(R)-(-)-2-(4-hydroxyphenyl)propanoic acid | 59092-88-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-(-)-2-(4-hydroxyphenyl)propanoic acid
• 英文别名: (R)-2-(4-hydroxyphenyl)propionic acid；2-(4-hydroxyphenyl)propionic acid；2-HPPA；(R)-(-)-2-(4-hydroxyphenyl)propionic acid；(2R)-2-(4-hydroxyphenyl)propanoic acid
• CAS: 59092-88-5
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: ZHMMPVANGNPCBW-ZCFIWIBFSA-N

物化性质

• 熔点：
  156-158 °C
• 沸点：
  328.3±17.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-(4-hydroxyphenyl)propanoic acid 在 盐酸 、 溶剂黄146 、 二异丙胺 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 41.5h， 生成 Meraxin
  参考文献：
  名称：

  Predicting Human Serum Albumin Affinity of Interleukin-8 (CXCL8) Inhibitors by 3D-QSPR Approach

  摘要：

  A novel class of 2-(R)-phenylpropionamides has been recently reported to inhibit in vitro and in vivo interleukin-8 (CXCL8)-induced biological activities, These CXCL8 inhibitors are derivatives of phenylpropionic nonsteroidal antiinflammatory drugs (NSAIDs), high-affinity ligands for site II of human serum albumin (HSA). Up to date, only a limited number of in silico models for the prediction of albumin protein binding are available. A three-dimensional quantitative structure-property relationship (3D-QSPR) approach was used to model the experimental affinity constant (K-i) to plasma proteins of 37 structurally related molecules, using physicochemical. and 3D-pharmacophoric descriptors. Molecular docking studies highlighted that training set molecules preferentially bind site II of HSA. The obtained model shows satisfactory statistical parameters both in fitting and predicting validation. External validation confirmed the statistical significance of the chemometric model, which is a powerful tool for the prediction of HSA binding in virtual libraries of structurally related compounds.

  DOI：

  10.1021/jm049227l
• 作为产物：
  描述：

  (R)-O-desmethylangolensin 在 碳酸氢钠 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 25.0h， 以0.5 mg的产率得到(R)-(-)-2-(4-hydroxyphenyl)propanoic acid
  参考文献：
  名称：

  立体化学法测定黄豆苷元生成的O-去甲基Angolensin

  摘要：

  我们已经分离出产生O-去甲基Angolensin（O- DMA）的细菌，梭状芽胞杆菌rRNA簇XIVa菌株SY8519。根据使用HPLC的手性分离，由SY8519产生的O -DMA表现出高的光学纯度。为了确定O -DMA的绝对立体化学，我们使用Baeyer-Villiger反应从O -DMA制备了2-（4-羟苯基）丙酸（2-HPPA）。从产物的手性分析，主峰具有与由染料木黄酮由相同细菌产生的2-HPPA相同的立体化学。由于我们已经确定SY8519生产2- HPPA的立体化学为具有ř结构，通过化学合成（小号）-2-HPPA，由SY8519生产的O -DMA在2位上还必须具有R立体化学。为了研究立体选择性代谢，我们将外消旋二氢黄豆苷元应用于SY8519。所述Ô -DMA从培养基中分离和也被回收的起始材料。所产生的O- DMA具有与黄豆苷元相似的光学活性。然而，剩余的二氢黄豆苷元在对映体之间没有

  DOI：

  10.1016/j.foodchem.2014.08.122

文献信息

• Lipase-catalyzed hydrolysis of 2-(4-hydroxyphenyl)propionic acid ethyl ester to (R)-(−)-2-(4-hydroxyphenyl)propanoic acid
  作者：Xin Yuan、Panliang Zhang、Guangyong Liu、Weifeng Xu、Kewen Tang

