BETA-氨基-4-羟基苯丙醇盐酸盐 | 40829-04-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 氨基醇类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: BETA-氨基-4-羟基苯丙醇盐酸盐
• 中文别名: (R)-beta-氨基-4-羟基苯丙醇盐酸盐；(R)-Β-氨基-4-羟基苯丙醇盐酸盐；D-酪氨醇盐酸盐；D-酪氨醇 盐酸盐
• 英文名称: (R)-tyrosinol hydrochloride
• 英文别名: D-tyrosinol hydrochloride；4-[(2R)-2-amino-3-hydroxypropyl]phenol;hydrochloride
• CAS: 40829-04-7
• 化学式: C₉H₁₃NO₂*ClH
• 分子量: 203.669
• InChiKey: PNGCRFWYSRUQTB-DDWIOCJRSA-N

物化性质

• 熔点：
  167 °C
• 比旋光度：
  15 º (C=1, H2O 22 ºC)

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.5
• 氢给体数：
  4
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2922509090
• 危险品运输编号：
  2735
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  BETA-氨基-4-羟基苯丙醇盐酸盐 在 吡啶 、 copper diacetate 、 三溴化硼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 (R)-4-(4-(2-amino-3-hydroxypropyl)-2,6-diiodophenoxy)phenol
  参考文献：
  名称：

  [EN] SUBSTITUTED 4-PHENOXYPHENOL ANALOGS AS MODULATORS OF PROLIFERATING CELL NUCLEAR ANTIGEN ACTIVITY
  [FR] ANALOGUES DE 4-PHÉNOXYPHÉNOL SUBSTITUÉS EN TANT QUE MODULATEURS DE L'ACTIVITÉ DE L'ANTIGÈNE NUCLÉAIRE DE PROLIFÉRATION CELLULAIRE

  摘要：

  公开号：

  WO2013006734A8
• 作为产物：
  描述：

  (+/-)-2-amino-3-(4-hydroxy-phenyl)-propan-1-ol; hydrochloride 在 chiral stationary phase including isopropyl-functionalized CF₆ 作用下， 以 甲醇 、 溶剂黄146 、 三乙胺 、 乙腈 为溶剂， 生成 L-酪氨醇盐酸盐 、 BETA-氨基-4-羟基苯丙醇盐酸盐
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS
  [FR] COMPOSITIONS ET PROCÉDÉS POUR DES CYCLOFRUCTANES EN TANT QU'AGENTS DE SÉPARATION

  摘要：

  公开号：

  WO2010148191A3

文献信息

• Functionally Optimized Neuritogenic Farinosone C Analogs: SAR-Study and Investigations on Their Mode of Action
  作者：Patrick Burch、Andrea Chicca、Jürg Gertsch、Karl Gademann

  DOI：10.1021/ml400435h

  日期：2014.2.13

  products derived from entomopathogenic fungi have been shown to initiate neuronal differentiation in the rat pheochromocytoma PC12 cell line. After the successful completion of the total synthesis program, the reduction of structural complexity while retaining biological activity was targeted. In this study, farinosone C served as a lead structure and inspired the preparation of small molecules with reduced

  几种源自昆虫病原真菌的天然产物已显示在大鼠嗜铬细胞瘤 PC12 细胞系中启动神经元分化。在成功完成全合成程序后，目标是在保持生物活性的同时降低结构复杂性。在这项研究中，法里松酮 C 作为先导结构并启发了复杂性降低的小分子的制备，其中一些能够诱导神经突生长。这允许详细说明结构-活性关系。利用计算相似性集成方法对作用模式的研究表明，内源性大麻素系统作为我们类似物的潜在靶标的参与，还导致发现了四种有效的新内源性大麻素转运抑制剂。
• The anandamide membrane transporter. Structure–activity relationships of anandamide and oleoylethanolamine analogs with phenyl rings in the polar head group region
  作者：Vincenzo Di Marzo、Alessia Ligresti、Enrico Morera、Marianna Nalli、Giorgio Ortar

