cis-1,10b-Dihydro-narciclasin-acetonid | 55659-25-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cis-1,10b-Dihydro-narciclasin-acetonid
• 英文别名: 6,12-dihydroxy-2,2-dimethyl-3b,4,10b,11,12,12a-hexahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one；(3aS)-6,12c-dihydroxy-2,2-dimethyl-(3ar,3bt,10bt,12ac)-3b,4,10b,11,12,12a-hexahydro-3aH-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridin-5-one；(1S,13R,14S,18R,19S)-9,19-dihydroxy-16,16-dimethyl-5,7,15,17-tetraoxa-12-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-2,4(8),9-trien-11-one
• CAS: 55659-25-1
• 化学式: C₁₇H₁₉NO₇
• 分子量: 349.34
• InChiKey: PWWBPUNUKQOTSZ-XAZSNKFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  cis-1,10b-Dihydro-narciclasin-acetonid 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以77%的产率得到(3aS,3bR,10bS,12aS)-6-hydroxy-2,2-dimethyl-3a,3b,4,10b,11,12a-hexahydrobis([1,3]dioxolo)[4,5-c:4',5'-j]phenanthridine-5,12-dione
  参考文献：
  名称：

  Structure−Activity Relationship Analysis of Novel Derivatives of Narciclasine (an Amaryllidaceae Isocarbostyril Derivative) as Potential Anticancer Agents

  摘要：

  Narciclasine (1) is a plant growth regulator that has been previously demonstrated to be proapoptotic to cancer cells at high concentrations (>= 1 mu M). Data generated in the present study show that narciclasine displays potent antitumor effects in apoptosis-resistant as well as in apoptosis-sensitive cancer cells by impairing the organization of the actin cytoskeleton in cancer cells at concentrations that are not cytotoxic (IC50 values of 30-90 nM). The current study further revealed that any chemical modification to the narciclasine backbone generally led to compounds of variable stability, weaker activity, or even the complete loss of antiproliferative effects in vitro. However, one hemisynthetic derivative of narciclasine, compound 7k, demonstrated by both the intravenous and oral routes higher in vivo antitumor activity in human orthotopic 4, glioma models in mice when compared to narciclasine at nontoxic doses. Narciclasine and compound 7k may therefore be of potential use to combat brain tumors.

  DOI：

  10.1021/jm8013585
• 作为产物：
  描述：

  水仙环素 在 barium dihydroxide 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 乙醇 为溶剂， 生成 cis-1,10b-Dihydro-narciclasin-acetonid
  参考文献：
  名称：

  Mondon,A.; Krohn,K., Chemische Berichte, 1975, vol. 108, p. 445 - 463

  摘要：

  DOI：