  DOI：10.1007/s11696-019-00796-9

  日期：2019.10

  Stereoselective hydrolysis of (±)-2-(4-hydroxyphenyl)propionic acid ethyl ester (2-HPPAEE) by lipase catalyzed in aqueous system was investigated. Lipase AK with higher catalytic activity and enantioselectivity was selected as catalyst. Simultaneously, factors affecting the conversion of substrate (c) and the enantiomeric excess of product (eep) were optimized. The optimal conditions were established

  研究了水体系中脂肪酶催化的（±）-2-（4-羟苯基）丙酸乙酯（2-HPPAEE）的立体选择性水解。选择具有较高催化活性和对映选择性的脂肪酶AK作为催化剂。同时，优化了影响底物（c）转化和产物的对映体过量（ee p）的因素。确定了最佳条件，包括温度45°C，pH 5.5，脂肪酶AK剂量10 mg，底物剂量0.04 mmol和反应时间40 h。在最佳条件下，c和ee p分别可达49％和98％。
• [EN] 2-ARYL-PROPIONIC ACIDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] ACIDES 2-ARYL-PROPIONIQUES ET COMPOSITIONS PHARMACEUTIQUES RENFERMANT CEUX-CI
  申请人：DOMPE SPA

  公开号：WO2003043625A1

  公开（公告）日：2003-05-30

  (R) and (S) 2-Aryl-propionic acids, and pharmaceutical compositions that contain them, are useful in inhibiting chemotactic activation of neutrophils (PMN leukocytes) induced by the interaction of Interleukin-8 (IL-8) with CXCR1 and CXCR2 membrane receptors. The acids are used for the prevention and treatment of pathologies deriving from said activation. In particular, the (R) enantiomers of said acids are lacking cyclo-oxygenase inhibition activity and are particularly useful in the treatment of neutrofil-dependent pathologies such as psoriasis, ulcerative colitis, melanoma, chronic obstructive pulmonary disease (COPD),bollous pemphigo, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of damages caused by ischemia and reperfusion.

  (R)和(S) 2-芳基丙酸及含有它们的药物组合物，可用于抑制由白细胞介素-8（IL-8）与CXCR1和CXCR2膜受体相互作用引起的嗜中性粒细胞（PMN白细胞）的趋化活化。这些酸用于预防和治疗由该活化引起的病理。特别地，这些酸的(R)对映体缺乏环氧合酶抑制活性，特别适用于治疗依赖于中性粒细胞的病理，如银屑病，溃疡性结肠炎，黑色素瘤，慢性阻塞性肺疾病（COPD），天疱疮，类风湿性关节炎，特发性纤维化，肾小球肾炎以及缺血再灌注所致的损伤的预防和治疗。
• 2-Aryl-propionic acids and pharmaceutical compositions containing them
  申请人：Allegretti Marcello

  公开号：US20050038119A1

  公开（公告）日：2005-02-17

  (R) and (S) 2-Aryl-propionic acids, and pharmaceutical compositions that contain them, are useful in inhibiting chemotactic activation of neutrophils (PMN leukocytes) induced by the interaction of Interleukin-8 (IL-8) with CXCR1 and CXCR2 membrane receptors. The acids are used for the prevention and treatment of pathologies deriving from said activation. In particular, the (R) enantiomers of said acids are lacking cyclo-oxygenase inhibition activity and are particularly useful in the tratment of neutrofil-dependent pathologies such as psoriasis, ulcerative colitis, melanoma, chronic obstructive pulmonary disease (COPD), bollous pemphigo, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of damages caused by ischemia and reperfusion.

