19-N-methoxyaminocolchicine | 916460-26-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 19-N-methoxyaminocolchicine
• 英文别名: 2-(methoxyamino)-N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• CAS: 916460-26-9
• 化学式: C₂₃H₂₈N₂O₇
• 分子量: 444.485
• InChiKey: QGRDJLRFCLIDEC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  19-N-methoxyaminocolchicine 、 D-glucurono-6,3-lactone 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-[[(3R,3aR,6S,6aR)-3,6-dihydroxy-5-oxo-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-2-yl]-methoxyamino]-N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
  参考文献：
  名称：

  Colchicine Glycorandomization Influences Cytotoxicity and Mechanism of Action

  摘要：

  The reaction of 70 unprotected, diversely functionalized free reducing sugars with methoxyamine-appended colchicine led to the production of a 58-member glycorandomized library. High-throughput cytotoxicity assays revealed glycosylation to modulate specificity and potency. Library members were also identified which, unlike the parent natural product (a destabilizer), stabilized in vitro tubulin polymerization in a manner similar to taxol. This study highlights a simple extension of neoglycorandomization toward amine-bearing scaffolds and the potential benefit of glycosylating nonglycosylated natural products.

  DOI：

  10.1021/ja064686s
• 作为产物：
  描述：

  19-[N-(tert-butoxycarbonyl)-N-methoxy]aminocolchicine 在 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以73%的产率得到19-N-methoxyaminocolchicine
  参考文献：
  名称：

  [EN] COLCHICINE NEOGLYCOSIDES AND METHODS FOR THEIR SYNTHESIS AND USE
  [FR] NÉOGLYCOSIDES DE COLCHICINE ET PROCÉDÉS POUR LEUR SYNTHÈSE ET UTILISATION

  摘要：

  公开号：

  WO2008067039A3

文献信息

• COLCHICINE NEOGLYCOSIDES AND METHODS FOR THEIR SYNTHESIS AND USE
  申请人：Thorson Jon S.

  公开号：US20080171787A1

  公开（公告）日：2008-07-17

  Colchicine neoglycosides, method for their synthesis and methods for their use are disclosed. The invention provides analogs of colchicine glycosylated to include a sugar moiety on a colchicine scaffold that is generally unglycosylated in nature. The colchicine neoglycosides disclosed herein are shown to have cytotoxic effects equivalent to at least the known cytotoxins paclitaxel and doxorubicin. Further, the neoglycosides disclosed according to the invention have physiologic effects not previously recognized in the alkaloid family that includes colchicine but recognized in other cytotoxic drug families such as the taxanes which act by stabilizing tubulin formation.
• US8232254B2
  申请人：——

  公开号：US8232254B2

  公开（公告）日：2012-07-31
• Colchicine Glycorandomization Influences Cytotoxicity and Mechanism of Action
  作者：Aqeel Ahmed、Noël R. Peters、Megan K. Fitzgerald、James A. Watson,、F. Michael Hoffmann、Jon S. Thorson

  DOI：10.1021/ja064686s

  日期：2006.11.1

  The reaction of 70 unprotected, diversely functionalized free reducing sugars with methoxyamine-appended colchicine led to the production of a 58-member glycorandomized library. High-throughput cytotoxicity assays revealed glycosylation to modulate specificity and potency. Library members were also identified which, unlike the parent natural product (a destabilizer), stabilized in vitro tubulin polymerization in a manner similar to taxol. This study highlights a simple extension of neoglycorandomization toward amine-bearing scaffolds and the potential benefit of glycosylating nonglycosylated natural products.
• [EN] COLCHICINE NEOGLYCOSIDES AND METHODS FOR THEIR SYNTHESIS AND USE<br/>[FR] NÉOGLYCOSIDES DE COLCHICINE ET PROCÉDÉS POUR LEUR SYNTHÈSE ET UTILISATION
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2008067039A3

  公开（公告）日：2008-08-14