(R)-N-(4-aminobutyl)-2-(6-methoxynaphthalen-2-yl)propanamide hydrochloride | 1222084-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-N-(4-aminobutyl)-2-(6-methoxynaphthalen-2-yl)propanamide hydrochloride
• CAS: 1222084-07-2
• 化学式: C₁₈H₂₄N₂O₂*ClH
• 分子量: 336.862
• InChiKey: BVAUOCDYQZUAQW-BTQNPOSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  64.35
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-O-hemisuccinylpodophyllotoxin 、 (R)-N-(4-aminobutyl)-2-(6-methoxynaphthalen-2-yl)propanamide hydrochloride 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以64%的产率得到(S)-N-{(succinylpodophyllotoxinyl)but-4-yl}-2-(6-methoxynaphthalen-2-yl)propanamide
  参考文献：
  名称：

  Podophyllotoxin analogues active versus Trypanosoma brucei

  摘要：

  In an effort to discover novel anti-trypanosomal compounds, a series of podophyllotoxin analogues coupled to non-steroidal anti-inflammatory drugs (NSAIDs) has been synthesized and evaluated for activity versus Trypanosoma brucei and a panel of human cell lines, revealing compounds with low nano-molar potencies. It was discovered that coupling of NSAIDs to podophyllotoxin increased the potencies of both compounds over 1300-fold. The compounds were shown to be cytostatic in nature and seem to act via de-polymerization of tubulin in a manner consistent with the known activities of podophyllotoxin. The potencies against T. brucei correlated directly with Log P values of the compounds, suggesting that the conjugates are acting as hydrophobic tags allowing podophyllotoxin to enter the cell. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.009
• 作为产物：
  描述：

  t-butyl (R)-4-(2-(6-methoxynaphthalen-2-yl)propanamido)butylcarbamate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到(R)-N-(4-aminobutyl)-2-(6-methoxynaphthalen-2-yl)propanamide hydrochloride
  参考文献：
  名称：

  Podophyllotoxin analogues active versus Trypanosoma brucei

  摘要：

  In an effort to discover novel anti-trypanosomal compounds, a series of podophyllotoxin analogues coupled to non-steroidal anti-inflammatory drugs (NSAIDs) has been synthesized and evaluated for activity versus Trypanosoma brucei and a panel of human cell lines, revealing compounds with low nano-molar potencies. It was discovered that coupling of NSAIDs to podophyllotoxin increased the potencies of both compounds over 1300-fold. The compounds were shown to be cytostatic in nature and seem to act via de-polymerization of tubulin in a manner consistent with the known activities of podophyllotoxin. The potencies against T. brucei correlated directly with Log P values of the compounds, suggesting that the conjugates are acting as hydrophobic tags allowing podophyllotoxin to enter the cell. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.009