1-(3-chloropropyl)-3-(4-(trifluoromethyl)phenyl)urea | 1422166-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-chloropropyl)-3-(4-(trifluoromethyl)phenyl)urea
• 英文别名: 1-(3-Chloropropyl)-3-[4-(trifluoromethyl)phenyl]urea；1-(3-chloropropyl)-3-[4-(trifluoromethyl)phenyl]urea
• CAS: 1422166-44-6
• 化学式: C₁₁H₁₂ClF₃N₂O
• 分子量: 280.677
• InChiKey: QQLNXSGYZNYFPV-UHFFFAOYSA-N

物化性质

• 沸点：
  325.3±42.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-chloropropyl)-3-(4-(trifluoromethyl)phenyl)urea 在 caesium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 1-[3-[4-[3-(Cyclohexylamino)-6-fluoroimidazo[1,2-a]pyridin-2-yl]-2-methoxyphenoxy]propyl]-3-[4-(trifluoromethyl)phenyl]urea
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship Studies of Novel Dual Inhibitors of Soluble Epoxide Hydrolase and 5-Lipoxygenase

  摘要：

  Current research leads to the assumption that drugs affecting more than one target could result in a more efficient treatment of diseases and fewer safety concerns. Administration of drugs inhibiting only one branch of the arachidonic acid cascade is usually accompanied by side effects. We therefore designed and synthesized a library of hybrid molecules incorporating an imidazo[1,2-a]pyridine and an urea moiety as novel soluble epoxide hydrolase (sEH)/5-lipoxygenase (5-LO) dual inhibitors. Evaluation of the compounds was accomplished by in vitro testing using recombinant enzyme assays.

  DOI：

  10.1021/jm301617j
• 作为产物：
  描述：

  3-氯丙基异氰酸酯 、 对三氟甲基苯胺 以 二氯甲烷 为溶剂， 生成 1-(3-chloropropyl)-3-(4-(trifluoromethyl)phenyl)urea
  参考文献：
  名称：

  磺酰脲类NLRP3炎性体抑制剂的设计，合成和筛选

  摘要：

  炎性小体是多蛋白装配体，当用病原体和/或危险相关的分子模式刺激时，会产生强烈的炎症反应。不受控制的炎性体激活与多种疾病的病理生理有关，包括威胁生命的病原体感染，例如弗朗西斯菌。小分子炎症小体抑制剂的开发引起了人们的极大兴趣。使用基于查尔酮衍生物的计算模型，我们开发了新型的叔磺酰脲类化合物作为NLRP3炎性体的抑制剂。查尔酮的极性烯酮功能警戒剂被磺酰脲类支架取代，同时保持两个芳环的相对位置。评价了这些化合物抑制由土拉弗朗西斯菌感染触发的NLRP3和AIM2炎症小体活化的能力。

  DOI：

  10.1007/s00044-019-02466-7

文献信息

• [EN] NADPH OXIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE LA NADPH OXYDASE ET LEUR UTILISATION
  申请人：UNIV EMORY

  公开号：WO2019023448A1

  公开（公告）日：2019-01-31

  This disclosure relates to compounds and methods of treating or preventing a Nox related disease or condition comprising administering to a subject in need thereof a Nox inhibitor or pharmaceutical compositions comprising a Nox inhibitor disclosed herein, derivatives, or compounds disclosed herein optionally substituted with one or more substitutes including optional salt and prodrug forms. In certain embodiments, this disclosure relates to sulfonylurea compounds and uses reported herein.

  本公开涉及化合物和治疗或预防与Nox相关的疾病或症状的方法，包括向需要的受试者施用本公开披露的Nox抑制剂或含有本公开披露的Nox抑制剂、衍生物或化合物的药物组合物，该药物组合物可选择地用一个或多个替代物替代，包括可选的盐和前药形式。在某些实施例中，本公开涉及磺酰脲化合物和此处报告的用途。
• NADPH oxidase inhibitors and uses thereof
  申请人：Emory University

  公开号：US11236053B2

  公开（公告）日：2022-02-01

  This disclosure relates to compounds and methods of treating or preventing a Nox related disease or condition comprising administering to a subject in need thereof a Nox inhibitor or pharmaceutical compositions comprising a Nox inhibitor disclosed herein, derivatives, or compounds disclosed herein optionally substituted with one or more substitutes including optional salt and prodrug forms. In certain embodiments, this disclosure relates to sulfonylurea compounds and uses reported herein.

