narcistatin | 496963-44-1

• 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: narcistatin
• 英文别名: nacistatin；(13R,14S,18R,19S)-9,19-dihydroxy-16-oxido-16-oxo-5,7,15,17-tetraoxa-12-aza-16lambda5-phosphapentacyclo[11.7.0.02,10.04,8.014,18]icosa-1(20),2,4(8),9-tetraen-11-one;hydron；(13R,14S,18R,19S)-9,19-dihydroxy-16-oxido-16-oxo-5,7,15,17-tetraoxa-12-aza-16λ5-phosphapentacyclo[11.7.0.02,10.04,8.014,18]icosa-1(20),2,4(8),9-tetraen-11-one;hydron
• CAS: 496963-44-1
• 化学式: C₁₄H₁₂NO₉P
• 分子量: 369.224
• InChiKey: YZQLZWYKYCWFGR-HPKWNKRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  narcistatin 在 calcium acetate 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以30 mg的产率得到calcium narcistatin
  参考文献：
  名称：

  Antineoplastic Agents 500. Narcistatin^,1

  摘要：

  An efficient procedure was found for synthetic conversion of the sparingly soluble anticancer isocarbostyril narciclasine (1), a component of various Narcissus species, to a cyclic phosphate designated narcistatin (3b). The reaction between narciclasine, tetrabutylammonium. dihydrogen phosphate, and p-toluenesulfonic acid in pyridine afforded pyridinium narcistatin (3a) in reasonable yields. Transformation of narcistatin (3a) to, for example, the water-soluble prodrug sodium narcistatin (3d) was easily achieved by cation exchange chromatography. Narcistatin (3b) and 15 salt derivatives were evaluated against a panel of human cancer cell lines, and the range (0.1-0.01) of GI(50) values in mug/mL was found to parallel that shown by the parent narciclasine.

  DOI：

  10.1021/np020225i
• 作为产物：
  描述：

  水仙环素 在 吡啶 、 四丁基磷酸氢铵 、 N,N'-二环己基碳二亚胺 作用下， 反应 96.0h， 生成 narcistatin
  参考文献：
  名称：

  Antineoplastic Agents. 527. Synthesis of 7-Deoxynarcistatin, 7-Deoxy-trans-dihydronarcistatin, and trans-Dihydronarcistatin 1

  摘要：

  The synthesis of sodium narcistatin (8) was improved (88% overall yield) and the modified reaction sequence was utilized to synthesize three new 3,4-cyclic phosphate prodrugs, sodium 7-deoxynarcistatin (5), sodium 7-deoxy-trans-dihydronarcistatin (6), and sodium trans-dihydronarcistatin (7). The human cancer cell line inhibitory isocarbostyril precursors were isolated from the bulbs of Hymenocallis littoralis obtained by horticultural production or reduction of narciclasine (1a --> 4) from the same source.

  DOI：

  10.1021/np0304518

文献信息

• Narcistatin prodrugs
  申请人：Pettit R. George

  公开号：US20060135481A1

  公开（公告）日：2006-06-22

  The present invention provides prodrugs derived from the sparingly soluble anticancer isocarbostyril narciclasine, a component of various Narcissus species, said prodrugs having potential for use against animal and human cancers. Also disclosed is an efficient procedure for the synthetic conversion of narciclasine to several more soluble cyclic phosphate compounds, including “narcistatin”.

  本发明提供了源自难溶性抗癌异喀巴斯亚胺的前药，该异喀巴斯亚胺是各种水仙属植物的成分，这些前药具有用于动物和人类癌症的潜力。本发明还公开了一种有效的程序，用于将异喀巴斯亚胺合成为几种更易溶的环磷酸酯化合物，包括“narcistatin”。
• NARCISTATIN PRODRUGS
  申请人：Pettit George R.

