3-ethoxy-4-[[(1S)-2,2,2-trifluoro-1-(4-propan-2-ylfuran-2-yl)ethyl]amino]cyclobut-3-ene-1,2-dione | 654683-14-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-ethoxy-4-[[(1S)-2,2,2-trifluoro-1-(4-propan-2-ylfuran-2-yl)ethyl]amino]cyclobut-3-ene-1,2-dione
• CAS: 654683-14-4
• 化学式: C₁₅H₁₆F₃NO₄
• 分子量: 331.292
• InChiKey: RPNOJIWVFXFFFZ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-氨基-2-羟基-N,N-二甲基苯甲酰胺 、 3-ethoxy-4-[[(1S)-2,2,2-trifluoro-1-(4-propan-2-ylfuran-2-yl)ethyl]amino]cyclobut-3-ene-1,2-dione 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 39.0h， 生成 (S)-3-(3,4-dioxo-2-(2,2,2-trifluoro-1-(4-isopropylfuran-2-yl)ethylamino)cyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamide
  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
• 作为产物：
  描述：

  4-Isopropyl-furan-2-carbonsaeure-methylester 在 盐酸 、 lithium aluminium tetrahydride 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 四氯化钛 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 54.5h， 生成 3-ethoxy-4-[[(1S)-2,2,2-trifluoro-1-(4-propan-2-ylfuran-2-yl)ethyl]amino]cyclobut-3-ene-1,2-dione
  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

• 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：Merck Sharp & Dohme Corp.

  公开号：EP1539678B1

  公开（公告）日：2012-09-05
• US7964646B2
  申请人：——

  公开号：US7964646B2

  公开（公告）日：2011-06-21