(L)-1,8-bis[2-(N-valine methyl ester)acetamido]anthraquinone | 1228598-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (L)-1,8-bis[2-(N-valine methyl ester)acetamido]anthraquinone
• 英文别名: methyl (2S)-2-[[2-[[8-[[2-[[(2S)-1-methoxy-3-methyl-1-oxobutan-2-yl]amino]acetyl]amino]-9,10-dioxoanthracen-1-yl]amino]-2-oxoethyl]amino]-3-methylbutanoate
• CAS: 1228598-31-9
• 化学式: C₃₀H₃₆N₄O₈
• 分子量: 580.638
• InChiKey: HSTLASRKLQIOPK-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,8-二氨基蒽醌 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (L)-1,8-bis[2-(N-valine methyl ester)acetamido]anthraquinone
  参考文献：
  名称：

  Design, synthesis and evaluation of telomerase inhibitory, hTERT repressing, and anti-proliferation activities of symmetrical 1,8-disubstituted amidoanthraquinones

  摘要：

  A series of symmetrical disubstituded 1,8-diamidoanthraquinones were synthesized and evaluated for anti-proliferation, telomerase inhibitory by TRAP assay, and hTERT expression by SEAP assay. All of the compounds tested, except for compounds 3a and 3s were selected by the NCI screening system. In addition, compounds 4e and 4k exhibited inhibitory effects on telomerase activity. Taken together, our findings indicated that the analysis of cytotoxicity and telomerase inhibition might provide information applicable for further developing potential telomerase targeting strategy. Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.044

文献信息

• ANTI-CANCER COMPOUND AND MANUFACTURING METHOD THEREOF
  申请人：HUANG Hsu-Shan

  公开号：US20100145070A1

  公开（公告）日：2010-06-10

  Anti-cancer compounds and manufacturing methods thereof are disclosed. The anti-cancer compounds are 1,8-diamidoanthraquinone derivatives with amino compounds. The manufacturing method includes the steps of: add 1,8-bis(chloroacetamido)anthraquinone or 1,8-bis(3-chloropropionamido)-anthraquinone with amino compounds, catalysts, and dehydrated dimethylformamide (DMF) to form a mixture and react with one another. Then by purification and recrystallization, the anti-cancer compounds are obtained. The anti-cancer compounds of the present invention are compounds with whole new structure that overcome serious cardiac toxicity of the conventional anti-cancer drug-doxorubincin.

  揭示了抗癌化合物及其制造方法。这些抗癌化合物是含氨基化合物的1,8-二氨基蒽醌衍生物。制造方法包括以下步骤：将1,8-双(氯乙酰胺基)蒽醌或1,8-双(3-氯丙酰胺基)-蒽醌与氨基化合物、催化剂和脱水二甲基甲酰胺（DMF）混合反应。然后通过纯化和再结晶，得到抗癌化合物。本发明的抗癌化合物是具有全新结构的化合物，克服了传统抗癌药物多柔比星的严重心脏毒性。
• Design, synthesis and evaluation of telomerase inhibitory, hTERT repressing, and anti-proliferation activities of symmetrical 1,8-disubstituted amidoanthraquinones
  作者：Chia-Chung Lee、Kuo-Feng Huang、Deh-Ming Chang、Jung-Jung Hsu、Fong-Chun Huang、Kai-Ning Shih、Chun-Liang Chen、Tsung-Chih Chen、Ruei-Huei Chen、Jing-Jer Lin、Hsu-Shan Huang

  DOI：10.1016/j.ejmech.2012.01.044

  日期：2012.4

  A series of symmetrical disubstituded 1,8-diamidoanthraquinones were synthesized and evaluated for anti-proliferation, telomerase inhibitory by TRAP assay, and hTERT expression by SEAP assay. All of the compounds tested, except for compounds 3a and 3s were selected by the NCI screening system. In addition, compounds 4e and 4k exhibited inhibitory effects on telomerase activity. Taken together, our findings indicated that the analysis of cytotoxicity and telomerase inhibition might provide information applicable for further developing potential telomerase targeting strategy. Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.