3-O-(N-phenyltetrazolyl)-3-demethylcolchicine | 86436-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-O-(N-phenyltetrazolyl)-3-demethylcolchicine
• 英文别名: N-[(7S)-1,2,10-trimethoxy-9-oxo-3-(1-phenyltetrazol-5-yl)oxy-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• CAS: 86436-32-0
• 化学式: C₂₈H₂₇N₅O₆
• 分子量: 529.552
• InChiKey: GOCQYRYNMGWKOW-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-氯-1-苯基-1H-四唑 、 (-)-3-去甲基秋水仙碱 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 3-O-(N-phenyltetrazolyl)-3-demethylcolchicine
  参考文献：
  名称：

  Biological effects of modified colchicines. 2. Evaluation of catecholic colchicines, colchifolines, colchicide, and novel N-acyl- and N-aroyldeacetylcolchicines

  摘要：

  A series of natural and synthetic colchicine derivatives was examined for their potency in the lymphocytic leukemia P388 screen in mice, for their toxicity in mice, and for their binding to microtubule protein. The natural alkaloids cornigerine and colchifoline and several N,O-substituted analogues of colchifoline were found to be as potent and as toxic as colchicine in the P388 screen with good affinity for tubulin. The 1,2-(methylenedioxy)-substituted isomer of cornigerine was considerably less potent in vivo than could have been anticipated from the in vitro tubulin binding data. Several N-acyl and N-aroyl derivatives prepared from deacetylcolchicine showed high potency in the in vitro and in vivo screens. Colchicide was found to be highly potent in vivo, and N-carbethoxydeacetylcolchicine, a synthetic analogue of colchicine with a N-carbethoxy instead of an N-acetyl function, showed interesting biological properties.

  DOI：

  10.1021/jm00364a006