N-[(R)-2-(3-cyclopentanecarbonylphenyl)propionyl]methanesulfonamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(R)-2-(3-cyclopentanecarbonylphenyl)propionyl]methanesulfonamide
• 英文别名: (2R)-2-[3-(cyclopentanecarbonyl)phenyl]-N-methylsulfonylpropanamide
• 化学式: C₁₆H₂₁NO₄S
• 分子量: 323.413
• InChiKey: ALVSFWLWMDNFCI-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲基磺酰胺 在 N,N'-羰基二咪唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 17.5h， 以79%的产率得到N-[(R)-2-(3-cyclopentanecarbonylphenyl)propionyl]methanesulfonamide
  参考文献：
  名称：

  WO2006/63999

  摘要：

  公开号：

文献信息

• 2-Arylpropionic Acid Derivatives and Pharmaceutical Compositions Containing Them
  申请人：Allegretti Marcello

  公开号：US20080312293A1

  公开（公告）日：2008-12-18

  The present invention relates to selected (R)-2-phenyl-propionamides and (R)-2-phenyl-sulfonamides with a hydrogen bond acceptor atom/group in a well defined position in the chemical space. These compounds show a surprising potent inhibitory effect on C5a induced human PMN chemotaxis. The compounds of the invention absolutely lack of CXCL8 inhibitory activity. Said compounds are useful in the treatment of pathologies depending on the chemotactic activation of neutrophils and monocytes induced by the fraction C5a of the complement. In particular, the compounds of the invention are useful in the treatment of sepsis, psoriasis, rheumatoid arthritis, ulcerative colitis, acute respiratory distress syndrome, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of injury caused by ischemia and reperfusion.

  本发明涉及在化学空间中具有氢键受体原子/基团的选定（R）-2-苯基-丙酰胺和（R）-2-苯基-磺酰胺。这些化合物表现出惊人的强烈抑制C5a诱导的人类PMN趋化性的效果。本发明的化合物绝对缺乏CXCL8抑制活性。所述化合物在治疗与补体C5a诱导的中性粒细胞和单核细胞趋化活化有关的病理过程中有用。特别是，在治疗败血症、牛皮癣、类风湿性关节炎、溃疡性结肠炎、急性呼吸窘迫综合征、特发性纤维化、肾小球肾炎以及缺血再灌注损伤的预防和治疗方面，本发明的化合物非常有用。
• 2-arylpropionic acid derivatives and pharmaceutical compositions containing them
  申请人：DompePHA.R.MA S.p.A.

  公开号：US07939521B2

  公开（公告）日：2011-05-10

  The present invention relates to selected (R)-2-phenyl-propionamides and (R)-2-phenyl-sulfonamides with a hydrogen bond acceptor atom/group in a well defined position in the chemical space. These compounds show a surprising potent inhibitory effect on C5a induced human PMN chemotaxis. The compounds of the invention absolutely lack of CXCL8 inhibitory activity. Said compounds are useful in the treatment of pathologies depending on the chemotactic activation of neutrophils and monocytes induced by the fraction C5a of the complement. In particular, the compounds of the invention are useful in the treatment of sepsis, psoriasis, rheumatoid arthritis, ulcerative colitis, acute respiratory distress syndrome, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of injury caused by ischemia and reperfusion.

  本发明涉及在化学空间中特定位置具有氢键受体原子/基团的选择性(R)-2-苯基-丙酰胺和(R)-2-苯基-磺酰胺。这些化合物表现出对C5a诱导的人类PMN趋化的惊人的强效抑制作用。本发明的化合物绝对不具有CXCL8抑制活性。该化合物在治疗依赖于补体C5a诱导的中性粒细胞和单核细胞趋化活化的病理过程中非常有用。特别是，本发明的化合物在治疗败血症、银屑病、类风湿性关节炎、溃疡性结肠炎、急性呼吸窘迫综合症、特发性纤维化、肾小球肾炎以及缺血再灌注引起的损伤的预防和治疗中非常有用。
• 2-ARYLPROPIONIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：DOMPE' pha.r.ma S.p.A.

  公开号：EP1856031A1

  公开（公告）日：2007-11-21
• US7939521B2
  申请人：——

  公开号：US7939521B2

  公开（公告）日：2011-05-10
• [EN] 2-ARYLPROPIONIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] DÉRIVÉS DE L'ACIDE 2-ARYLPROPIONIQUE ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CEUX-CI
  申请人：DOMPE SPA

  公开号：WO2006063999A1

  公开（公告）日：2006-06-22

  [EN] The present invention relates to selected (R)-2-phenyl-propionamides and (R)-2-phenyl-sulfonamides with a hydrogen bond acceptor atom/group in a well defined position in the chemical space. These compounds show a surprising potent inhibitory effect on C5a induced human PMN chemotaxis. The compounds of the invention absolutely lack of CXCL8 inhibitory activity. Said compounds are useful in the treatment of pathologies depending on the chemotactic activation of neutrophils and monocytes induced by the fraction C5a of the complement. In particular, the compounds of the invention are useful in the treatment of sepsis, psoriasis, rheumatoid arthritis, ulcerative colitis, acute respiratory distress syndrome, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of injury caused by ischemia and reperfusion.
  [FR] La présente invention concerne des (R)-2-phénylpropionamides et des (R)-2-phénylsulfonamides ayant un atome/groupe accepteur de liaison hydrogène en une position bien définie dans l'espace chimique. Ces composés présentent un effet inhibiteur puissant étonnant sur la chimiotaxie des PMN humains induite par le C5a. Les composés de l'invention n'ont absolument aucune activité d'inhibition de la CXCL8. Lesdits composés sont utiles dans le traitement de pathologies dépendantes de l'activation chimiotactique de neutrophiles et de monocytes induite par la fraction C5a du complément. En particulier, les composés de l'invention sont utiles dans le traitement de la sepsie, du psoriasis, de la polyarthrite rhumatoïde, de la recto-colite hémorragique, du syndrome de détresse respiratoire aiguë, de la fibrose idiopathique, de la glomérulonéphrite et dans la prévention et le traitement d'une plaie provoquée par l'ischémie et la reperfusion.