4-oxo-4-[[(7S)-1,2,3-trimethoxy-10-(methylamino)-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]amino]butanoic acid | 1312592-31-6

• 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: 4-oxo-4-[[(7S)-1,2,3-trimethoxy-10-(methylamino)-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]amino]butanoic acid
• CAS: 1312592-31-6
• 化学式: C₂₄H₂₈N₂O₇
• 分子量: 456.496
• InChiKey: YDAOKCMFFOVXGD-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-oxo-4-[[(7S)-1,2,3-trimethoxy-10-(methylamino)-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]amino]butanoic acid 在 silver nitrate (1-) 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 20.0h， 生成 2-nitrooxyethyl 4-oxo-4-[[(7S)-1,2,3-trimethoxy-10-(methylamino)-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]amino]butanoate
  参考文献：
  名称：

  Synthesis and evaluation of nitrate derivatives of colchicine as anticancer agents

  摘要：

  To search for more potent antitumor agent, a series of novel nitric oxide-donating colchicine (Col) derivatives (6a-f, 8a and b) were synthesized by coupling nitrates with N-methyl colchiceinamide. Their cytotoxicity against four human cancer cell lines in vitro were evaluated by MTT assay. It was found that many of the derivatives displayed significant activity, particularly, compounds 6c, 8a and 8b showed more potent cytotoxic activities than Col. (C) 2010 Li Hong Shen. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.12.037
• 作为产物：
  描述：

  N-methyl colchiceinamide 在 吡啶 、 硫酸 作用下， 以 水 为溶剂， 反应 10.0h， 生成 4-oxo-4-[[(7S)-1,2,3-trimethoxy-10-(methylamino)-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]amino]butanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of nitrate derivatives of colchicine as anticancer agents

  摘要：

  To search for more potent antitumor agent, a series of novel nitric oxide-donating colchicine (Col) derivatives (6a-f, 8a and b) were synthesized by coupling nitrates with N-methyl colchiceinamide. Their cytotoxicity against four human cancer cell lines in vitro were evaluated by MTT assay. It was found that many of the derivatives displayed significant activity, particularly, compounds 6c, 8a and 8b showed more potent cytotoxic activities than Col. (C) 2010 Li Hong Shen. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.12.037

文献信息

• Synthesis and cytotoxic evaluation of new colchicine derivatives bearing 1,3,4-thiadiazole moieties
  作者：Li-Hong Shen、Hong-Yu Li、Hui-Xia Shang、Shu-Ting Tian、Yi-Sheng Lai、Li-Jie Liu

  DOI：10.1016/j.cclet.2013.01.052

  日期：2013.4

  In search of novel anticancer agents, a series of N-methyl colchiceinamide derivatives (7a-7i) containing 1,3,4-thiadiazole moieties were synthesized, and their structures were confirmed by spectral analysis. Cytotoxicity of these compounds was evaluated by MTT assay in vitro against four human tumor cell lines, i.e. A2780, A549, BEL7402, and MCF-7. The results indicated that most of the derivatives showed significant anticancer activities, particularly, compounds 7h and 7i showed more potent cytotoxic activities of all screened cancer cells than colchicine. (C) 2013 Li-Hong Shen. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.