(-)-O-<(2,2,5,5-tetramethyl-1-oxy-3-pyrrolidinyl)carbonyl>-4-(hydroxymethyl)colchicine | 92220-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (-)-O-<(2,2,5,5-tetramethyl-1-oxy-3-pyrrolidinyl)carbonyl>-4-(hydroxymethyl)colchicine
• 英文别名: (-)-O-[(2,2,5,5-tetramethyl-1-oxy-3-pyrrolidinyl)carbonyl]-4-(hydroxymethyl)colchicine
• CAS: 92220-81-0
• 化学式: C₃₂H₄₁N₂O₉
• 分子量: 597.686
• InChiKey: NMGZVFZILBSACF-WCSIJFPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N-[(7S)-4-(羟基甲基)-1,2,3,10-四甲氧基-9-氧代-6,7-二氢-5H-苯并[d]庚搭烯-7-基]乙酰胺 、 3-羧基-PROXYL 在 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以34%的产率得到(-)-O-<(2,2,5,5-tetramethyl-1-oxy-3-pyrrolidinyl)carbonyl>-4-(hydroxymethyl)colchicine
  参考文献：
  名称：

  Synthesis and binding to tubulin of colchicine spin probes

  摘要：

  Spin probes of deacetylcholchicine (1), 4-(hydroxymethyl)colchicine (2), and colchifoline (3) have been synthesized to study the binding site for colchicine on tubulin. Acylation of 1-3 with (+/-)-2,2,5,5-tetramethyl-1-pyrrolidinyloxy-3-carboxylic acid (4) afforded diastereomeric mixtures of the esters 5-8 and the amides 9 and 10. Pure diastereomers of 3 were synthesized with 4a and 4b, which inhibited the binding of colchicine by 60%. In the presence of calf brain microtubular protein, the colchifoline spin labels underwent reduction of the nitroxide group, which precluded their use to study the topography of the colchicine binding site.

  DOI：

  10.1021/jm00378a035

文献信息

• Synthesis and binding to tubulin of colchicine spin probes
  作者：Padam N. Sharma、Arnold Brossi、J. V. Silverton、Colin F. Chignell

  DOI：10.1021/jm00378a035

  日期：1984.12

  Spin probes of deacetylcholchicine (1), 4-(hydroxymethyl)colchicine (2), and colchifoline (3) have been synthesized to study the binding site for colchicine on tubulin. Acylation of 1-3 with (+/-)-2,2,5,5-tetramethyl-1-pyrrolidinyloxy-3-carboxylic acid (4) afforded diastereomeric mixtures of the esters 5-8 and the amides 9 and 10. Pure diastereomers of 3 were synthesized with 4a and 4b, which inhibited the binding of colchicine by 60%. In the presence of calf brain microtubular protein, the colchifoline spin labels underwent reduction of the nitroxide group, which precluded their use to study the topography of the colchicine binding site.