4-aminoanilino-4-hydroxyphenethylaminomethanone | 393511-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-aminoanilino-4-hydroxyphenethylaminomethanone
• 英文别名: 1-(4-Aminophenyl)-3-[2-(4-hydroxyphenyl)ethyl]urea
• CAS: 393511-89-2
• 化学式: C₁₅H₁₇N₃O₂
• 分子量: 271.319
• InChiKey: UJKHAIJQWPATDC-UHFFFAOYSA-N

物化性质

• 沸点：
  500.6±50.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87.4
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-aminoanilino-4-hydroxyphenethylaminomethanone 在 D₂₀ 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 氘代二甲亚砜 、 水 为溶剂， 反应 185.0h， 生成
  参考文献：
  名称：

  Synthesis and analysis of urea and carbamate prodrugs as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT)

  摘要：

  The suitability of 4-di(2-chloroethyl)aminoanilino-4-hydroxyphenethylaminomethanone 2 to act as a prodrug for melanocyte-directed enzyme prodrug therapy (MDEPT) is assessed. Thus its synthesis, ability to generate a cytotoxic agent upon exposure to tyrosinase, and stability within different sera are reported. A comparison is made to illustrate that the new urea prodrug 2 is a more suitable candidate for MDEPT than the corresponding carbamate prodrug 1. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00097-4
• 作为产物：
  描述：

  对羟基苯乙胺 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-aminoanilino-4-hydroxyphenethylaminomethanone
  参考文献：
  名称：

  Synthesis and analysis of urea and carbamate prodrugs as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT)

  摘要：

  The suitability of 4-di(2-chloroethyl)aminoanilino-4-hydroxyphenethylaminomethanone 2 to act as a prodrug for melanocyte-directed enzyme prodrug therapy (MDEPT) is assessed. Thus its synthesis, ability to generate a cytotoxic agent upon exposure to tyrosinase, and stability within different sera are reported. A comparison is made to illustrate that the new urea prodrug 2 is a more suitable candidate for MDEPT than the corresponding carbamate prodrug 1. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00097-4

文献信息

• Phenylethylamine derivatives and their use in the treatment of melanoma
  申请人：——

  公开号：US20040029967A1

  公开（公告）日：2004-02-12

  Novel mono- and dihydroxy phenylethylamine derivatives useful in treating melanoma are provided having the formulae (Ia, Ib or Ic). In the above formulae, R a is hydrogen or —COOR b, R b is hydrogen or C 1-6 alkyl; R e and R e independently represent hydrogen and hydroxy, R f is hydrogen, C 1-4? alkyl or halogen, X is —CHOH—, —CH 2 -oxygen or sulphur, m is zero or 1, W is oxygen or sulphur, and —ODrug, —NHDrug and —N(Drug) 2 each represent a residue of a therapeutically active agent. The above compounds are prodrugs which are inactive until metabolised by enzymes expressed by host melanoma cells. The invention allows a greater amount of active agent to be used while reducing systemic side effects. 1

  提供了用于治疗黑色素瘤的新型单氢和二羟基苯乙胺衍生物，其化学式为（Ia、Ib或Ic）。在上述化学式中，R是氢或—COORb，Rb是氢或C1-6烷基；Re和Re独立表示氢和羟基，Rf是氢、C1-4烷基或卤素，X是—CHOH—、—CH2-氧或硫，m为零或1，W是氧或硫，而—ODrug、—NHDrug和—N（Drug）2分别表示治疗活性剂的残基。上述化合物是一种前药，在被宿主黑色素瘤细胞表达的酶代谢之前是无效的。该发明允许使用更多的活性剂而减少全身副作用。
• [EN] PHENYLETHYLAMINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF MELANOMA<br/>[FR] DERIVES DE PHENYLETHYLAMINE ET LEUR UTILISATION DANS LE TRAITEMENT DE MELANOME
  申请人：RILEY PATRICK ANTHONY

  公开号：WO2002008174A1

  公开（公告）日：2002-01-31

  Novel mono- and dihydroxy phenylethylamine derivatives useful in treating melanoma are provided having the formulae (Ia, Ib or Ic). In the above formulae, Ra is hydrogen or -COORb, Rb is hydrogen or C¿1-6? alkyl; R?e and Re¿ independently represent hydrogen and hydroxy, Rf is hydrogen, C¿1-4? alkyl or halogen, X is -CHOH-, -CH2-oxygen or sulphur, m is zero or 1, W is oxygen or sulphur, and -ODrug, -NHDrug and -N(Drug)2 each represent a residue of a therapeutically active agent. The above compounds are prodrugs which are inactive until metabolised by enzymes expressed by host melanoma cells. The invention allows a greater amount of active agent to be used while reducing systemic side effects.

  本发明提供了一种在治疗黑色素瘤方面有用的新型单和双羟基苯乙胺衍生物，其化学式为（Ia，Ib或Ic）。在上述化学式中，Ra为氢或-COORb，Rb为氢或C1-6烷基；Re和Re'独立地表示氢和羟基，Rf为氢，C1-4烷基或卤素，X为-CHOH-，-CH2-氧或硫，m为零或1，W为氧或硫，-ODrug，-NHDrug和-N（Drug）2分别表示治疗活性剂的残基。上述化合物是前药，在被宿主黑色素瘤细胞表达的酶代谢之前是不活性的。本发明允许使用更多的活性剂而减少全身副作用。
• PHENYLETHYLAMINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF MELANOMA
  申请人：Riley, Patrick Anthony

  公开号：EP1303481A1

  公开（公告）日：2003-04-23
• US7183319B2
  申请人：——

  公开号：US7183319B2

  公开（公告）日：2007-02-27
• Synthesis and analysis of urea and carbamate prodrugs as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT)
  作者：Allan M. Jordan、Tariq H. Khan、Hugh Malkin、Helen M.I. Osborn

  DOI：10.1016/s0968-0896(02)00097-4

  日期：2002.8

  The suitability of 4-di(2-chloroethyl)aminoanilino-4-hydroxyphenethylaminomethanone 2 to act as a prodrug for melanocyte-directed enzyme prodrug therapy (MDEPT) is assessed. Thus its synthesis, ability to generate a cytotoxic agent upon exposure to tyrosinase, and stability within different sera are reported. A comparison is made to illustrate that the new urea prodrug 2 is a more suitable candidate for MDEPT than the corresponding carbamate prodrug 1. (C) 2002 Elsevier Science Ltd. All rights reserved.