  本公开涉及治疗或预防与Nox相关的疾病或病症的化合物和方法，包括向有需要的受试者施用Nox抑制剂或药物组合物，其中包含本文公开的Nox抑制剂、衍生物或本文公开的化合物，可任选被一种或多种替代物取代，包括任选的盐和原药形式。在某些实施方案中，本公开涉及本文所报道的磺酰脲化合物及其用途。
• Design, synthesis, and biological evaluation of inhibitors of the NADPH oxidase, Nox4
  作者：Qian Xu、Amol A. Kulkarni、Ayyiliath M. Sajith、Dilbi Hussein、David Brown、Osman F. Güner、M. Damoder Reddy、E. Blake Watkins、Bernard Lassègue、Kathy K. Griendling、J. Phillip Bowen

  DOI：10.1016/j.bmc.2017.12.023

  日期：2018.3

  NADPH oxidases (Nox enzymes) are critical mediators of both physiologic and pathophysiologic processes. Nox enzymes catalyze NADPH-dependent generation of reactive oxygen species (ROS), including superoxide and hydrogen peroxide. Until recently, Nox4 was proposed to be involved exclusively in normal physiologic functions. Compelling evidence, however, suggests that Nox4 plays a critical role in fibrosis, as well as a host of pathologies and diseases. These considerations led to a search for novel, small molecule inhibitors of this important enzyme. Ultimately, a series of novel tertiary sulfonylureas (23-25) was designed using pharmacophore modeling, synthesized, and evaluated for inhibition of Nox4-dependent signaling. (C) 2017 Elsevier Ltd. All rights reserved.
• NADPH Oxidase Inhibitors and Uses Thereof
  申请人：Emory University

  公开号：US20200270214A1

  公开（公告）日：2020-08-27

  This disclosure relates to compounds and methods of treating or preventing a Nox related disease or condition comprising administering to a subject in need thereof a Nox inhibitor or pharmaceutical compositions comprising a Nox inhibitor disclosed herein, derivatives, or compounds disclosed herein optionally substituted with one or more substitutes including optional salt and prodrug forms. In certain embodiments, this disclosure relates to sulfonylurea compounds and uses reported herein.
• Design, synthesis, and screening of sulfonylurea-derived NLRP3 inflammasome inhibitors
  作者：Amol A. Kulkarni、Ayyiliath M. Sajith、Trevor T. Duarte、Anahis Tena、Charles T. Spencer、J. Phillip Bowen

  DOI：10.1007/s00044-019-02466-7

  日期：2020.1

  development of small molecule inflammasome inhibitors. Using computational modeling based on chalcone derivatives, we have developed novel tertiary sulfonylurea compounds as inhibitors of the NLRP3 inflammasome. The polar enone functional alert of chalcone was replaced with a sulfonylurea scaffold while maintaining the relative positions of the two aromatic rings. These compounds were evaluated for their

  炎性小体是多蛋白装配体，当用病原体和/或危险相关的分子模式刺激时，会产生强烈的炎症反应。不受控制的炎性体激活与多种疾病的病理生理有关，包括威胁生命的病原体感染，例如弗朗西斯菌。小分子炎症小体抑制剂的开发引起了人们的极大兴趣。使用基于查尔酮衍生物的计算模型，我们开发了新型的叔磺酰脲类化合物作为NLRP3炎性体的抑制剂。查尔酮的极性烯酮功能警戒剂被磺酰脲类支架取代，同时保持两个芳环的相对位置。评价了这些化合物抑制由土拉弗朗西斯菌感染触发的NLRP3和AIM2炎症小体活化的能力。