2-[4-(2-methylpropyl)phenyl]-N-(methylsulfonyl)propanamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-[4-(2-methylpropyl)phenyl]-N-(methylsulfonyl)propanamide
• 英文别名: reparixin；2-[4-(2-methylpropyl)phenyl]-N-methylsulfonylpropanamide
• 化学式: C₁₄H₂₁NO₃S
• 分子量: 283.392
• InChiKey: KQDRVXQXKZXMHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基磺酰胺 、 布洛芬 在 sodium hydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.0h， 以60%的产率得到2-[4-(2-methylpropyl)phenyl]-N-(methylsulfonyl)propanamide
  参考文献：
  名称：

  修饰的酸性非甾体抗炎药作为mPGES-1和5-LOX的双重抑制剂

  摘要：

  mPGES-1是开发新型抗炎药的有希望的目标。我们的目标是通过用磺酰胺部分取代羧酸官能团来修饰NSAIDs的结构来创建mPGES-1抑制剂。还测试了化合物对5-LOX的抑制作用。最有效的mPGES-1抑制剂是氯苯唑衍生物22（IC 50 = 0.16μM），而用吲哚美辛衍生物获得的最好的5-LOX的抑制17（IC 50 = 0.9微米）。完全消除了对COX-1活性的抑制。

  DOI：

  10.1021/jm3010543

文献信息

• A new and efficient method for the facile synthesis of N-acyl sulfonamides under Lewis acid catalysis
  作者：Chada Raji Reddy、Bodugam Mahipal、Srinivasa Rao Yaragorla

  DOI：10.1016/j.tetlet.2007.08.048

  日期：2007.10

  sulfonamides with carboxylic acid anhydrides in the presence of Lewis acids is described. Several Lewis acids such as BF3·Et2O, ZnCl2, MoCl5, TiCl4, B(C6F5)3, Sc(OTf)3 and I2 were found to catalyze the reaction efficiently to furnish the N-acylated products in good yields under solvent-free conditions. The reactions of various sulfonamides were studied with different carboxylic acid anhydrides including the

  描述了在路易斯酸存在下磺酰胺与羧酸酐的N-酰化。发现几种路易斯酸，例如BF 3 ·Et 2 O，ZnCl 2，MoCl 5，TiCl 4，B（C 6 F 5）3，Sc（OTf）3和I 2可以有效地催化反应以提供N-在无溶剂条件下，酰化产物的收率很高。在3 mol％ZnCl 2存在下，研究了各种磺酰胺与不同羧酸酐（包括反应性较低的苯甲酸酐和新戊酸酐）的反应作为催化剂。羧酸还通过混合酸酐法成功地用作酰化剂。
• 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。
• IL-8 INHIBITORS FOR USE IN THE TREATMENT OF CHEMOTHERAPY-INDUCED PERIPHERAL NEUROPATHY
  申请人：Dompé farmaceutici S.p.A.

  公开号：EP3192504A1

  公开（公告）日：2017-07-19

  The present invention relates to IL-8 inhibitor compounds, preferably dual CXCR1/CXCR2 receptor inhibitors, useful in the treatment and/or prevention of chemotherapy-induced peripheral neuropathy.

  本发明涉及IL-8抑制剂化合物，最好是CXCR1/CXCR2双重受体抑制剂，可用于治疗和/或预防化疗引起的周围神经病变。
• CXCL8 INHIBITORS FOR USE IN THE TREATMENT OF COVID-19
  申请人：Dompe' Farmaceutici S.P.A.

  公开号：EP3884932A1

  公开（公告）日：2021-09-29

  The present invention relates to CXCL8 inhibitors, such as reparixin, for use in the treatment of COVID-19 pneumonia.

  本发明涉及用于治疗 COVID-19 肺炎的 CXCL8 抑制剂，如 reparixin。
• Medical devices to prevent or inhibit restenosis
  申请人：Hezi-Yamit Ayala

  公开号：US20050261762A1

  公开（公告）日：2005-11-24

  Implantable medical devices having anti-restenotic coatings are disclosed. Specifically, implantable medical devices having coatings of certain anti-inflammatory agents, are disclosed. The-anti-inflammatory agents are selected from the group consisting of ENMD-0997, gusperimus hydrochloride, BMS-561392, CP-461, RDP-58, CNI-1493, CEP-1347, CMT-3, prinomastat, rebimastat, leflunomide, BX-471, DF-1681, BXT-51072, M-40403, LY-293111 sodium, and pharmaceutically acceptable derivatives thereof. The anti-restenotic medical devices include stents, catheters, micro-particles, probes and vascular grafts. Intravascular stents are preferred medical devices. The medical devices can be coated using any method known in the art including compounding the anti-inflammatory agent with a biocompatible polymer prior to applying the coating. Moreover, medical devices composed entirely of biocompatible polymer-anti-inflammatory agent blends are disclosed. Medical devices having a coating comprising at least one anti-inflammatory agent in combination with at least one additional therapeutic agent are also disclosed. Furthermore, related methods of using and making the anti-restenotic implantable devices are disclosed.

  本研究公开了具有抗血管狭窄涂层的植入式医疗器械。具体而言，本发明公开了具有某些抗炎剂涂层的植入式医疗器械。这些抗炎剂选自ENMD-0997、盐酸古培利莫、BMS-561392、CP-461、RDP-58、CNI-1493、CEP-1347、CMT-3、普利莫司他、瑞比莫司他、来氟米特、BX-471、DF-1681、BXT-51072、M-40403、LY-293111钠及其药学上可接受的衍生物组成的组。抗血管再狭窄医疗器械包括支架、导管、微颗粒、探针和血管移植物。血管内支架是首选的医疗器械。这些医疗器械可以使用本领域已知的任何方法进行涂布，包括在涂布前将消炎剂与生物相容性聚合物复合。此外，还公开了完全由生物相容性聚合物-消炎剂混合物组成的医疗器械。还公开了具有包含至少一种消炎剂和至少一种额外治疗剂的涂层的医疗器械。此外，还公开了使用和制造抗再狭窄植入装置的相关方法。