O-甲基-L-酪氨酸盐酸盐 | 67423-44-3

• 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: O-甲基-L-酪氨酸盐酸盐
• 英文名称: O-methyl-L-tyrosine hydrochloride
• 英文别名: (2S)-2-amino-3-(4-methoxyphenyl)propanoic acid;hydrochloride
• CAS: 67423-44-3
• 化学式: C₁₀H₁₃NO₃*ClH
• mdl: MFCD00058082
• 分子量: 231.679
• InChiKey: OWJANEXICRZDJT-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.34
• 重原子数：
  15
• 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：
  72.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  O-甲基-L-酪氨酸盐酸盐 在 盐酸 、 Dowex 1XB 、 氨 、 lithium 、 碳酸氢钠 作用下， 生成 methyl (2S,3aS,7aS)-1-benzyl-6-oxo-octahydroindole-2-carboxylate
  参考文献：
  名称：

  Synthesis of the octahydroindole core of aeruginosins: a new bicyclic α-amino acid

  摘要：

  The first synthesis of 6-hydroxyoctahydroindole-2-carboxylic acid derivatives with a cis fusion in the azabicyclic nucleus is described. The synthesis involves a Birch reduction of O-methyl-L-tyrosine followed by an aminocyclization in acid medium to give a mixture of 6-oxo-octahydroindole-2-carboxylic acids 3 and 4, which could be separated after dibenzylation. Transesterification, hydrogenolysis in the presence of acetic anhydride and reduction of the amido ketones 9 and 10 provides the four stereoisomeric alcohols from which alcohol 14 showed nmr data very close to the aeruginosin 298-A core. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00225-x
• 作为产物：
  描述：

  O-methyl-tyrosine methyl ester; hydrochloride 在 Aspergillus niger lipase 、 sodium acetate buffer 作用下， 生成 O-甲基-L-酪氨酸盐酸盐 、 O-甲基-D-酪氨酸盐酸盐
  参考文献：
  名称：

  Empirical rules for the enantiopreference of lipase from Aspergillus niger toward secondary alcohols and carboxylic acids, especially α-amino acids

  摘要：

  Lipase from Aspergillus niger (ANL, Amano lipase AP) catalyzes enantioselective hydrolysis and acylation reactions. To aid in the design of new applications of this lipase, we propose two empirical rules that predict which enantiomer reacts faster. For secondary alcohols, a rule proposed previously for other lipases also works for ANL, but with lower reliability (77%, 37 of 48 examples). For carboxylic acids, we examined both crude and partially-purified ANL because commercial ANL contains contaminating hydrolases. Partial purification removed a contaminating amidase and increased the enantioselectivity of ANL toward many alpha-amino acids, including cyclic amino acids. Unlike other lipases, ANL readily accepts positively-charged substrates and shows the highest enantioselectivity toward alpha-amino acids. Although a rule based on the sizes of the substituents could not predict the fast-reacting enantiomer, a rule limited to alpha-amino acids did predict the fast-reacting enantiomer. We estimate that the charged alpha-amino group contributes a factor of 40-100 (Delta Delta G double dagger=2.2-2.7 kcal/mol) to the enantioselectivity of ANL towards carboxylic acids. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00524-7

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AS HIV PROTEASE INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES EN TANT QU'INHIBITEURS DE LA PROTÉASE DU VIH
  申请人：MERCK SHARP & DOHME

  公开号：WO2018106519A1

  公开（公告）日：2018-06-14

  The present invention is directed to compounds of Formula (I), pharmaceutical compositions comprising the same, and their use in the inhibition of HIV protease, the inhibition of HIV replication, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS.

  本发明涉及式(I)的化合物，包括相同的药物组合物，以及它们在抑制HIV蛋白酶、抑制HIV复制、预防HIV感染、治疗HIV感染以及预防、治疗和延缓艾滋病的发病或进展中的用途。
• One-Pot Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Aldehydes and Amines
  作者：Juan Xie、Stéphane Maisonneuve

  DOI：10.1055/s-0029-1218267

  日期：2009.11

  A one-pot, three-step synthesis of 1,4-disubstituted 1,2,3-triazoles from aldehyde and amine has been developed by in situ transformation of aldehyde into alkyne, followed by diazo- transfer of amine into azide and subsequent cycloaddition. This pro- cedure allowed the synthesis of fluorescent amino acid derivatives as well as glycoconjugate mimetics.

