1-[5-(3-amino-phenoxy)-pentyl]-3-naphthalen-1-yl-thiourea | 1092450-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[5-(3-amino-phenoxy)-pentyl]-3-naphthalen-1-yl-thiourea
• 英文别名: 1-[5-(3-Aminophenoxy)pentyl]-3-naphthalen-1-ylthiourea；1-[5-(3-aminophenoxy)pentyl]-3-naphthalen-1-ylthiourea
• CAS: 1092450-84-4
• 化学式: C₂₂H₂₅N₃OS
• 分子量: 379.526
• InChiKey: JDPLFRMSRAYZKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[5-(3-amino-phenoxy)-pentyl]-3-naphthalen-1-yl-thiourea 在 氨 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 1-(naphthalen-1-yl)-3-[5-(3-thioureidophenoxy)pentyl]thiourea
  参考文献：
  名称：

  Modulation of microglial immune responses by a novel thiourea derivative

  摘要：

  Increasing evidence indicates that microglial activation plays an important role in the pathogenesis of Alzheimer's disease (AD). In AD, activated microglia may facilitate the clearance of beta-amyloid (A beta), a neurotoxic component in AD pathogenesis. However, microglial activation comes at the cost of triggering neuro-inflammation, which contributes to cerebral dysfunction. Thus, pharmacological approaches that can achieve a favorable combination of a reduced microglia-mediated neuro-inflammation, and an enhanced A beta clearance may be beneficial for preventing the progression of the disease. Here, we show that some newly synthesized compounds may exert such a combination of functions. Using mouse primary microglia and RAW264.7 cells, we found that some thiourea derivatives significantly enhanced microglial A beta phagocytosis and suppressed microglial immune responses, as evidenced by the reduced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2). Of note, some commercially available inhibitors for iNOS and/or COX-2, such as ibuprofen, dextromethorphan, and N-G-methyl-L-arginine (L-NMA), show negligible effects on microglial A beta phagocytosis. Among the thiourea derivatives, our data show that a lead compound, designated as compound #326, (1-Naphthalen-1-yl-3[5-(3-thioureidophenoxy)-pentyl]-thiourea) appears to be the most potent in promoting A beta phagocytosis and in inhibiting the LPS-induced expression of iNOS and COX-2 (when used at concentrations in the low mu M range). The potency of compound #326 may have beneficial effects on modulating microglial activation in AD. The structure-activity relationship indicates that the thiourea group, alkyl linker, and the hydrophobic aryl group largely influence the dual functions of the compounds. These findings may indicate a structural basis for the improved design of future drug therapies for AD. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.cbi.2010.07.006
• 作为产物：
  描述：

  1-naphthalen-1-yl-3-[5-(3-nitro-phenoxy)-pentyl]-thiourea 在 tin(II) chloride dihydrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1-[5-(3-amino-phenoxy)-pentyl]-3-naphthalen-1-yl-thiourea
  参考文献：
  名称：

  设计和有效合成新型的芳硫脲衍生物作为有效的丙型肝炎病毒抑制剂

  摘要：

  设计并合成了一类新型的芳基硫脲HCV抑制剂，其在烷基连接基上具有各种功能，例如环脲，环硫脲，尿素和硫脲。在本文中，我们报告了这种新型的芳基硫脲衍生物的合成及其构效关系（SAR），这些衍生物在基于细胞的亚基因组HCV复制子测定中显示出对HCV的有效抑制活性。在测试的化合物中，发现新的咔唑衍生物64具有很强的抗HCV活性（EC 50  = 0.031），该咔唑衍生物在苯基和咔唑环之间具有八个碳原子的连接，并且在咔唑的N-9位具有甲苯基。μM），较低的细胞毒性（CC 50 > 50μM）和较高的选择性指数（SI> 1612）。

  DOI：

  10.1016/j.bmcl.2009.09.037

文献信息

• Design and efficient synthesis of novel arylthiourea derivatives as potent hepatitis C virus inhibitors
  作者：Iou-Jiun Kang、Li-Wen Wang、Sheng-Ju Hsu、Chung-Chi Lee、Yen-Chun Lee、Yen-Shian Wu、Andrew Yueh、Jing-Chyi Wang、Tsu-An Hsu、Yu-Sheng Chao、Jyh-Haur Chern

  DOI：10.1016/j.bmcl.2009.09.037

  日期：2009.11

  alkyl linker were designed and synthesized. Herein we report the synthesis and structure–activity relationships (SARs) of this novel class of arylthiourea derivatives that showed potent inhibitory activities against HCV in the cell-based subgenomic HCV replicon assay. Among compounds tested, the new carbazole derivative 64, which has an eight-carbon linkage between the phenyl and carbazole rings and a tolyl

  设计并合成了一类新型的芳基硫脲HCV抑制剂，其在烷基连接基上具有各种功能，例如环脲，环硫脲，尿素和硫脲。在本文中，我们报告了这种新型的芳基硫脲衍生物的合成及其构效关系（SAR），这些衍生物在基于细胞的亚基因组HCV复制子测定中显示出对HCV的有效抑制活性。在测试的化合物中，发现新的咔唑衍生物64具有很强的抗HCV活性（EC 50  = 0.031），该咔唑衍生物在苯基和咔唑环之间具有八个碳原子的连接，并且在咔唑的N-9位具有甲苯基。μM），较低的细胞毒性（CC 50 > 50μM）和较高的选择性指数（SI> 1612）。
• THIOUREA DERIVATIVES
  申请人：Chern Jyh-Haur

  公开号：US20080306090A1

  公开（公告）日：2008-12-11

  Thiourea compounds of the following formula: wherein n, R 1 , R 2 , R 3 , A 1 , A 2 , X, Y, and Z are defined herein. Also disclosed is a method of treating hepatitis C virus infection with these compounds.

  以下式的硫脲化合物：其中n、R1、R2、R3、A1、A2、X、Y和Z在此处定义。还公开了使用这些化合物治疗丙型肝炎病毒感染的方法。
• Treatment of Neurodegenerative Disorders with Thiourea Compounds
  申请人：Shie Feng-Shiun

  公开号：US20090275596A1

  公开（公告）日：2009-11-05

  A method for treating a neurodegenerative disorder. The method includes administering to a subject in need thereof an effective amount of one or more thiourea compounds of formula (I) or (II): Each variable in formula (I) or (II) is defined herein. Also disclosed is use of these thiourea compounds to reduce microglia-mediated neuro-inflammation or enhancing microglial phagocytosis of Aβ.

  一种治疗神经退行性疾病的方法。该方法包括向需要的受试者施用一种或多种硫脲化合物的有效量，其化学式为(I)或(II)：化学式(I)或(II)中的每个变量在此有定义。还公开了利用这些硫脲化合物来减少微胶质细胞介导的神经炎症或增强微胶质细胞对Aβ的吞噬能力。
• US7897764B2
  申请人：——

  公开号：US7897764B2

  公开（公告）日：2011-03-01
• US8198284B2
  申请人：——

  公开号：US8198284B2

  公开（公告）日：2012-06-12