(S)-2,6-二甲基酪氨酸甲酯盐酸盐 | 928138-99-2

• 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: (S)-2,6-二甲基酪氨酸甲酯盐酸盐
• 英文名称: methyl (S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoate hydrochoride
• 英文别名: (S)-methyl 2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoate hydrochloride；methyl (2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoate;hydrochloride
• CAS: 928138-99-2
• 化学式: C₁₂H₁₇NO₃*ClH
• 分子量: 259.733
• InChiKey: KJIXJNWQADIOQQ-MERQFXBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  17
• 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：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2,6-二甲基酪氨酸甲酯盐酸盐 在 sodium carbonate 、 氨 作用下， 以 水 、 甲醇 为溶剂， 反应 168.0h， 以97%的产率得到(S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanamide
  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：

  甲醇 、 2',6'-二甲基-L-酪氨酸 在 氯化亚砜 作用下， 生成 (S)-2,6-二甲基酪氨酸甲酯盐酸盐
  参考文献：
  名称：

  Transformation of μ-opioid receptor agonists into biologically potent μ-opioid receptor antagonists

  摘要：

  N-Allylation (-CH2-CH=CH2) of [Dmt(1)]endomorphins yielded the following: (i) [N-allyl-Dmt(1)]endomorphin-2 (Dmt = 2',6'-dimethyl-L-tyrosine) (12) and [N-allyl-Dmt(1)]endomorphin-1 (15) (K-i mu = 0.45 and 0.26 nM, respectively) became p-antagonists (pA(2) = 8.59 and 8.18, respectively) with weak delta-antagonism (pA(2) = 6.32 and 7.32, respectively); (ii) intracerebroventricularly administered 12 inhibited morphine-induced CNS-mediated antinociception in mice [AD(50) (0.148 ng/mouse) was 16-fold more potent than naloxone], but not spinal antinociception, and (iii) 15 reversed the alcohol-elevated frequency in spontaneous inhibitory post-synaptic currents (IPSC) in hippocampal CA1 pyramidal cells in rat brain slices (P = 0.0055). Similarly, N-allylation of the potent mu-opioidmimetic agonists, 1,6-bis-[H-Dmt-NH]-hexane and 3,6-bis-[Dmt-NH-propyl]-2(1H)-pyrazinone, converted them into p-antagonists (pA(2) = 7.23 and 7.17 for the N-allyl-derivatives 17 and 19, respectively), and exhibited weak delta-antagonism. Thus, N-allylation of Dmt containing opioid peptides or opioidmimetics; continues to provide a facile means to convert selective mu-opioid agonists into potent mu-opioid antagonists. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.019

文献信息

• Viral polymerase inhibitors
  申请人：——

  公开号：US20020065418A1

  公开（公告）日：2002-05-30

  A compound of the formula I: 1 wherein: X is CH or N; Y is O or S; Z is OH, NH 2 , NMeR 3 , NHR 3 ; OR 3 or 5- or 6-membered heterocycle, having 1 to 4 heteroatoms selected from 0, N and S, said heterocycle being optionally substituted with from 1 to 4 substituents; A is N, COR 7 or CR 5 , wherein R 5 is H, halogen, or (C 1-6 ) alkyl and R 7 is H or (C 1-6 alkyl), with the proviso that X and A are not both N; R 6 is H, halogen, (C 1-6 alkyl) or OR 7 , wherein R 7 is H or (C 1-6 alkyl); R 1 is selected from the group consisting of 5- or 6-membered heterocycle having 1 to 4 heteroatoms selected from O, N, and S, phenyl, phenyl(C 1-3 )alkyl, (C 2-6 )alkenyl, phenyl(C 2-6 )alkenyl, (C 3-6 )cycloalkyl, (C 1-6 )alkyl, CF 3 , 9- or 10-membered heterobicycle having 1 to 4 heteroatoms selected from O, N and S, wherein said heterocycle, phenyl, phenyl(C 2-6 )alkenyl and phenyl(C 1-3 )alkyl), alkenyl, cycloalkyl, (C 1-6 )alkyl, and heterobicycle are all optionally substituted with from 1 to 4 substituents R 2 is selected from (C 1-6 )alkyl, (C 3-7 )cycloalkyl, (C 3-7 )cycloalkyl(C 1-3 )alkyl, (C 6-10 )bicycloalkyl, adamantyl, phenyl, and pyridyl, all of which is optionally substituted with from1 to 4 substituents; R 3 is selected from H, (C 1-6 )alkyl, (C 3-6 )cycloalkyl, (C 3 6 )cycloalkyl(C 1-6 )alkyl, (C 6-10 )aryl, (C 6-10 )aryl(C 1-6 )alkyl, (C 2-6 )alkenyl, (C 3-6 )cycloalkyl(C 2-6 )alkenyl, (C 6-10 )aryl(C 2-6 )alkenyl, N{(C 1-6 )alkyl} 2 , NHCOO(C 1-6 )alkyl(C 6-10 )aryl, NHCO(C 6-10 )aryl, (C 1-6 )alkyl-5- or 10-atom heterocycle, having 1 to 4 heteroatoms selected from O, N and S, and 5- or 10-atom heterocycle having 1 to 4 heteroatoms selected from O, N and S; wherein said alkyl, cycloalkyl, aryl, alkenyl and heterocycle are all optionally substituted with from 1 to 4 substituents; n is zero or 1; or a detectable derivative or salt thereof. The compounds of the invention may be used as inhibitors of hepatitis C virus replication. The invention further provides a method for treating or preventing hepatitis C virus infection.

