{2'-(3'',4''-dihydroxyphenyl)ethyl} carbamic acid p-(bis-2-chloroethylamino)phenyl ester | 209158-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: {2'-(3'',4''-dihydroxyphenyl)ethyl} carbamic acid p-(bis-2-chloroethylamino)phenyl ester
• 英文别名: [4-[bis(2-chloroethyl)amino]phenyl] N-[2-(3,4-dihydroxyphenyl)ethyl]carbamate
• CAS: 209158-08-7
• 化学式: C₁₉H₂₂Cl₂N₂O₄
• 分子量: 413.301
• InChiKey: NYMLZRIYPYFHPB-UHFFFAOYSA-N

物化性质

• 沸点：
  610.3±55.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  82
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4--O-benzylphenol 在 palladium on activated charcoal 盐酸 、 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 73.0h， 生成 {2'-(3'',4''-dihydroxyphenyl)ethyl} carbamic acid p-(bis-2-chloroethylamino)phenyl ester
  参考文献：
  名称：

  Melanocyte-directed enzyme prodrug therapy (MDEPT): development of a targeted treatment for malignant melanoma

  摘要：

  A novel prodrug rationally designed to function as a tyrosinase substrate has been synthesised to allow targeted treatment of malignant melanoma. This agent has been evaluated for tyrosinase-mediated drug release, and has been shown to act in the desired manner. Furthermore, differential cytotoxicity has been demonstrated in cell lines which express tyrosinase and those which do not.

  DOI：

  10.1016/s0968-0896(99)00126-1

文献信息

• Melanocyte-Directed enzyme prodrug therapy (MDEPT)
  作者：Allan M. Jordan、Tariq H. Khan、Hugh Malkin、Helen M.I. Osborn、Andrew Photiou、Patrick A. Riley

  DOI：10.1016/s0968-0896(01)00039-6

  日期：2001.6

  Evaluation of second generation prodrugs for MDEPT, by oximetry, has highlighted structural properties that are advantageous and disadvantageous for efficient oxidation using mushroom tyrosinase. In particular, a sterically undemanding prodrug bis-(2-chloroethyl)amino-4-hydroxyphenylaminomethanone 28 was synthesised and found to be oxidised by mushroom tyrosinase at a superior rate to tyrosine methyl ester, the carboxylic acid of which is the natural substrate for tyrosinase. The more sterically demanding phenyl mustard prodrugs 9 and 10 were oxidised by mushroom tyrosinase at a similar rate to tyrosine methyl ester. In contrast, tyramine chain elongation via heteroatom insertion was detrimental and the rate of mushroom tyrosinase oxidation of phenyl mustard prodrugs 21 and 22 decreased by 10 nanomol/min. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Melanocyte-directed enzyme prodrug therapy (MDEPT): development of a targeted treatment for malignant melanoma
  作者：Allan M. Jordan、Tariq H. Khan、Helen M.I. Osborn、Andrew Photiou、Patrick A. Riley

  DOI：10.1016/s0968-0896(99)00126-1

  日期：1999.9

  A novel prodrug rationally designed to function as a tyrosinase substrate has been synthesised to allow targeted treatment of malignant melanoma. This agent has been evaluated for tyrosinase-mediated drug release, and has been shown to act in the desired manner. Furthermore, differential cytotoxicity has been demonstrated in cell lines which express tyrosinase and those which do not.