(S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester | 928195-92-0

• 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: (S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester
• 英文别名: L-Tyrosine, 2,6-dimethyl-, methyl ester；methyl (2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoate
• CAS: 928195-92-0
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: LSDITFBEJIMPKY-NSHDSACASA-N

物化性质

• 沸点：
  366.8±37.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester 在 盐酸 、 氨 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 (S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanamide
  参考文献：
  名称：

  Studies on the structure–activity relationship of 2′,6′-dimethyl-l-tyrosine (Dmt) derivatives: bioactivity profile of H–Dmt–NH–CH3

  摘要：

  The 2',6'-dimethyl-L-tyrosine (Dmt) enhances receptor affinity, functional bioactivity and in vivo analgesia of opioid peptides. To further investigate its direct influence on these opioid parameters, we developed a series of compounds (H-Dmt-NH-X). Among them, H-Dmt-NH-CH3 showed the highest affinity (K(i)mu = 7.45 nM) equal to that of morphine, partial mu-opioid agonism (E-max = 66.6%) in vitro and a moderate antinociception in mice. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.040
• 作为产物：
  描述：

  甲醇 、 2',6'-二甲基-L-酪氨酸 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 生成 (S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionic acid methyl ester
  参考文献：
  名称：

  Studies on the structure–activity relationship of 2′,6′-dimethyl-l-tyrosine (Dmt) derivatives: bioactivity profile of H–Dmt–NH–CH3

  摘要：

  The 2',6'-dimethyl-L-tyrosine (Dmt) enhances receptor affinity, functional bioactivity and in vivo analgesia of opioid peptides. To further investigate its direct influence on these opioid parameters, we developed a series of compounds (H-Dmt-NH-X). Among them, H-Dmt-NH-CH3 showed the highest affinity (K(i)mu = 7.45 nM) equal to that of morphine, partial mu-opioid agonism (E-max = 66.6%) in vitro and a moderate antinociception in mice. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.040

文献信息

• US7439258B2
  申请人：——

  公开号：US7439258B2

  公开（公告）日：2008-10-21
• [EN] MULTIFUNCTIONAL OPIOID RECEPTOR LIGANDS AND METHODS OF TREATING PAIN<br/>[FR] LIGANDS MULTIFONCTIONNELS DU RÉCEPTEUR AUX OPIOÏDES ET PROCÉDÉS DE TRAITEMENT DE LA DOULEUR
  申请人：UNIV ARIZONA

  公开号：WO2016187537A1

  公开（公告）日：2016-11-24

  Opioid receptor ligands (ORLs) that are multifunciionai having agonist activity at mu opioid receptor (MOR), agonist activity at delta opioid receptor (DOR), and antagonist (or partial agonist) activity at kappa opioid receptor (KOR). The ORLs comprise peptide portions that are analogs derived from enkephalins, EM-1, or DALDA, as well as tail portions that comprise a lipophilic molecu!e such as a 4-anilidopiperidine moiety.
• [EN] SUBSTITUTED VICINAL DIAMINE COMPOUNDS AND THEIR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF PAIN<br/>[FR] COMPOSÉS DE DIAMINE VICINALE SUBSTITUÉS ET LEUR UTILISATION DANS LE TRAITEMENT, L'ATTÉNUATION OU LA PRÉVENTION DE LA DOULEUR
  申请人：UNIV FRIEDRICH ALEXANDER ER

  公开号：WO2022048922A1

  公开（公告）日：2022-03-10

  The present invention relates to a compound of the following formula (I) or (II), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, cocrystal, tautomer, racemate, enantiomer, or diastereomer or mixture thereof: The invention furthermore relates to a pharmaceutical composition comprising the compound having formula (I) or (II) and optionally one or more pharmaceutically acceptable excipient(s) and/or carrier(s), as well as to these compounds for use in the treatment, amelioration or prevention of pain, opioid overdose, addictions, neuropsychiatric disorders, Prader-Willi Syndrome, gastrointestinal disorders, skin disorders, dyspnea, headache and/or temporomandibular joint dysfunction, including methods of treating, ameliorating or preventing pain involving administering to a patient in need thereof an effective amount of the compound having formula (I) or (II).
• Studies on the structure–activity relationship of 2′,6′-dimethyl-l-tyrosine (Dmt) derivatives: bioactivity profile of H–Dmt–NH–CH3
  作者：Yoshio Fujita、Yuko Tsuda、Takashi Motoyama、Tingyou Li、Anna Miyazaki、Toshio Yokoi、Yusuke Sasaki、Akihiro Ambo、Hideko Niizuma、Yunden Jinsmaa、Sharon D. Bryant、Lawrence H. Lazarus、Yoshio Okada

  DOI：10.1016/j.bmcl.2004.11.040

  日期：2005.2

  The 2',6'-dimethyl-L-tyrosine (Dmt) enhances receptor affinity, functional bioactivity and in vivo analgesia of opioid peptides. To further investigate its direct influence on these opioid parameters, we developed a series of compounds (H-Dmt-NH-X). Among them, H-Dmt-NH-CH3 showed the highest affinity (K(i)mu = 7.45 nM) equal to that of morphine, partial mu-opioid agonism (E-max = 66.6%) in vitro and a moderate antinociception in mice. (C) 2004 Elsevier Ltd. All rights reserved.