N-[(7S)-1,2,3-trimethoxy-9-oxo-10-(piperidin-1-yl)-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide | 165069-84-1

• 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-[(7S)-1,2,3-trimethoxy-9-oxo-10-(piperidin-1-yl)-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
• 英文别名: N-[(7S)-1,2,3-Trimethoxy-9-oxo-10-(1-piperidinyl)-5,6,7,9-tetrahydrobenzo[A]heptalen-7-YL]acetamide；N-[(7S)-1,2,3-trimethoxy-9-oxo-10-piperidin-1-yl-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• CAS: 165069-84-1
• 化学式: C₂₆H₃₂N₂O₅
• mdl: MFCD02183324
• 分子量: 452.55
• InChiKey: WXVFMHNWBFGZHR-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(7S)-1,2,3-trimethoxy-9-oxo-10-(piperidin-1-yl)-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide 在 硫酸 、 水 作用下， 反应 5.0h， 以72%的产率得到
  参考文献：
  名称：

  Synthesis and Antitumour Activity of Novel Colchicine C-10 Derivatives

  摘要：

  一系列新的秋水仙素C-10衍生物（2a-i，3a-h）通过将10-甲氧基替换为NR2和SCH3合成，旨在确定它们的细胞毒活性。这些化合物以良好产率合成，所有新合成化合物的结构根据其IR、1H NMR和元素分析确定。合成的化合物通过MTT assay在体外对四种人癌细胞株进行了抗肿瘤活性测试。发现许多衍生物显示出显著活性，特别是化合物2a和2b展现出比秋水仙素更强的细胞毒活性。

  DOI：

  10.14233/ajchem.2014.16892
• 作为产物：
  描述：

  哌啶 、 秋水仙碱 以 甲醇 为溶剂， 以81%的产率得到N-[(7S)-1,2,3-trimethoxy-9-oxo-10-(piperidin-1-yl)-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
  参考文献：
  名称：

  Colchicine derivatives with potent anticancer activity and reduced P-glycoprotein induction liability

  摘要：

  已经确定了几种减少P-糖蛋白诱导责任的秋水仙碱衍生物。

  DOI：

  10.1039/c5ob00406c

文献信息

• Simplified, high-yield regioselective synthesis of 10-aminocolchicides and 2-aminotropones
  作者：Marino Cavazza、Francesco Pietra

  DOI：10.1016/0040-4039(95)00499-3

  日期：1995.5

  Treatment of colchiceine with BF3OEt2, followed by evaporation, addition of DMSO and a secondary amine like piperidine, or sterically hindered like 2-methylpiperidine, was found to result in rapid, quantitative replacement of the hydroxyl group at C-10 or C-9 by the amine to give the 10-aminocolchicide/9-aminoisocolchicide or with high regiospecificity for 10-aminocolchicide; the products could be

  发现用BF 3 OEt 2处理秋水仙碱，然后蒸发，添加DMSO和仲胺（如哌啶）或空间受阻胺（如2-甲基哌啶）可快速，定量地取代C-10或C处的羟基通过胺-9，得到10-氨基杀菌剂/ 9-氨基异杀菌剂或对10-氨基杀菌剂具有高区域特异性的化合物；产品可以轻松分离，方法学扩展到托酚酮和/或伯胺。
• Formaldehyd-O-oxid und Colchicine: ein eleganter Zugang zu Allocolchicinen
  作者：Ulrich Dilger、B�rbel Franz、Herbert R�ttele、Gerhard Schr�der、Rainer Herges

  DOI：10.1002/prac.19983400510

  日期：——

  Tropone is a structural unit of numerous natural products i.e. imerubrine, harringtonolide and colchicine (2). It is of interest to study the selectivity of formaldehyde-O-oxide (1) with respect to these polyfunctional tropone derivatives. We report about the reactions of 1 with colchicine (2) and the colchicine derivatives 5, 8, 11, 14, 17, 20 under ozone free conditions. The fragmentation of the spiroozonides 3, 6, 9, 12, 15, 18, 21 via the activated complexes 3a, 6a, 9a, 12a, 15a, 18a, 21a opens up an elegant route to the allocolchicines 4, 7, 10, 13, 16, 19.
• ipso-vs. tele-Nucleophilic substitution by piperidine on isocolchicides and colchicides bearing an α-leaving group
  作者：Marino Cavazza、Francesco Pietra

  DOI：10.1039/p19950002657

  日期：——

  Product studies of the reactions of piperidine with colchicides carrying a C-10 nucleofugic group show that only ipso substitution occurs. For isocolchicides carrying an X nucleofugic group at C-9, similar behaviour was observed for X = F, OTs or OMe, while for X = SMe, SOMe or Cl tele substitution (at C-ll) competes with ipso substitution. These results together with the observation that the reaction rates for the two series are similar, may be useful in guiding the refunctionalization of similar compounds.
• Synthesis and Antitumour Activity of Novel Colchicine C-10 Derivatives
  作者：Li Hong Shen、Le Zhang、Hai Xian Wang、Xin Wang、Gai Jiao Zhang

  DOI：10.14233/ajchem.2014.16892

  日期：——

  A series of new colchicine C-10 derivatives (2a-i, 3a-h) were synthesized by replacement of the 10-methoxy with NR2 and SCH3 in order to determine their cytotoxic activity. The compounds were synthesized in good yield and the structures of all newly synthesized compounds were established on the basis of their IR, 1H NMR and elemental analysis. The synthesized compounds were tested in vitro antitumor activity against four human cancer cell lines by MTT assay. It was found that many of the derivatives displayed significant activity, particularly, compound 2a and 2b showed more potent cytotoxic activities than colchicine.

  一系列新的秋水仙素C-10衍生物（2a-i，3a-h）通过将10-甲氧基替换为NR2和SCH3合成，旨在确定它们的细胞毒活性。这些化合物以良好产率合成，所有新合成化合物的结构根据其IR、1H NMR和元素分析确定。合成的化合物通过MTT assay在体外对四种人癌细胞株进行了抗肿瘤活性测试。发现许多衍生物显示出显著活性，特别是化合物2a和2b展现出比秋水仙素更强的细胞毒活性。
• Colchicine derivatives with potent anticancer activity and reduced P-glycoprotein induction liability
  作者：Baljinder Singh、Ashok Kumar、Prashant Joshi、Santosh K. Guru、Suresh Kumar、Zahoor A. Wani、Girish Mahajan、Aashiq Hussain、Asif Khurshid Qazi、Ajay Kumar、Sonali S. Bharate、Bishan D. Gupta、Parduman R. Sharma、Abid Hamid、Ajit K. Saxena、Dilip M. Mondhe、Shashi Bhushan、Sandip B. Bharate、Ram A. Vishwakarma

  DOI：10.1039/c5ob00406c

  日期：——

  Colchicine derivatives with reduced P-gp induction liability have been identified.

  已经确定了几种减少P-糖蛋白诱导责任的秋水仙碱衍生物。