[3-(3,4-二羟基苯基)-1-氧代-1-苯基甲氧基丙烷-2-基]铵氯化物 | 37178-28-2

• 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
• 中文名称: [3-(3,4-二羟基苯基)-1-氧代-1-苯基甲氧基丙烷-2-基]铵氯化物
• 英文名称: L-3,4-dihydroxyphenylalanine benzyl ester hydrochloride
• 英文别名: 3,4-dihydroxyphenylalanine benzyl ester hydrochloride；DOPA benzyl ester hydrochloride；(2S)-2-amino-3-(3,4-dihydroxyphenyl)benzyl propanoate hydrochloride；benzyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate hydrochloride；3,4-dihydroxy-L-phenylalanine benzyl ester hydrochloride；L-Dopa benzyl ester hydrochloride；benzyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate;hydrochloride
• CAS: 37178-28-2
• 化学式: C₁₆H₁₇NO₄*ClH
• 分子量: 323.776
• InChiKey: SJFUQIANPBDPDH-ZOWNYOTGSA-N

物化性质

• 熔点：
  178-181 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92.8
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [3-(3,4-二羟基苯基)-1-氧代-1-苯基甲氧基丙烷-2-基]铵氯化物 在 盐酸 、 5%-palladium/activated carbon 、 氢气 、 1-羟基苯并三唑 、 1,2-二氯乙烷 作用下， 以 1,4-二氧六环 、 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[(S)-1-Carboxy-2-(3,4-diacetoxyphenyl)-ethylcarbamoyl]-1-methylethyl-ammonium chloride
  参考文献：
  名称：

  Design, synthesis and biological evaluation of peptide derivatives of l-dopa as anti-parkinsonian agents

  摘要：

  A series of dipeptide derivatives of L-dopa were synthesized and investigated for their pharmacological activity using the unilaterally 6-hydroxydopamine (6-OHDA)-lesioned rat as an experimental model of Parkinson's disease. Among them, (S)-isopropyl 2-(2-amino-2-methylpropanamido)-3-(3,4-dihydroxyphenyl) propanoate (4g) was found to be the most active compound, with 106% AUC activity and 149% peak activity of L-dopa after oral administration. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.007
• 作为产物：
  描述：

  左旋多巴 、 苯甲醇 在 盐酸 作用下， 生成 [3-(3,4-二羟基苯基)-1-氧代-1-苯基甲氧基丙烷-2-基]铵氯化物
  参考文献：
  名称：

  Design, synthesis and biological evaluation of peptide derivatives of l-dopa as anti-parkinsonian agents

  摘要：

  A series of dipeptide derivatives of L-dopa were synthesized and investigated for their pharmacological activity using the unilaterally 6-hydroxydopamine (6-OHDA)-lesioned rat as an experimental model of Parkinson's disease. Among them, (S)-isopropyl 2-(2-amino-2-methylpropanamido)-3-(3,4-dihydroxyphenyl) propanoate (4g) was found to be the most active compound, with 106% AUC activity and 149% peak activity of L-dopa after oral administration. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.007

文献信息

• [EN] LEVODOPA-PRODRUGS AND CARBIDOPA-PRODRUGS FOR USE IN THE TREATMENT OF PARKINSON'S DISEASE<br/>[FR] PROMÉDICAMENTS LEVODOPA ET PROMÉDICAMENTS CARBIDOPA POUR LE TRAITEMENT DE LA MALADIE DE PARKINSON
  申请人：MITSUBISHI TANABE PHARMA CORP

  公开号：WO2022191338A1

  公开（公告）日：2022-09-15

  An object of the present invention is to provide a combination medicament useful for treatment of Parkinson's disease. The present invention provides a prophylactic or therapeutic agent for Parkinson's disease, the agent containing a combination medicament containing a levodopa prodrug and a carbidopa prodrug.

  本发明的目的是提供一种组合药物，用于治疗帕金森病。本发明提供了一种预防或治疗帕金森病的药物，该药物含有一种组合药物，其中包含一种左旋多巴前药和一种卡比多巴前药。
• Synthesis and Polymerization Studies of Organic-Soluble Eumelanins
  作者：Kirsten J. Lawrie、Paul Meredith、Ross P. McGeary

  DOI：10.1111/j.1751-1097.2007.00295.x

  日期：2008.5

  AbstractThe isolation, structure determination and chemical characterization of eumelanins has been plagued by their very low solubility in organic solvents. To gain insights into the structure and reactivity of these unusual and important biologic macromolecules and to pave the way for their use in electronics, we have prepared soluble melanins via the synthesis of monomeric precursors containing lipophilic substituents. Two such monomers derived from 5,6‐dihydroxyindole‐2‐carboxylic acid (DHICA) were prepared, namely the benzyl and octyl ester derivatives. Both benzyl and octyl ester monomers were oxidatively polymerized to yield dark, melanin‐like pigments. These polymerization processes were followed by UV–visible, fluorescence and NMR spectroscopy. These studies showed that the polymerizations proceeded by cross‐linking at the 4‐ and 7‐positions of the indole nucleus and led to highly heterogeneous polymeric products. Incorporation of a lipophilic benzyl or octyl group resulted in enhanced solubility of the pigments in a wide range of organic solvents. The UV–visible spectra of the organically soluble synthetic melanins were essentially identical to that of natural eumelanin.
• WO2007/91018
  申请人：——

  公开号：——

  公开（公告）日：——
• Marrel; Boss; Van De Waterbeemd, European Journal of Medicinal Chemistry, 1985, vol. 20, # 5, p. 459 - 465
  作者：Marrel、Boss、Van De Waterbeemd、et al.

  DOI：——

  日期：——
• EP1981839A1
  申请人：——

  公开号：EP1981839A1

  公开（公告）日：2008-10-22