N-{4-(aminomethyl)phenyl}-5-(dimethylamino)naphthalene-1-sulfonamide hydrochloride | 1222084-09-4

• 英文名称: N-{4-(aminomethyl)phenyl}-5-(dimethylamino)naphthalene-1-sulfonamide hydrochloride
• CAS: 1222084-09-4
• 化学式: C₁₉H₂₁N₃O₂S*ClH
• 分子量: 391.922
• InChiKey: LNANJFUYMUHDQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  75.43
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-O-hemisuccinylpodophyllotoxin 、 N-{4-(aminomethyl)phenyl}-5-(dimethylamino)naphthalene-1-sulfonamide 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66%的产率得到podophyllotoxinyl 4-[4-{5-(dimethylamino)naphthalene-1-sulfonamido}benzylamino]-4-oxobutanoate
  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 4-(5-(dimethylamino)naphthalene-1-sulfonamido)benzylcarbamate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到N-{4-(aminomethyl)phenyl}-5-(dimethylamino)naphthalene-1-sulfonamide 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