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 | 133401-12-4

• 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
• 中文名称: 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
• 英文名称: Kuanoniamine C
• 英文别名: N-[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)ethyl]propanamide
• CAS: 133401-12-4
• 化学式: C₂₁H₁₈N₄OS
• 分子量: 374.466
• InChiKey: OHRPKUDJMIHDKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 氧气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以4%的产率得到N-[2-(7-Hydroxy-7H-6-thia-3,4,8-triaza-benzo[de]cyclopenta[b]anthracen-7-yl)-ethyl]-propionamide
  参考文献：
  名称：

  Sagitol, a pyridoacridine alkaloid from the sponge Oceanapia sagittaria

  摘要：

  The sponge Oceanapia sagittaria from Palau contained the known sponge metabolite dercitamide (1) and a new pyridoacridine alkaloid sagitol (2). The structure of sagitol (2) was determined by interpretation of spectral data and confirmed by oxidation of dercitamide (1). CD measurements suggest that sagitol (2) is not an artifact. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02163-6

文献信息

• 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.
• US9181251B2
  申请人：——

  公开号：US9181251B2

  公开（公告）日：2015-11-10
• Sagitol, a pyridoacridine alkaloid from the sponge Oceanapia sagittaria
  作者：Christine E. Salomon、D. John Faulkner

  DOI：10.1016/s0040-4039(96)02163-6

  日期：1996.12

  The sponge Oceanapia sagittaria from Palau contained the known sponge metabolite dercitamide (1) and a new pyridoacridine alkaloid sagitol (2). The structure of sagitol (2) was determined by interpretation of spectral data and confirmed by oxidation of dercitamide (1). CD measurements suggest that sagitol (2) is not an artifact. Copyright (C) 1996 Elsevier Science Ltd