  该化合物的结构式为I:1，其中：X为CH或N；Y为O或S；Z为OH、NH2、NMeR3、NHR3、OR3或含有1至4个异原子（0、N和S）的5-或6-成员杂环，该杂环可选择性地与1至4个取代基取代；A为N、COR7或CR5，其中R5为H、卤素或（C1-6）烷基，R7为H或（C1-6）烷基，但X和A不能同时为N；R6为H、卤素、（C1-6）烷基或OR7，其中R7为H或（C1-6）烷基；R1选自包括含有1至4个异原子（O、N和S）的5-或6-成员杂环、苯基、苯基（C1-3）烷基、（C2-6）烯基、苯基（C2-6）烯基、（C3-6）环烷基、（C1-6）烷基、CF3、含有1至4个异原子（O、N和S）的9-或10-成员杂环的群体，其中该杂环、苯基、苯基（C2-6）烯基和苯基（C1-3）烷基、烯基、环烷基、（C1-6）烷基和杂环均可选择性地与1至4个取代基取代；R2选自（C1-6）烷基、（C3-7）环烷基、（C3-7）环烷基（C1-3）烷基、（C6-10）双环烷基、金刚烷基、苯基和吡啶基，所有这些基均可选择性地与1至4个取代基取代；R3选自H、（C1-6）烷基、（C3-6）环烷基、（C3-6）环烷基（C1-6）烷基、（C6-10）芳基、（C6-10）芳基（C1-6）烷基、（C2-6）烯基、（C3-6）环烷基（C2-6）烯基、（C6-10）芳基（C2-6）烯基、N(C1-6)烷基2、NHCOO(C1-6)烷基（C6-10）芳基、NHCO（C6-10）芳基、（C1-6）烷基-含有1至4个异原子（O、N和S）的5-或10-原子杂环和含有1至4个异原子（O、N和S）的5-或10-原子杂环；其中所述烷基、环烷基、芳基、烯基和杂环均可选择性地与1至4个取代基取代；n为零或1；或其可检测衍生物或盐。该发明的化合物可用作乙型肝炎病毒复制的抑制剂。该发明还提供了一种治疗或预防乙型肝炎病毒感染的方法。
• Convenient, asymmetric synthesis of enantiomerically pure 2′,6′-dimethyltyrosine (DMT) via alkylation of chiral equivalent of nucleophilic glycine
  作者：Xuejun Tang、Vadim A. Soloshonok、Victor J. Hruby

  DOI：10.1016/s0957-4166(00)00250-0

  日期：2000.7

  Asymmetric synthesis of (S)-2′,6′-dimethyltyrosine (DMT) via reactions of 4′-benzyloxy-2′,6′-dimethylbenzyl bromide with Ni(II)-complexes of the chiral Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone was developed. Inexpensive and readily available reagents and solvents involved, including recyclable chiral auxiliary, simplicity of the experimental procedures and high chemical

  通过4'-苄氧基-2'，6'-二甲基苄基溴与甘氨酸手性席夫碱的Ni（II）络合物与（S）的反应，不对称合成（S）-2'，6'-二甲基酪氨酸（DMT）） - ø - [ ñ - （ñ -benzylprolyl）氨基]苯甲酮被开发。所涉及的廉价且容易获得的试剂和溶剂，包括可回收的手性助剂，简单的实验程序和高化学产率，使得该方法对于以克为单位制备目标氨基酸具有合成吸引力。
• Exploring the biological consequences of conformational changes in aspartame models containing constrained analogues of phenylalanine
  作者：Adriano Mollica、Sako Mirzaie、Roberto Costante、Simone Carradori、Giorgia Macedonio、Azzurra Stefanucci、Szabolcs Dvoracsko、Ettore Novellino

  DOI：10.3109/14756366.2015.1076811

  日期：2016.11.1

  The dipeptide aspartame (Asp-Phe-OMe) is a sweetener widely used in replacement of sucrose by food industry. 2 ',6 '-Dimethyltyrosine (DMT) and 2 ',6 '-dimethylphenylalanine (DMP) are two synthetic phenylalanine-constrained analogues, with a limited freedom in chi-space due to the presence of methyl groups in position 2 ',6 ' of the aromatic ring. These residues have shown to increase the activity of opioid peptides, such as endomorphins improving the binding to the opioid receptors. In this work, DMT and DMP have been synthesized following a diketopiperazine-mediated route and the corresponding aspartame derivatives (Asp-DMT-OMe and Asp-DMP-OMe) have been evaluated in vivo and in silico for their activity as synthetic sweeteners.
• VIRAL POLYMERASE INHIBITORS
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD.

  公开号：EP1301487A2

  公开（公告）日：2003-04-16
• US6448281B1
  申请人：——

  公开号：US6448281B1

  公开（公告）日：2002-09-10