1-[(S)-2-(3,4-dihydroxyphenyl)-1-methoxycarbonylethylcarbamoyl]-1-methyl-ethylammonium chloride | 946089-59-4

• 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: 1-[(S)-2-(3,4-dihydroxyphenyl)-1-methoxycarbonylethylcarbamoyl]-1-methyl-ethylammonium chloride
• 英文别名: methyl (2S)-2-[(2-amino-2-methylpropanoyl)amino]-3-(3,4-dihydroxyphenyl)propanoate;hydrochloride
• CAS: 946089-59-4
• 化学式: C₁₄H₂₀N₂O₅*ClH
• 分子量: 332.784
• InChiKey: OUAAHGVRFWQFMD-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.68
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  左旋多巴 在 盐酸 、 氯化亚砜 、 1-羟基苯并三唑 、 1,2-二氯乙烷 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[(S)-2-(3,4-dihydroxyphenyl)-1-methoxycarbonylethylcarbamoyl]-1-methyl-ethylammonium 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

文献信息

• Amino Acid Derivatives
  申请人：Hobbs Christopher

  公开号：US20090170937A1

  公开（公告）日：2009-07-02

  Compounds of formula (I) have activity in alleviating the effects of impaired dopaminergic signaling, for example in the treatment of Parkinsons Disease: wherein: R 1 is a carboxyl, carboxyl ester, or carboxamide group; R 2 and R 3 are independently hydrogen, or a group —C(═O)R 6 or —C(═O)OR 6 wherein Re is C 1 -C 6 alkyl, or a group —CH 2 Q wherein Q is an optionally substituted monocyclic carbocyclic or heterocyclyl ring of 3 to 6 ring atoms; R 4 and R 5 are independently (a) the side chain of a natural amino acid, or (b) optionally substituted C 1 -C 4 alkyl, C 2 -C 4 alkenyl, or C 2 -C 4 alkynyl, or (c) —CH 2 XCH 3 , —CH 2 CH 2 XCH 3 , or —CH 2 XCH 2 CH 3 , wherein X is —O—, S, or —NR 7 wherein R 7 is hydrogen, methyl or ethyl; or (d) —CH 2 Q or CH 2 OQ wherein Q is as defined in relation to R 6 ; or R 4 and R 5 taken together with the carbon atom to which they are attached form an optionally substituted cycloalkyl or heterocyclic ring of 3 to 8 ring atoms, optionally fused to a second, optionally substituted, carbocyclic or heterocyclic ring
• Design, synthesis and biological evaluation of peptide derivatives of l-dopa as anti-parkinsonian agents
  作者：Tao Zhou、Robert C. Hider、Peter Jenner、Bruce Campbell、Christopher J. Hobbs、Sarah Rose、Mark Jairaj、Kayhan A. Tayarani-Binazir、Alexander Syme

  DOI：10.1016/j.bmcl.2013.08.007

  日期：2013.10

  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.