N-benzoyldeacetylcolchiceine | 14686-58-9

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: N-benzoyldeacetylcolchiceine
• 英文别名: N-((S)-10-hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-benzamide；N-((S)-10-Hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-benzamid；(S)-7-Benzoylamino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-on；Benzo(a)heptalen-9(5H)-one, 7-benzamido-6,7-dihydro-10-hydroxy-1,2,3-trimethoxy-；N-[(7S)-10-hydroxy-1,2,3-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]benzamide
• CAS: 14686-58-9
• 化学式: C₂₆H₂₅NO₆
• 分子量: 447.488
• InChiKey: IHMBFORMNABTCS-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 N-benzoyldeacetylcolchiceine 在 甲醇 、 乙醚 作用下， 生成 (S)-6,7-二氢-1,2,3,10-四甲氧基-7-(苯甲酰基氨基)苯并[a]庚搭烯-9(5H)-酮
  参考文献：
  名称：

  Santavy, Chemicke Listy, 1952, vol. 46, p. 280,284

  摘要：

  DOI：
• 作为产物：
  描述：

  (7S)-7-氨基-1,2,3,10-四甲氧基-6,7-二氢-5H-苯并[g]庚搭烯-9-酮 在 吡啶 、 盐酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 18.0h， 生成 N-benzoyldeacetylcolchiceine
  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

文献信息

• Cook et al., Journal of the Chemical Society, 1950, p. 537,542
  作者：Cook et al.

  DOI：——

  日期：——
• COLCHICINE. STRUCTURE OF WINDAUS' ANHYDRIDE^1,2
  作者：E. C. Horning、M. G. Horning、J. Koo、M. S. Fish、J. A. Parker、G. N. Walker、R. M. Horowitz、G. E. Ullyot

  DOI：10.1021/ja01166a536

  日期：1950.10
• Santavy, Chemicke Listy, 1952, vol. 46, p. 280,284
  作者：Santavy

  DOI：——

  日期：——
• Biological effects of modified colchicines. 2. Evaluation of catecholic colchicines, colchifolines, colchicide, and novel N-acyl- and N-aroyldeacetylcolchicines
  作者：Arnold Brossi、Padam N. Sharma、Louise Atwell、Arthur E. Jacobson、Maria A. Iorio、Marisa Molinari、Colin F. Chignell

  DOI：10.1021/jm00364a006

  日期：1983.10

  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.