3-(3,4-diacetoxyphenyl)-2-isocyanato-propionic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(3,4-diacetoxyphenyl)-2-isocyanato-propionic acid
• 英文别名: Methyl 3-(3,4-diacetyloxyphenyl)-2-isocyanatopropanoate；methyl 3-(3,4-diacetyloxyphenyl)-2-isocyanatopropanoate
• 化学式: C₁₅H₁₅NO₇
• 分子量: 321.287
• InChiKey: JHSLQASCLHRRBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(3,4-diacetoxyphenyl)-2-isocyanato-propionic acid 在 盐酸 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 22.0h， 生成 methyl (2S)-2-[[5-[(E)-2-cyano-3-(diethylamino)-3-oxoprop-1-enyl]-2-hydroxy-3-nitrophenoxy]carbonylamino]-3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  Design and Synthesis of a Novel L-Dopa−Entacapone Codrug

  摘要：

  A novel codrug, in which L-Dopa and entacapone are linked via a biodegradable carbamate spacer to form a single chemical entity, was synthesized and studied kinetically. This carbamate codrug provides adequate stability [t(1/2) = 12.1 h (pH 1.2); 1.4 h (pH 5.0); 1.1 h (pH 7.4)] against chemical hydrolysis but rapidly hydrolyzes to L-Dopa and entacapone in liver homogenate (t(1/2) = 7 min; pH 7.4) at 37 degreesC. The therapeutical potential of this novel codrug is discussed.

  DOI：

  10.1021/jm010980d
• 作为产物：
  描述：

  (+)-3,4-diacetyloxy-L-phenylalanine methyl ester hydrochloride 、 氯甲酸三氯甲酯 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 3-(3,4-diacetoxyphenyl)-2-isocyanato-propionic acid
  参考文献：
  名称：

  Design and Synthesis of a Novel L-Dopa−Entacapone Codrug

  摘要：

  A novel codrug, in which L-Dopa and entacapone are linked via a biodegradable carbamate spacer to form a single chemical entity, was synthesized and studied kinetically. This carbamate codrug provides adequate stability [t(1/2) = 12.1 h (pH 1.2); 1.4 h (pH 5.0); 1.1 h (pH 7.4)] against chemical hydrolysis but rapidly hydrolyzes to L-Dopa and entacapone in liver homogenate (t(1/2) = 7 min; pH 7.4) at 37 degreesC. The therapeutical potential of this novel codrug is discussed.

  DOI：

  10.1021/jm010980d

文献信息

• Pharmaceutical compounds
  申请人：Jarvinen Tomi

  公开号：US20050059608A1

  公开（公告）日：2005-03-17

  Compounds of formula (I), wherein E, G, T, R d , R e , and R f are as defined in the disclosure, release levodopa and a COMT inhibitor so that they can be used for the treatment of diseases or conditions, wherein levodopa and inhibition of COMT are indicated to be useful.

  公式（I）的化合物，其中E，G，T，Rd，Re和Rf的定义如披露所述，释放左旋多巴和COMT抑制剂，因此它们可用于治疗疾病或病况，其中左旋多巴和COMT抑制剂的使用被认为是有用的。
• NEW PHARMACEUTICAL COMPOUNDS
  申请人：ORION CORPORATION

  公开号：EP1453793A2

  公开（公告）日：2004-09-08
• [EN] NEW PHARMACEUTICAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES PHARMACEUTIQUES
  申请人：ORION CORP

  公开号：WO2003043974A2

  公开（公告）日：2003-05-30

  Compounds of formula (I), wherein E, G, T, Rd, Re, and Rf are as defined in claims, release levodopa and a COMT inhibitor so that they can be used for the treatment of diseases or conditions, wherein levodopa and inhibition of COMT are indicated to be useful.