  公开号：US20090082569A1

  公开（公告）日：2009-03-26

  The present invention provides prodrugs derived from the sparingly soluble anticancer isocarbostyril narciclasine, a component of various Narcissus species, said prodrugs having potential for use against animal and human cancers. Also disclosed is an efficient procedure for the synthetic conversion of narciclasine to several more soluble cyclic phosphate compounds, including “narcistatin”.

  本发明提供从难溶性抗癌异喀巴斯蒂尔纳西克拉辛衍生的前药，纳西克拉辛是各种水仙属植物的成分，该前药具有用于治疗动物和人类癌症的潜力。还揭示了一种高效的合成转化纳西克拉辛为几种更易溶的环磷酸酯化合物的方法，包括“纳西斯塔丁”。
• SYNTHESIS OF SODIUM NARCISTATIN AND RELATED COMPOUNDS
  申请人：Pettit George R.

  公开号：US20090131672A1

  公开（公告）日：2009-05-21

  The present invention involves use of the compounds narciclasine (2a) and 7-deoxy-narciclasine (2c), which are obtained via isolation from the medicinal plant species Narcissus (Amaryllidaceae), as precursors in a novel synthesis method in which each of these compounds are selectively hydrogenated to produce trans-dihydronarciclasine (1a) and 7-deoxy-trans-dihydronarciclasine (1c). Also described herein is a novel synthesis method for producing sodium narcistatin (11) from narciclasine (2a). Further described herein are certain novel 3,4-cyclic phosphate prodrugs, including sodium-7-deoxynarcistatin (8), sodium-7-deoxy-transdihydronarcistatin (9), and sodium transdihydronarcistatin (10).

  本发明涉及使用从水仙属植物（石蒜科）中分离出的化合物纳西克拉辛（2a）和7-去氧纳西克拉辛（2c）作为前体物的新合成方法，其中每种化合物被选择性氢化以产生反式二氢纳西克拉辛（1a）和7-去氧-反式二氢纳西克拉辛（1c）。本文还描述了一种从纳西克拉辛（2a）中产生纳西斯他汀钠（11）的新合成方法。本文还描述了某些新型3,4-环磷酸酯前药，包括7-去氧纳西斯他汀钠（8）、7-去氧-反式二氢纳西斯他汀钠（9）和反式二氢纳西斯他汀钠（10）。
• Process for the preparation of narcistatin prodrugs
  申请人：ARIZONA BOARD OF REGENTS, A BODY CORPORATE OF THE STATE OF ARIZONA acting for and on behalf of ARIZONA STATE UNIVERSITY

  公开号：EP1990346A2

  公开（公告）日：2008-11-12

  The present invention provides prodrugs derived from the sparingly soluble anticancer isocarbostyril narciclasine, a component of various Narcissus species, said prodrugs having potential for use against human and animal cancers. Also disclosed is an efficient procedure for the synthetic conversion of narciclasine to several more soluble cyclic phosphate compounds, including "narcistatin".

  本发明提供了由稀溶性抗癌异卡波胆碱 narciclasine 衍生的原药，narciclasine 是多种水仙的一种成分，所述原药具有用于防治人类和动物癌症的潜力。此外，本发明还公开了一种将 narciclasine 合成为几种可溶性环磷酸化合物（包括 "narcistatin"）的有效方法。
• [EN] PHOSPHAMIDE DERIVATIVE, METHOD FOR MANUFACTURING THE SAME, AND USES THEREOF<br/>[FR] DÉRIVÉ DE PHOSPHAMIDE, SON PROCÉDÉ DE FABRICATION ET SES UTILISATIONS<br/>[ZH] 一种磷酰胺衍生物及制备方法和用途
  申请人：SICHUAN HAISCO PHARMACEUTICAL CO LTD

  公开号：WO2017133517A1

  公开（公告）日：2017-08-10

  公开了一种磷酰胺衍生物及制备方法和用途。特别公开了一种通式(I)所示化合物及其药学上可接受的盐或立体异构体 (I)，其中，G、L、Q、s如说明书中所定义。