3-(3,4-dihydroxy-phenyl)-3-hydroxy-2-methylamino-propionic acid | 89754-21-2

• 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
• 英文名称: 3-(3,4-dihydroxy-phenyl)-3-hydroxy-2-methylamino-propionic acid
• 英文别名: 3-(3,4-Dihydroxy-phenyl)-3-hydroxy-2-methylamino-propionsaeure；N-methyl-L-threo-3-(3,4-dihydroxyphenyl)serine；3-(3,4-Dihydroxyphenyl)-3-hydroxy-2-(methylamino)propanoic acid
• CAS: 89754-21-2；89754-26-7；92843-36-2；92843-37-3；96554-46-0；110013-50-8；110013-51-9
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.217
• InChiKey: RPXZFIAFSLMEJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-bis(ethoxycarboxy)-benzaldehyde 在 乙醚 、 2-(甲基氨基)乙酸乙酯 、 sodium 、 溶剂黄146 作用下， 生成 3-(3,4-dihydroxy-phenyl)-3-hydroxy-2-methylamino-propionic acid
  参考文献：
  名称：

  Dalgliesh; Mann, Journal of the Chemical Society, 1947, p. 661

  摘要：

  DOI：

文献信息

• Threo-adrenalinecarboxylic acid, processes for the production thereof, and pharmaceutical compositions thereof
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0112606A1

  公开（公告）日：1984-07-04

  DL- and L-Threo-3-(3,4-dihydroxyphenyl)-N-methyl-serine which may also be termed as DL- and L-threo-adrenalinecarboxylic acid are now provided, which are new compounds useful for therapeutic treatment of Parkinson's disease and mental depression disease. DL-Adrenalinecarboxylic acid may be produced by a new process comprising reacting glycine with O-protected 3,4-dihydroxybenzaldehyde, hydrolyzing the resultant reaction product under acidic conditions to form O-protected DL-3-(3,4-dihydroxyphenyl)serine, isolating the O-protected DL-3-(3,4-dihydroxyphenyl)serine into the threo isomer and the erythro isomer by recrystallization from a suitable organic solvent, introducing an unsubstituted or substituted benzyl group into the 2-amino group of the resulting O-protected DL-threo-3-(3,4-dihydroxyphenyl)serine, then N-methylating the resulting O-protected DL-threo-3-(3,4-dihydroxyphenyl)-N-benzylserine,and removing the O-protecting groups as well as the unsubstituted or substituted benzyl group at the 2-methylamino group of the N-methylation product. L-threo-Adrenalinecarboxylic acid may be produced by a new process comprising introducing a p-methoxybenzyloxycarbonyl group into the 2-amino group of the O-protected DL-threo-3-(3,4-dihydroxyphenyl)serine obtained as an intermediate product, optically resolving the resultant 0-protected DL-threo-3-(3,4-dihydroxyphenyl)-N-p-methoxybenzyloxycarbonyl-serine by reacting the latter with an optically active amine and recrystallizing the resultant amine salt products from a suitable organic solvent, removing the p-methoxybenzyloxycarbonyl group from the resultant O-protected L-threo-(3,4-dihydroxyphenyl)-N-p-methoxybenzyloxycarbonyl-serine, reacting the resultant O-protected L-threo-(3,4-dihydroxyphenyl)serine with dimethyl sulfate in dry acetone to form an O-protected L-threo-(3,4-dihydroxyphenyl)-N-methylserine methyl ester, saponifying this methyl ester and then removing the O-protecting groups from the saponification product.

  现在提供的 DL-和 L-苏-3-(3,4-二羟基苯基)-N-甲基丝氨酸也可称为 DL-和 L-苏-肾上腺素羧酸，它们是可用于治疗帕金森病和精神抑郁症的新化合物。DL-肾上腺素羧酸可通过一种新工艺生产，该工艺包括使甘氨酸与 O-保护的 3,4-二羟基苯甲醛反应，在酸性条件下水解反应产物，形成 O-保护的 DL-3-(3,4-二羟基苯基)丝氨酸，通过从合适的有机溶剂中重结晶，将 O-保护的 DL-3-(3,4-二羟基苯基)丝氨酸分离成苏氨酸异构体和赤藓醇异构体、将未取代或取代的苄基引入到所得 O-保护的 DL-苏-3-(3,4-二羟基苯基)丝氨酸的 2-氨基中，然后将所得 O-保护的 DL-苏-3-(3,4-二羟基苯基)-N-苄丝氨酸 N-甲基化，并去除 O-保护基团以及 N-甲基化产物的 2-甲基氨基上的未取代或取代的苄基。 L-硫代肾上腺素羧酸可通过一种新工艺生产，该工艺包括在作为中间产物获得的 O-保护基 DL-硫代-3-(3,4-二羟基苯基)丝氨酸的 2-氨基上引入对甲氧基苄氧羰基、通过使 0-保护的 DL-苏氨酰-3-(3,4-二羟基苯基)-N-对甲氧基苄氧羰基丝氨酸与光学活性胺反应，并从合适的有机溶剂中重结晶所得到的胺盐产物，从而对 0-保护的 DL-苏氨酰-3-(3,4-二羟基苯基)-N-对甲氧基苄氧羰基丝氨酸进行光学解析、从得到的 O-保护的 L-硫代-(3,4-二羟基苯基)-N-对甲氧基苄氧羰基丝氨酸中除去对甲氧基苄氧羰基，将得到的 O-保护的 L-硫代-(3、在干丙酮中与硫酸二甲酯反应，形成 O-保护的 L-硫代-(3,4-二羟基苯基)-N-甲基丝氨酸甲酯，将该甲酯皂化，然后从皂化产物中去除 O-保护基团。
• A process for producing an optically active 3-(3,4-dihydroxphenyl) serine and a proteced derivative thereof
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0141613A2

