(S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanamide | 331283-95-5

• 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-dimethylphenyl)propanamide
• 英文别名: H-Dmt-NH2；(2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanamide
• CAS: 331283-95-5
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: ALYWNQGYSGHOMA-JTQLQIEISA-N

物化性质

• 沸点：
  458.5±45.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  89.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanamide 在 硼烷四氢呋喃络合物 、 四丁基溴化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成
  参考文献：
  名称：

  SUBSTITUTED VICINAL DIAMINE COMPOUNDS AND THEIR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF PAIN

  摘要：

  本发明涉及以下式(I)或(II)的化合物，可选地以药物可接受的盐、溶剂化物、多晶形、共晶体、互变异构体、外消旋体、对映体或其混合物的形式存在：此外，本发明还涉及包含具有式(I)或(II)的化合物和可选地一种或多种药物可接受的辅料和/或载体的制药组合物，以及这些化合物用于治疗、改善或预防疼痛、阿片类药物过量、成瘾、神经精神障碍、普拉德-威利综合症、胃肠疾病、皮肤疾病、呼吸困难、头痛和/或颞下颌关节功能障碍的用途，包括通过向需要治疗的患者施用具有式(I)或(II)的化合物的有效量来治疗、改善或预防疼痛的方法。

  公开号：

  EP3964497A1
• 作为产物：
  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

文献信息

• Endomorphin analogues with balanced affinity for both μ- and δ-opioid receptors
  作者：Liang Zhang、Lei Chang、Lei Lei Yu、Jin Chun Liu、Jia Jia Chen、Xiao Wen Li、Lawrence H. Lazarus、Ting You Li

  DOI：10.1016/j.cclet.2011.01.035

  日期：2011.8

  Analogues of endomorphin and tripeptides modified at positions 4 and 3, respectively, with various phenylalanine analogues were synthesized and their affinities for opioid receptors were evaluated. Most of the peptides exhibited potent mu-receptor affinity and selectivity, among them, compound 7 (Dmt-Pro-Tmp-Tmp-NH2) exhibited potent affinity for both mu- and delta-receptors (K-i mu = 0.47 nmol/L, K-i delta = 1.63 nmol/L). (C) 2011 Ting You Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• MU OPIOID RECEPTOR MODULATORS
  申请人：The Regents of the University of California

  公开号：US20200109126A1

  公开（公告）日：2020-04-09

  Described herein, inter alia, are compositions and methods for modulating mu opioid receptor activity.
• 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.
• SUBSTITUTED VICINAL DIAMINE COMPOUNDS AND THEIR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF PAIN
  申请人：Friedrich-Alexander-Universität Erlangen-Nürnberg

  公开号：EP3964497A1

  公开（公告）日：2022-03-09

  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).

  本发明涉及以下式(I)或(II)的化合物，可选地以药物可接受的盐、溶剂化物、多晶形、共晶体、互变异构体、外消旋体、对映体或其混合物的形式存在：此外，本发明还涉及包含具有式(I)或(II)的化合物和可选地一种或多种药物可接受的辅料和/或载体的制药组合物，以及这些化合物用于治疗、改善或预防疼痛、阿片类药物过量、成瘾、神经精神障碍、普拉德-威利综合症、胃肠疾病、皮肤疾病、呼吸困难、头痛和/或颞下颌关节功能障碍的用途，包括通过向需要治疗的患者施用具有式(I)或(II)的化合物的有效量来治疗、改善或预防疼痛的方法。