Desacetamido-colchicein | 5320-47-8

• 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: Desacetamido-colchicein
• 英文别名: Desacetamidocolchicin；10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one
• CAS: 5320-47-8
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: PEXRTDXKYWOAEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Desacetamido-colchicein 在 甲醇 、 四氯化碳 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 乙醚 作用下， 生成 (+/-)7-Azido-desacetamidoisocolchicin
  参考文献：
  名称：

  THE TOTAL SYNTHESIS OF COLCHICINE

  摘要：

  DOI：

  10.1021/ja01532a070
• 作为产物：
  描述：

  deacetamidoisocolchicide 在 氢氧化钾 、 肼 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 Desacetamido-colchicein
  参考文献：
  名称：

  Thermal, four-carbon + three-carbon cycloaddition reaction of cyclopropenone ketals. Total synthesis of deacetamidocolchiceine: formal total synthesis of colchicine

  摘要：

  DOI：

  10.1021/jo00218a042

文献信息

• Total synthesis of colchicine modelled on a biogenetic theory
  作者：A.I. Scott、F. McCapra、R.L. Buchanan、A.C. Day、D.W. Young

  DOI：10.1016/s0040-4020(01)96977-7

  日期：1965.1

  A five step synthesis of desacetamidocolchiceine (XLVI) is described in which rings A and C are joined by oxidative coupling of the tropolone system. This completes a biogenetic-type total synthesis of colchicine (I).

  描述了五步合成的去乙酰氨基多西奇碱（XLVI），其中环A和C通过对酮系统的氧化偶联而连接在一起。这样就完成了秋水仙碱（I）的生物遗传型全合成。
• Synthetic Study of Colchicine
  作者：Michiharu Kato、Fusao Kido、Ming-Der Wu、Akira Yoshikoshi

  DOI：10.1246/bcsj.47.1516

  日期：1974.6

  An efficient route based upon solvolytic fragmentation of a cyclopentadiene-dichloroketene adduct 4c has been investigated for the synthesis of trimethoxyphenylpropyltropolone 2b, a synthetic intermediate of colchicine 1a. Attempted synthesis of the corresponding unsaturated tropolones 8a and 10 is also discussed.

  我们研究了一条基于环戊二烯-二氯乙烯加合物 4c 溶解破碎的高效路线，用于合成三甲氧基苯基丙基伯罗酮 2b（秋水仙碱 1a 的合成中间体）。此外，还讨论了相应的不饱和三苯乙烯酮 8a 和 10 的尝试合成。
• Discovery of structurally simplified analogs of colchicine as an immunosuppressant
  作者：Dong-Jo Chang、Wan-Joo Kim

  DOI：10.1016/j.bmcl.2014.05.007

  日期：2014.7

  We have discovered a new class of colchicine-derived therapeutic agents for immune diseases including rejection of organ-transplantation and autoimmune disease. Compound 2, which had been developed to overcome poor pharmacokinetic properties of compound 1, a first-generation colchicine analog, turned out to show toxicity such as intestinal toxicity and loss of weight during in vivo tests. The deletion of 7-carboxamide group and middle ring-truncation in colchicine allowed us to have structurally simplified analogs with strong immunosuppressive activity. Herein, we report non-alkaloid tricyclic compound 7 and 12 as immunosuppressants which exhibited a strong immunosuppressive in vivo efficacy on the T-dependent antibody response, the Zymosan A-induced arthritis model and the Carrageenan-induced edema model. Compound 7 and 12 revealed less toxicity than the previous lead compound 2, and their minimum lethal doses (MLD) were proved to exceed 100 mg/kg. (C) 2014 Elsevier Ltd. All rights reserved.
• Jochum, Clemens; Gasteiger, Johann; Ugi, Ivar, Angewandte Chemie, 1980, vol. 92, # 7, p. 503 - 513
  作者：Jochum, Clemens、Gasteiger, Johann、Ugi, Ivar

  DOI：——

  日期：——
• Thermal reactions of cyclopropenone ketals. Application of the cycloaddition reactions of delocalized singlet vinylcarbenes: three-carbon 1,1-/1,3-dipoles. An alternative synthesis of deacetamidocolchiceine: formal total synthesis of colchicine
  作者：Dale L. Boger、Christine E. Brotherton

  DOI：10.1021/ja00281a042

  日期：1986.10