4aβ,10bβ-Dihydro-narciclasin | 1194273-32-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 4aβ,10bβ-Dihydro-narciclasin
• 英文别名: Dihydro-narciclasin；Dihydro-lycoricidinol od. 1,2,3,8-Tetrahydroxy-6,7-methylendioxy-9-oxo-1,2,3,4,4a,9,10,10a-octahydro-10-aza-phenanthren；(4aR)-2t,3c,4c,7-tetrahydroxy-(4ar,11bξ)-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one；(2S,3R,4S,4aR)-2,3,4,7-tetrahydroxy-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
• CAS: 1194273-32-9
• 化学式: C₁₄H₁₅NO₇
• 分子量: 309.276
• InChiKey: SBTGHBALOCEVOR-NLGHJWSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4aβ,10bβ-Dihydro-narciclasin 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以129 mg的产率得到二氢水仙克拉辛碱
  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 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 4aβ,10bβ-Dihydro-narciclasin
  参考文献：
  名称：

  水仙子碱和水仙碱

  摘要：

  从许多种水仙花的新鲜鳞茎中提取了两种化合物。尽管它们的结构与许多金莲花科生物碱有关，但由于氮的特征是酰胺，因此这些化合物没有显示出碱性。第一种名为水仙子碱的物质显示出很强的抗有丝分裂活性，并被指定为结构VIII或其镜像。第二种化合物名为narciprimine，没有抗有丝分裂活性，并具有结构XII。

  DOI：

  10.1016/0040-4020(68)88061-5

文献信息

• Narciclasine and narciprimine
  作者：F. Piozzi、C. Fuganti、R. Mondelli、G. Ceriotti

  DOI：10.1016/0040-4020(68)88061-5

  日期：1968.1

  been extracted. Although their structures are related to many Amaryllidaceae alkaloids, the compounds show no basic properties since the nitrogen is amidic in character. The first substance, named narciclasine, shows a strong antimitotic activity and has been assigned structure VIII or its mirror image. The second compound, named narciprimine, has no antimitotic activity and has been given structure XII

  从许多种水仙花的新鲜鳞茎中提取了两种化合物。尽管它们的结构与许多金莲花科生物碱有关，但由于氮的特征是酰胺，因此这些化合物没有显示出碱性。第一种名为水仙子碱的物质显示出很强的抗有丝分裂活性，并被指定为结构VIII或其镜像。第二种化合物名为narciprimine，没有抗有丝分裂活性，并具有结构XII。
• Lycoricidinol and Lycoricidine, New Plant-growth Regulators in the Bulbs of Lycoris radiata HERB.
  作者：TOSHIHIKO OKAMOTO、YOSHIHIKO TORII、YO ISOGAI

  DOI：10.1248/cpb.16.1860

  日期：——
• Structure−Activity Relationship Analysis of Novel Derivatives of Narciclasine (an <i>Amaryllidaceae</i> Isocarbostyril Derivative) as Potential Anticancer Agents
  作者：Laurent Ingrassia、Florence Lefranc、Janique Dewelle、Laurent Pottier、Véronique Mathieu、Sabine Spiegl-Kreinecker、Sébastien Sauvage、Mohamed El Yazidi、Mischaël Dehoux、Walter Berger、Eric Van Quaquebeke、Robert Kiss

  DOI：10.1021/jm8013585

  日期：2009.2.26

  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.