinesterase inhibitors designed from natural piperidine alkaloids
  作者：Cláudio Viegas、Vanderlan S. Bolzani、Luísa S.B. Pimentel、Newton G. Castro、Rafael F. Cabral、Rodrigo S. Costa、Corinne Floyd、Mônica S. Rocha、Maria C.M. Young、Eliezer J. Barreiro、Carlos A.M. Fraga

  DOI：10.1016/j.bmc.2005.04.030

  日期：2005.7

  Five new piperidine alkaloids were designed from natural (-)-3-O-acetyl-spectaline and (-)-spectaline that were obtained from the flowers of Senna spectabilis (sin. Cassia spectabilis, Leguminosae). Two semi-synthetic analogues (7 and 9) inhibited rat brain acetylcholinesterase, showing IC50 of 7.32 and 15.1 mu M, and were 21 and 9.5 times less potent against rat brain butyrylcholinesterase, respectively. Compound 9 (1 mg/kg, ip) was fully efficacious in reverting scopolamine-induced amnesia in mice. The two active compounds (7 and 9) did not show overt toxic effects at the doses tested in vivo. (c) 2005 Elsevier Ltd. All rights reserved.