(R)-[1'-amino-2'-hydroxy-2'-(4''-hydroxyphenyl)propionic acid methyl ester]-carbamic acid p-(bis-2-chloroethylamino)phenyl ester | 371754-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-[1'-amino-2'-hydroxy-2'-(4''-hydroxyphenyl)propionic acid methyl ester]-carbamic acid p-(bis-2-chloroethylamino)phenyl ester
• 英文别名: [4-[bis(2-chloroethyl)amino]phenyl] N-[(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-N-methylcarbamate
• CAS: 371754-23-3
• 化学式: C₂₀H₂₄Cl₂N₂O₅
• 分子量: 443.327
• InChiKey: YYETUTTVLNIAKM-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4--O-benzylphenol 在 盐酸 、 甲基磺酰氯 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 73.83h， 生成 (R)-[1'-amino-2'-hydroxy-2'-(4''-hydroxyphenyl)propionic acid methyl ester]-carbamic acid p-(bis-2-chloroethylamino)phenyl ester
  参考文献：
  名称：

  Melanocyte-Directed enzyme prodrug therapy (MDEPT)

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(01)00039-6

文献信息

• US7183319B2
  申请人：——

  公开号：US7183319B2

  公开（公告）日：2007-02-27
• 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.