  公开（公告）日：1985-05-15

  N-acyl-DL-3-(3,4-dihydroxyphenyl)serine or a catecholic hydroxyl-protected derivative thereof is stereospecifically de-acylated by reaction with a microorganism of Streptomyces or Streptoverticillium having an acylase or with an extract of said microorganism containing said acylase, to produce L-3-(3,4-dihydroxyphenyl)serine or the hydroxyl-protected derivative thereof, with the N-acyl-D-3-(3,4-dihydroxyphenyl)serine compound remaining unaltered. The L-3-(3,4-dihydroxyphenyl)-serine compound so produced can be separated from the N-acyl-D-3-(3,4-dihydroxyphenyl)serine compound owing to its different properties.

  将 N-酰基-DL-3-(3,4-二羟基苯基)丝氨酸或其羟基保护的儿茶酚衍生物与具有酰化酶的链霉菌或链孢霉微生物或含有所述酰化酶的所述微生物提取物反应，进行立体定向脱酰化、生成 L-3-(3,4-二羟基苯基)丝氨酸或其羟基保护衍生物，而 N-酰基-D-3-(3,4-二羟基苯基)丝氨酸化合物保持不变。由于 N-酰基-D-3-(3,4-二羟基苯基)丝氨酸化合物具有不同的性质，因此可以将这样制得的 L-3-(3,4-二羟基苯基)丝氨酸化合物与 N-酰基-D-3-(3,4-二羟基苯基)丝氨酸化合物分开。
• N-Methylphenylserine alkyl ester derivatives and uses thereof
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0218440A2

  公开（公告）日：1987-04-15

  As new compounds N-methyl-3-(3,4-dihydroxyphenyl)serine alkyl esters. These are effective as a-adrenergic and β-adrenergic agenta to stimulate the a-adrenergic and β-adrenergic functions of the central nervous system of mammalian animals. Such compounds can be useful for therapeutic treatment of disorders as invoked by reduced biological activities or functions of the a-and/or β-adrenergic neurons. N-methyl-L-threo-3-(3,4-dihydroxyphenyl)serine (C1 - Cs) alkyl esters are preferred amongst the new compounds of this invention.

  作为新化合物的 N-甲基-3-（3,4-二羟基苯基）丝氨酸烷基酯。这些化合物作为 a-肾上腺素能和β-肾上腺素能制剂，可有效刺激哺乳动物中枢神经系统的 a-肾上腺素能和β-肾上腺素能功能。此类化合物可用于治疗因 a 和/或 β 肾上腺素能神经元的生物活性或功能降低而引起的疾病。在本发明的新化合物中，N-甲基-L-苏-3-(3,4-二羟基苯基)丝氨酸(C1-Cs)烷基酯是首选。
• Cyclic peptide derivative, method for preparing same and composition thereof
  申请人：NATIONAL UNIVERSITY CORPORATION, IWATE UNIVERSITY

  公开号：US10654890B2

  公开（公告）日：2020-05-19

  Provided is a cyclic peptide derivative which is derived from Paecilomyces tenuipes having an astrocyte proliferative activity, or a salt thereof.

  本文提供了一种从具有星形胶质细胞增殖活性的栉水母菌（Paecilomyces tenuipes）中提取的环肽衍生物或其盐。
• UMEHDZAVA, XAMAO;NAGATSU, TOSIXARU;NARAXAYASI, XIROTARO;TAKEHUTI, TOMIO;I+
  作者：UMEHDZAVA, XAMAO、NAGATSU, TOSIXARU、NARAXAYASI, XIROTARO、TAKEHUTI, TOMIO、I+

  DOI：——

  日期：——