3-(4-chlorophenyl)-1-methyl-4-(4-sulfonamidophenyl)-1Hpyrrole-2,5-dione | 1599441-88-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-(4-chlorophenyl)-1-methyl-4-(4-sulfonamidophenyl)-1Hpyrrole-2,5-dione
• 英文别名: 3-(4-chlorophenyl)-4-(4-aminosulfonyl-phenyl)-1-methyl-1H-pyrrole-2,5-dione；MPO-0029；4-[4-(4-Chloro-phenyl)-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-benzenesulfonamide；4-[4-(4-chlorophenyl)-1-methyl-2,5-dioxopyrrol-3-yl]benzenesulfonamide
• CAS: 1599441-88-9
• 化学式: C₁₇H₁₃ClN₂O₄S
• 分子量: 376.82
• InChiKey: WKSXNSMQLGMRAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氯苯甲酰甲酸乙酯 在 水 、 乙酸酐 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 52.0h， 生成 3-(4-chlorophenyl)-1-methyl-4-(4-sulfonamidophenyl)-1Hpyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis, biological evaluation, and docking analysis of a novel family of 1-methyl-1H-pyrrole-2,5-diones as highly potent and selective cyclooxygenase-2 (COX-2) inhibitors

  摘要：

  As a continuous research for discovery of new COX-2 inhibitors, we present the simple chemical synthesis, in vitro biological screening, and molecular docking study of 1H-pyrrole-2,5-dione derivatives. New synthetic compounds were evaluated for the inhibitory activities on LPS-induced PGE(2) production in RAW 264.7 macrophage cells as well as the COX-1 and COX-2 inhibitory potency. Among them, compound 9d (MPO-0029) was identified as more potent and selective COX-2 inhibitor [PGE(2) IC50 = 8.7 nM, COX-2 IC50 = 6.0 nM; COX-2 selectivity index (SI) = > 168] than celecoxib. Molecular docking experiments were further performed against COX-2 and COX-1 isozymes to determine their probable binding models. Results of molecular docking studies revealed that compound 9d (MPO-0029) has stronger binding interaction with COX-2 than with COX-1 isozyme, and provided successfully complementary theoretical support for the obtained experimental biological data. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.074

文献信息

• PHARMACEUTICAL COMPOSITION FOR PREVENTION OR TREATMENT OF SPINAL CORD INJURY OR SPINAL STENOSIS
  申请人：NEUROBIT SCIENCE CO., LTD.

  公开号：US20220202774A1

  公开（公告）日：2022-06-30

  Proposed is a pharmaceutical composition for prevention or treatment of spinal cord injury or spinal stenosis. The pharmaceutical composition contains 3-(4-chlorophenyl)-4-(4-aminosulfonyl-phenyl)-1-methyl-1H-pyrrole-2,5-dione or a pharmaceutically acceptable salt thereof. It was newly discovered that the compound inhibits activities of pro-inflammatory cytokines and PGE 2 , which are inflammatory mediators, thereby suppressing inflammation or pain due to spinal cord injury or spinal stenosis. Since the compound can effectively inhibit inflammation or pain caused by spinal cord injury or spinal stenosis, it is expected that the compound will be useful for the prevention or treatment of spinal cord injury or spinal stenosis.
• [EN] PHARMACEUTICAL COMPOSITION FOR PREVENTION OR TREATMENT OF SPINAL CORD INJURY OR SPINAL STENOSIS<br/>[FR] COMPOSITION PHARMACEUTIQUE POUR LA PRÉVENTION OU LE TRAITEMENT D'UNE LÉSION DE LA MOELLE ÉPINIÈRE OU D'UNE STÉNOSE SPINALE<br/>[KO] 척수 손상 또는 척추관 협착증의 예방 또는 치료용 약제학적 조성물
  申请人：UNIV INDUSTRY COOPERATION GROUP KYUNG HEE UNIV

  公开号：WO2020209576A1

  公开（公告）日：2020-10-15

  본 발명은 3-(4-클로로페닐)-4-(4-아미노설폰일-페닐)-1-메틸-1H-피롤-2,5-디온 또는 이의 약제학적으로 허용되는 염을 포함하는 척수 손상 또는 척추관 협착증의 예방 또는 치료용 약제학적 조성물에 관한 것이다. 본 발명자들은 본 발명에 따른 화합물이 염증 매개 물질인 전염증성 사이토카인 및 PGE2을 억제해 척수 손상 또는 척추관 협착증의 염증 또는 통증을 억제하는 것을 새롭게 발견하였는바, 본 발명에 따른 화합물은 척수 손상 또는 척추관 협착증으로 인한 염증 또는 통증 등을 효과적으로 억제할 수 있어 상기 손상 또는 협착증의 예방 또는 치료가 이루어지는 데 유용하게 쓰일 것으로 기대된다.
• Synthesis, biological evaluation, and docking analysis of a novel family of 1-methyl-1H-pyrrole-2,5-diones as highly potent and selective cyclooxygenase-2 (COX-2) inhibitors
  作者：Kyung Ju Kim、Min Ji Choi、Ji-Sun Shin、Minju Kim、Hye-Eun Choi、Seoung Mook Kang、Jae Ho Jin、Kyung-Tae Lee、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2014.02.074

  日期：2014.4

  As a continuous research for discovery of new COX-2 inhibitors, we present the simple chemical synthesis, in vitro biological screening, and molecular docking study of 1H-pyrrole-2,5-dione derivatives. New synthetic compounds were evaluated for the inhibitory activities on LPS-induced PGE(2) production in RAW 264.7 macrophage cells as well as the COX-1 and COX-2 inhibitory potency. Among them, compound 9d (MPO-0029) was identified as more potent and selective COX-2 inhibitor [PGE(2) IC50 = 8.7 nM, COX-2 IC50 = 6.0 nM; COX-2 selectivity index (SI) = > 168] than celecoxib. Molecular docking experiments were further performed against COX-2 and COX-1 isozymes to determine their probable binding models. Results of molecular docking studies revealed that compound 9d (MPO-0029) has stronger binding interaction with COX-2 than with COX-1 isozyme, and provided successfully complementary theoretical support for the obtained experimental biological data. (c) 2014 Elsevier Ltd. All rights reserved.