(R)-2-[4-[(三氟甲基磺酰基)氧基]苯基]丙酸 | 533931-60-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: (R)-2-[4-[(三氟甲基磺酰基)氧基]苯基]丙酸
• 英文名称: (R)-2-(4-trifluoromethanesulfonyloxyphenyl)propionic acid
• 英文别名: (2R)-2-[(4-trifluoromethanesulfonyloxy)phenyl]propanoic acid；(R)-2-[4-[[(trifluoromethyl)sulfonyl]oxy]phenyl]propanoic Acid；(2R)-2-[4-(trifluoromethylsulfonyloxy)phenyl]propanoic acid
• CAS: 533931-60-1
• 化学式: C₁₀H₉F₃O₅S
• 分子量: 298.24
• InChiKey: NHVNEQGTEVFGPL-ZCFIWIBFSA-N

物化性质

• 熔点：
  57-60 °C
• 沸点：
  374.2±42.0 °C(Predicted)
• 密度：
  1.525±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 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：
  89
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-2-[4-[(三氟甲基磺酰基)氧基]苯基]丙酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 [4-[(2R)-1-(methoxyamino)-1-oxopropan-2-yl]phenyl] trifluoromethanesulfonate
  参考文献：
  名称：

  设计对CXCR1和CXCR2起作用的非竞争性白介素8抑制剂。

  摘要：

  趋化因子CXCL8和CXCL1在炎症部位中性粒细胞募集中起关键作用。CXCL8结合两个膜受体CXCR1和CXCR2，而CXCL1是CXCR2的选择性激动剂。在过去的十年中，已经研究了CXCL8和CXCL1的生理病理学作用。已鉴定出一类新型的小分子量变构CXCR1抑制剂，第一个候选药物reparixin目前正在临床研究中，以预防器官移植中的缺血/再灌注损伤。研究了Reparixin与CXCR1的结合模式，并将其用于双变构CXCR1和CXCR2抑制剂的计算机辅助设计程序。本文讨论了由模型驱动的SAR研究用于鉴定有效双重抑制剂的结果，并提出了三种新化合物（56、67，

  DOI：

  10.1021/jm061469t
• 作为产物：
  描述：

  (R)-2-(4-hydroxyphenyl)propionic acid methyl ester 在 盐酸 、 溶剂黄146 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (R)-2-[4-[(三氟甲基磺酰基)氧基]苯基]丙酸
  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

• 2-phenylpropionic acid derivatives and pharmaceutical compositions containing them
  申请人：——

  公开号：US08039656B2

  公开（公告）日：2011-10-18

  4-(trifluoromethanesulfonyloxyphenyl)propionic acid derivatives and pharmaceutical composition containing such compounds are useful in inhibiting the chemotactic activation of neutrophils (PMN leukocytes) induced by the interaction of Interleukin-8 (IL-8) with CXCR1 and CXCR2 membrane receptors. The compounds are used for the prevention and treatment of pathologies deriving from said activation. Notably, these metabolites are devoid of cyclo-oxygenase inhibition activity and are particularly useful in the treatment of neutrophil-dependent pathologies such as psoriasis, ulcerative colitis, melanoma, chronic obstructive pulmonary disease (COPD), bullous pemphigoid, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of damages caused by ischemia and reperfusion.

  4-(三氟甲磺酰氧基苯基)丙酸衍生物及含有此类化合物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中性粒细胞（PMN白细胞）趋化活化。这些化合物用于预防和治疗由该活化引起的病理情况。值得注意的是，这些代谢物不具有环氧化酶抑制活性，特别适用于治疗中性粒细胞依赖性病理情况，例如银屑病、溃疡性结肠炎、黑色素瘤、慢性阻塞性肺病（COPD）、大疱性类天疱疮、类风湿性关节炎、特发性纤维化、肾小球肾炎以及预防和治疗缺血再灌注引起的损伤。
• 2-aryl-propionic acids and pharmaceutical compositions containing them
  申请人：Dompe PHA.R.MA S.p.A.

  公开号：US08063242B2

  公开（公告）日：2011-11-22

  (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-芳基丙酸以及含有它们的制药组合物，对于抑制由Interleukin-8 (IL-8)与CXCR1和CXCR2膜受体相互作用引起的中性粒细胞（PMN白细胞）趋化激活非常有用。这些酸被用于预防和治疗由该激活引起的病理。特别是，这些酸的(R)对映体缺乏环氧化酶抑制活性，特别适用于治疗依赖于中性粒细胞的病理，例如银屑病、溃疡性结肠炎、黑色素瘤、慢性阻塞性肺疾病（COPD）、大疱性天疱疮、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引起的损害的预防和治疗。
• [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。
• WO2007/60215
  申请人：——

  公开号：——

  公开（公告）日：——