2-去甲基秋水仙碱 | 7336-36-9

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 中文名称: 2-去甲基秋水仙碱
• 英文名称: 2-demethylcolchicine
• 英文别名: 2-O-demethylcolchicine；N-[(7S)-2-hydroxy-1,3,10-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• CAS: 7336-36-9
• 化学式: C₂₁H₂₃NO₆
• 分子量: 385.417
• InChiKey: DPOVAJCRYIUTBD-HNNXBMFYSA-N

物化性质

• 熔点：
  125°C
• 沸点：
  512.62°C (rough estimate)
• 密度：
  1.2875 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-去甲基秋水仙碱 在 硫酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 1,2-diethoxycarbonyl-1,2-didemethylcolchicine
  参考文献：
  名称：

  Muzaffar, Anjum; Chrzanowska, Maria; Brossi, Arnold, Heterocycles, 1989, vol. 28, # 1, p. 365 - 372

  摘要：

  DOI：
• 作为产物：
  描述：

  秋水仙碱 在 硫酸 作用下， 反应 7.0h， 以53%的产率得到2-去甲基秋水仙碱
  参考文献：
  名称：

  环A中带有迈克尔受体部分的秋水仙碱和硫代秋水仙碱衍生物的合成和生物学评价

  摘要：

  我们合成了一系列秋水仙碱和硫代秋水仙碱衍生物，其中环A部分带有迈克尔受体。其中一些化合物在纳摩尔范围内表现出细胞毒性活性，能够有效破坏有丝分裂纺锤体，并导致G2/M期细胞积累，从而引发细胞凋亡。这些衍生物可与微管蛋白秋水仙碱结合位点的半胱氨酸残基共价结合。

  DOI：

  10.1007/s11172-022-3449-7

文献信息

• Biological effects of modified colchicines. Improved preparation of 2-demethylcolchicine, 3-demethylcolchicine, and (+)-colchicine and reassignment of the position of the double bond in dehydro-7-deacetamidocolchicines
  作者：Manfred Roesner、Hans-Georg Capraro、Arthur E. Jacobson、Louise Atwell、Arnold Brossi、Maria A. Iorio、Thomas H. Williams、Robert H. Sik、Colin F. Chignell

  DOI：10.1021/jm00135a005

  日期：1981.3

  A variety of colchicine, demecolcine, and isocolchicine derivatives were examined for their potency in the lymphocytic leukemia P388 screen in mice, for their toxicity in mice, and for their binding to microtubule protein. A qualitatively direct correlation was found between in vivo potency and toxicity; potency appeared to be less well correlated with tubulin binding. The most potent compounds were N-acylated analogues of colchicine and demecolcine. Among the monophenols, only 3-demethylcolchicine showed an appreciable effect in vitro and in vivo and was less toxic than colchicine. Improved methods were found for the preparation of 3- and 2-demethylcolchicine, which involved the use of 85% phosphoric acid and concentrated sulfuric acid, respectively. Decoupling experiments with 1H NMR proved that the double bond of dehydro-7-deacetamidocolchiceine and its derived tropolonic methyl ethers 24 and 25 was in the 5,6 position, rather than the 6,7 position formerly tentatively assigned.
• 2,10-Didemethylcolchicine ? A new alkaloid from Merendera robusta
  作者：B. Ch. Chommadov、M. K. Yusupov、Kh. A. Aslanov

  DOI：10.1007/bf00629833

  日期：——
• Synthesis of two aromatic methylenedioxy-substituted colchicine congeners: elucidation of the structure of cornigerine as 2,3-(methylenedioxy)-2,3-didemethoxycolchicine
  作者：Manfred Roesner、Fu-Lian Hsu、Arnold Brossi

  DOI：10.1021/jo00331a021

  日期：1981.8
• Four new colchicinoids, gloriosamines A–D, from Gloriosa rothschildiana
  作者：Mariko Kitajima、Akiko Tanaka、Noriyuki Kogure、Hiromitsu Takayama

  DOI：10.1016/j.tetlet.2007.11.061

  日期：2008.1

  Four new colchicinoids, gloriosamines A-D, were isolated from the aerial parts of Gloriosa rothschildiana. The structure of gloriosamine A, including the absolute configuration, was determined by chemical conversion from colchicine. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.