trans-dihydronarcistatin | 848631-01-6

• 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: trans-dihydronarcistatin
• 英文别名: (1R,13R,14S,18R,19S)-9,16,19-trihydroxy-16-oxo-5,7,15,17-tetraoxa-12-aza-16lambda5-phosphapentacyclo[11.7.0.02,10.04,8.014,18]icosa-2,4(8),9-trien-11-one；(1R,13R,14S,18R,19S)-9,16,19-trihydroxy-16-oxo-5,7,15,17-tetraoxa-12-aza-16λ5-phosphapentacyclo[11.7.0.02,10.04,8.014,18]icosa-2,4(8),9-trien-11-one
• CAS: 848631-01-6
• 化学式: C₁₄H₁₄NO₉P
• 分子量: 371.24
• InChiKey: PRXQHOXUYJMARM-HRQCSNBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  trans-dihydronarcistatin 在 Dowex 50WX₈-400 (sodium form) 作用下， 以 水 为溶剂， 以86 mg的产率得到3,4-cyclic phosphate sodium trans-dihydro-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
• 作为产物：
  描述：

  (2S,3R,4S,4aR,11bR)-2,3,4,7-tetrahydroxy-1,3,4,4a,5,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one 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 48.0h， 生成 trans-dihydronarcistatin
  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

• US7709643B2
  申请人：——

  公开号：US7709643B2

  公开（公告）日：2010-05-04
• Antineoplastic Agents. 527. Synthesis of 7-Deoxynarcistatin, 7-Deoxy-<i>trans</i>-dihydronarcistatin, and <i>trans</i>-Dihydronarcistatin 1
  作者：George R. Pettit、Noeleen Melody

  DOI：10.1021/np0304518

  日期：2005.2.1

  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.