3-[[3-[(二甲氨基)羰基]-2-羟基苯基]氨基]-4-[[(R)-1-(4-异丙基呋喃-2-基)丙基]氨基]环丁-3-烯-1,2-二酮 | 473728-58-4

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-[[3-[(二甲氨基)羰基]-2-羟基苯基]氨基]-4-[[(R)-1-(4-异丙基呋喃-2-基)丙基]氨基]环丁-3-烯-1,2-二酮
• 中文别名: 3-[[3-[(二甲氨基)羰基]-2-羟苯基]氨基]-4-[[(R)-1-(4-异丙呋喃-2-基)丙基]氨基]环丁基-3-烯-1,2-二酮
• 英文名称: SCH563705
• 英文别名: (R)-2-Hydroxy-3-((2-((1-(4-isopropylfuran-2-yl)propyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)-N,N-dimethylbenzamide；3-[[3,4-dioxo-2-[[(1R)-1-(4-propan-2-ylfuran-2-yl)propyl]amino]cyclobuten-1-yl]amino]-2-hydroxy-N,N-dimethylbenzamide
• CAS: 473728-58-4
• 化学式: C₂₃H₂₇N₃O₅
• 分子量: 425.484
• InChiKey: DGKQQEVYYPCMNE-OAHLLOKOSA-N

物化性质

• 沸点：
  555.9±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• 储存条件：
  2-8℃

制备方法与用途

SCH 563705 是一种有效的可口服的 CXCR2 和 CXCR1 拮抗剂，其 IC50 值分别为 1.3 nM 和 7.3 nM，Ki 值分别为 1 nM 和 3 nM。

反应信息

• 作为产物：
  描述：

  3-硝基水杨酸 在 palladium on activated charcoal 草酰氯 、 氢气 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-[[3-[(二甲氨基)羰基]-2-羟基苯基]氨基]-4-[[(R)-1-(4-异丙基呋喃-2-基)丙基]氨基]环丁-3-烯-1,2-二酮
  参考文献：
  名称：

  C(4)-alkyl substituted furanyl cyclobutenediones as potent, orally bioavailable CXCR2 and CXCR1 receptor antagonists

  摘要：

  A novel series of cyclobutenedione centered C(4)-alkyl substituted furanyl analogs was developed as potent CXCR2 and CXCR1 antagonists. Compound 16 exhibits potent inhibitory activities against IL-8 binding to the receptors (CXCR2 Ki = 1 nM, IC50 = 1.3 nM; CXCRI Ki = 3 nM, IC50= 7.3 nM), and demonstrates potent inhibition against both Gro-alpha and IL-8 induced hPMN migration (chemotaxis: CXCR2 IC50=0.5nM,CXCRI IC50= 37 nN1). In addition, 16 has shown good oral pharmacokinetic profiles in rat, mouse, monkey, and dog. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.016

文献信息

• Treatment of chemokine mediated diseases
  申请人：Taveras G. Arthur

  公开号：US20070155756A1

  公开（公告）日：2007-07-05

  Methods of treating chemokine-mediated diseases are disclosed. The methods comprise the administration of CXC-Chemokine receptor antagonists of the formula or pharmaceutically acceptable salts or solvates thereof, in combination with other classes of pharmaceutical compounds. The chemokine-mediated diseases include acute and chronic inflammatory disorders, psoriasis, cystic fibrosis, asthma and cancer. Also disclosed are novel compounds of formula (I).

  本发明揭示了治疗趋化因子介导疾病的方法。该方法包括给予以下公式的CXC趋化因子受体拮抗剂或其药学上可接受的盐或溶剂，与其他类别的药物化合物结合使用。趋化因子介导的疾病包括急性和慢性炎症性疾病、银屑病、囊性纤维化、哮喘和癌症。本发明还揭示了公式（I）的新化合物。
• 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
  申请人：Taveras G. Arthur

  公开号：US20070021494A1

  公开（公告）日：2007-01-25

  There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

  公开了以下化合物的公式或其药学上可接受的盐或溶剂，它们可用于治疗趋化因子介导的疾病，如急性和慢性炎症性疾病和癌症。
• 3,4-DI-SUBSTITUTED CYCLOBUTENE-1,2-DIONES AS CXC-CHEMOKINE RECEPTOR LIGANDS
  申请人：Taveras Arthur G.

  公开号：US20090306079A1

  公开（公告）日：2009-12-10

  There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

  公开了以下式子的化合物，或其药学上可接受的盐或溶剂，其对于化学因子介导的疾病如急慢性炎症性疾病和癌症的治疗是有用的。
• 3,4-Di-Substituted Cyclobutene-1,2-Diones as CXC-Chemokine Receptor Ligands
  申请人：Taveras Arthur G.

  公开号：US20110213029A1

  公开（公告）日：2011-09-01

  There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

  公开了以下式的化合物，或其药学上可接受的盐或溶剂，它们可用于治疗由趋化因子介导的疾病，如急性和慢性炎症性疾病和癌症。
• 3,4-DI-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
  申请人：SCHERING CORPORATION

  公开号：EP1818325A2

  公开（公告）日：2007-08-15

  There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

  已公开的化合物式如下 或其药学上可接受的盐或溶液，可用于治疗由趋化因子介导的疾病，如急性和慢性炎症性疾病和癌症。