  通过将醛原位转化为炔烃，然后将胺重氮转移为叠氮化物并随后进行环加成，已开发出一种由醛和胺合成 1,4-二取代 1,2,3-三唑的一锅三步法. 该程序允许合成荧光氨基酸衍生物以及糖缀合物模拟物。
• First Total Syntheses of Aeruginosin 298-A and Aeruginosin 298-B, Based on a Stereocontrolled Route to the New Amino Acid 6-Hydroxyoctahydroindole-2-carboxylic Acid
  作者：Nativitat Valls、Meritxell López-Canet、Mercè Vallribera、Josep Bonjoch

  DOI：10.1002/1521-3765(20010817)7:16<3446::aid-chem3446>3.0.co;2-0

  日期：2001.8.17

  The first total syntheses of aeruginosin 298-A (1) and aeruginosin 298-B (3) are described. The syntheses of the alternative putative structures 2 and 4 were also accomplished. The key common strategic element is the stereo-controlled synthesis of (2S,3aS,6R,7aS)-6-hydroxyoctahydroindole-2-carboxylic acid (L-Choi, 5) from L-tyrosine. The synthesis of this new bicyclic alpha-amino acid, which is the core

  描述了铜绿素298-A（1）和铜绿素298-B（3）的第一批合成。还完成了备选推定结构2和4的合成。关键的共同战略要素是从L-酪氨酸立体控制合成（2S，3aS，6R，7aS）-6-羟基八氢吲哚-2-羧酸（L-Choi，5）。作为铜绿素酶的核心，这种新的双环α-氨基酸的合成涉及桦木还原O-甲基-L-酪氨酸（6）和在酸性介质中将所得的二氢茴香醚7进行氨基环化，然后进行N-苄基化，得到非对映异构体12和13。用HCl-MeOH酸处理后，最后两个产生平衡混合物，其中内异构体13明显占优势。在（Boc）2O存在下加氢13得到16，经LS-Selectride还原后，可提供醇22（一种受保护的L-Choi）。22与D-亮氨酸，受保护的（R）-（4-羟苯基）乳酸和L-精氨酸片段的连续偶联，然后降低至精氨酸水平和脱保护的最终步骤完成了合成序列，产生了铜绿素酶298-A （1）。光谱比较显示，肽2具有先前针
• [EN] HETEROCYCLIC DERIVATIVES AND THEIR USE AS ANTITHROMBOTIC AGENTS<br/>[FR] DERIVES HETEROCYCLIQUES ET LEUR UTILISATION EN TANT QU'AGENTS ANTITHROMBOTIQUES
  申请人：AKZO NOBEL N.V.

  公开号：WO1998047876A1

  公开（公告）日：1998-10-29

  (EN) The present invention relates to antithrombotic compounds comprising the group Q, Q having formula (I), wherein the substructure (i) is a structure selected from (a, b and c), wherein X is O or S; X' being independently CH or N; and m is 0, 1, 2 or 3; wherein the group Q is bound through an oxygen atom or an optionally substituted nitrogen or carbon atom, or a pharmaceutically acceptable salt thereof or a prodrug thereof. The compounds of the invention are therapeutically active and in particular are antithrombotic agents.(FR) La présente invention concerne des composé antithrombotiques comprenant le groupe Q correspondant à la formule (I) dans laquelle la sous-structure (i) est une structure choisie parmi (a), (b) ou (c) où X représente O ou S, X' représente indépendamment CH ou N, et m vaut 0, 1, 2 ou 3, le groupe Q étant fixé au moyen d'un atome d'oxygène ou d'un atome de carbone ou d'azote éventuellement substitué. L'invention concerne également un sel ou un promédicament de ces composés, acceptable sur le plan pharmacologique. Les compositions de l'invention sont actives sur le plan thérapeutique et constituent notamment des agents antithrombotiques.

  该发明涉及抗血栓化合物，包括具有公式（I）的Q基团，其中亚结构（i）是从（a）、（b）和（c）中选择的结构，其中X为O或S；X'独立地为CH或N；m为0、1、2或3；其中Q基团通过氧原子或可选择的取代氮或碳原子结合，或其药学可接受的盐或前药。该发明的化合物具有治疗活性，特别是抗血栓剂。
• Heterocyclic derivatives and their use as antithrombotic agents
  申请人：——

  公开号：US20030130270A1

  公开（公告）日：2003-07-10

  The present invention relates to antithrombotic compounds comprising the group Q, Q having formula (I), wherein the substructure (i) is a structure selected from (a, b and c), wherein X is 0 or S; X′ being independently CH or N; and m is 0, 1, 2 or 3; wherein the group Q is bound through an oxygen atom or an optionally substituted nitrogen or carbon atom, or a pharmaceutically acceptable salt thereof or a prodrug thereof. The compounds of the invention are therapeutically active and in particular are antithrombotic agents. 1

  本发明涉及抗血栓化合物，包括具有公式（I）的Q基团，其中亚结构（i）是从（a、b和c）中选择的结构，其中X为0或S；X'独立地为CH或N；m为0、1、2或3；其中Q基团通过氧原子或可选择取代的氮或碳原子结合，或其药学上可接受的盐或前药。本发明的化合物具有治疗活性，特别是抗血栓剂。