(R)-2-(4-hydroxyphenyl)propionic acid methyl ester | 533931-57-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-2-(4-hydroxyphenyl)propionic acid methyl ester
• 英文别名: Methyl (R)-2-(4-Hydroxyphenyl)propanoate；methyl (2R)-2-(4-hydroxyphenyl)propanoate
• CAS: 533931-57-6
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: QOHGMEYPUKSMST-SSDOTTSWSA-N

物化性质

• 沸点：
  272.0±15.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-(4-hydroxyphenyl)propionic acid methyl ester 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 23.5h， 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：

  甲醇 、 (R)-(-)-2-(4-hydroxyphenyl)propanoic acid 在 盐酸 作用下， 反应 18.0h， 以93%的产率得到(R)-2-(4-hydroxyphenyl)propionic acid methyl ester
  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

文献信息

• [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。
• 3-CARBAMOYL-2-PYRIDONE DERIVATIVE
  申请人：SHIONOGI & CO., LTD.

  公开号：EP1806342B1

  公开（公告）日：2013-04-17
• 2-ARYL-PROPIONIC ACIDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Dompé S.P.A.

  公开号：EP1455773A1

  公开（公告）日：2004-09-15
• US8063242B2
  申请人：——

  公开号：US8063242B2

  公开（公告）日：2011-11-22