  (R)和(S) 2-芳基-丙酸以及含有它们的制药组合物，在抑制由白细胞介素-8（IL-8）与CXCR1和CXCR2膜受体相互作用引起的嗜中性粒细胞（PMN白细胞）趋化激活方面非常有用。这些酸用于预防和治疗由该激活引起的病理状况。特别是，这些酸的(R)对映体缺乏环氧合酶抑制活性，特别适用于治疗依赖于嗜中性粒细胞的病理状况，如牛皮癣，溃疡性结肠炎，黑色素瘤，慢性阻塞性肺疾病（COPD），水疱性天疱疮，类风湿性关节炎，特发性纤维化，肾小球肾炎以及缺血再灌注所致的损伤的预防和治疗。
• Design, Synthesis, and Structure–Activity Relationship Studies of Novel GPR88 Agonists (4-Substituted-phenyl)acetamides Based on the Reversed Amide Scaffold
  作者：Md Toufiqur Rahman、Dongliang Guan、Hetti Handi Chaminda Lakmal、Ann M. Decker、Gregory H. Imler、Andrew T. Kerr、Danni L. Harris、Chunyang Jin

  DOI：10.1021/acschemneuro.3c00684

  日期：2024.1.3

  of GPR88 as a novel drug target for psychiatric and neurodegenerative disorders. Examination of structure–activity relationships of two known agonist scaffolds 2-PCCA and 2-AMPP, as well as the recently resolved cryo-EM structure of 2-PCCA-bound GPR88, led to the design of a new scaffold based on the “reversed amide” strategy of 2-AMPP. A series of novel (4-substituted-phenyl)acetamides were synthesized

  鉴于 GPR88 有望成为精神和神经退行性疾病的新型药物靶点，孤儿受体 GPR88 合成激动剂的开发最近引起了极大的兴趣。检查两种已知的激动剂支架 2-PCCA 和 2-AMPP 的构效关系，以及最近解析的 2-PCCA 结合的 GPR88 的冷冻电镜结构，导致基于 2-AMPP 的“反向酰胺”策略设计了一种新的支架。合成了一系列新型（4-取代-苯基）乙酰胺，并在 cAMP 积累测定中作为 GPR88 激动剂进行评估，这导致发现了几种与 2-AMPP 具有更好或相当效力的化合物。计算对接研究表明，这些新型 GPR88 激动剂与 2-PCCA 占据的 GPR88 变构位点结合。总的来说，我们的研究结果为 GPR88 变构位点的结构见解和 SAR 需求以及 GPR88 变构激动剂的进一步开发提供了新的支架。
• PROPIONIC ACID DERIVATIVE
  申请人：TEIKOKU CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0673924A1

  公开（公告）日：1995-09-27

  A propionic acid derivative represented by general formula (I) or a pharmaceutically acceptable acid-addition salt thereof, wherein A represents OH, C₁-C₈ lower alkoxy, -NR₁R₂, or C₁-C₈ lower alkoxy which may be substituted by halogen, optionally susbtituted aryl, -COB or succinimido; R₁ and R₂ represent each H, C₁-C₈ lower alkyl or optionally substituted aralkyl, or alternatively R₁ and R₂ are combined together with the adjacent nitrogen atoms to represent a heterocycle; and B represents OH, C₁-C₈ lower alkyl, optionally susbtituted aryl, optionally substituted aryloxy, C₁-C₈ lower alkoxy, optionally substituted aralkyloxy, or NR₁R₂ wherein R₁ and R₂ are each as defined above. This compound is useful as a protease inhibitor.

  通式 (I) 所代表的丙酸衍生物或其药学上可接受的酸加成盐，其中 A 代表 OH、C₁-C₈ 低级烷氧基、-NR₁R₂ 或可被卤素、任选取代的芳基、-COB 或琥珀酰亚胺取代的 C₁-C₈ 低级烷氧基；R₁ 和 R₂ 各自代表 H、C₁-C₈ 低级烷基或任选取代的芳基，或者 R₁ 和 R₂ 与相邻的氮原子结合在一起代表杂环；B 代表 OH、C₁-C₈ 低级烷基、任选取代的芳基、任选取代的芳氧基、C₁-C₈ 低级烷氧基、任选取代的芳氧基或 NR₁R₂，其中 R₁ 和 R₂ 各自如上定义。该化合物可用作蛋白酶抑制剂。