  DOI：10.1016/j.bmc.2004.07.026

  日期：2004.10

  A new series of anandamide and N-oleoylethanolamine analogs, most of which with aromatic moieties in the head group region, has been synthesized and evaluated as inhibitors of anandamide uptake. Some of them efficaciously inhibit the uptake process with K-i values in the low micromolar range (2.4-21.2 muM). Strict structural requisites are needed to observe a significant inhibition and in no case inhibition of fatty acid amidohydrolase overlaps with inhibition of anandamide uptake. (C) 2004 Elsevier Ltd. All rights reserved.
• Novel selective and metabolically stable inhibitors of anandamide cellular uptake
  作者：Giorgio Ortar、Alessia Ligresti、Luciano De Petrocellis、Enrico Morera、Vincenzo Di Marzo

  DOI：10.1016/s0006-2952(03)00109-6

  日期：2003.5

  Novel aromatic analogues of N-oleoylethanolamine and N-arachidonoylethanolamine (anandamide, AEA) were synthesized and, based on the capability of similar compounds to interact with proteins of the endocannabinoid and endovanilloid signaling systems, were tested on: (i) cannabinoid CB1 and CB2 receptors; (ii) vanilloid VR1 receptors; (iii) anandamide cellular uptake (ACU); and (iv) the fatty acid amide hydrolase (FAAH). The (R)- and, particularly, the (S)-1'-(4-hydroxybenzyl) derivatives of N-oleoylethanolamine and AEA (OMDM-1, OMDM-2, OMDM-3, and OMDM-4) inhibited to a varied extent ACU in RBL-2H3 cells (K-i ranging between 2.4 and 17.7 muM), the oleoyl analogues (OMDM-1 and OMDM-2, K-i 2.4 and 3.0 muM, respectively) being 6- to 7-fold more potent than the arachidonoyl analogues (OMDM-3 and OMDM-4). These four compounds exhibited: (i) poor affinity for either CB1 (K(i)greater than or equal tomuM) or CB2 (K-i>10 muM) receptors in rat brain and spleen membranes, respectively; (ii) almost no activity at vanilloid receptors in the intracellular calcium assay carried out with intact cells over-expressing the human VR1 (EC(50)greater than or equal to10 muM); and (iii) no activity as inhibitors of FAAH in N18TG2 cell membranes (K-i>50 muM). The oleoyl- and arachidonoyl-N'-(4-hydroxy-3-methoxybenzyl)hydrazines (OMDM-5 and OMDM-6), inhibited ACU (K-i 4.8 and 7.0 muM, respectively), and were more potent as VR1 agonists (EC50 75 and 50 nM, respectively), weakly active as CB1 receptor ligands (K-i 4.9 and 3.2 muM, respectively), and inactive as CB2 ligands (K-i>5 muM) as well as on FAAH (K(i)greater than or equal to40 muM). In conclusion, we report two novel potent and selective inhibitors of ACU (OMDM-1 and OMDM-2) and one "hybrid" agonist of CB1 and VR1 receptors (OMDM-6). Unlike other compounds of the same type, OMDM-1, OMDM-2, and OMDM-6 were very stable to enzymatic hydrolysis by rat brain homogenates. (C) 2003 Elsevier Science Inc. All rights reserved.
• Total Synthesis and Neuritotrophic Activity of Farinosone C and Derivatives
  作者：Henning J. Jessen、Damien Barbaras、Matthias Hamburger、Karl Gademann

  DOI：10.1021/ol901277q

  日期：2009.8.6

  An efficient synthesis of all four possible stereoisomers of the neurotrophic amide farinosone C was developed. The absolute and relative configuration was assigned by comparison of synthetic material with a derivatized authentic sample of the natural product. Several derivatives allowed for the generation of preliminary structure activity relationships concerning neurite outgrowth in PC-12 cells, unravelling L-tyrosinol-amide as the pharmacophore.