4-(4-chlorophenyl)-N-(naphthalen-1-yl)thiazol-2-amine | 284668-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(4-chlorophenyl)-N-(naphthalen-1-yl)thiazol-2-amine
• 英文别名: 4-(4-Chlorophenyl)-N-1-Naphthalenyl-2-thiazolamine；4-(4-chlorophenyl)-N-naphthalen-1-yl-1,3-thiazol-2-amine
• CAS: 284668-45-7
• 化学式: C₁₉H₁₃ClN₂S
• 分子量: 336.845
• InChiKey: MHGCDBNQFDHVEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  535.5±42.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  安妥 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醇 为溶剂， 反应 0.17h， 生成 4-(4-chlorophenyl)-N-(naphthalen-1-yl)thiazol-2-amine
  参考文献：
  名称：

  Synthesis and biological activity of 2-aminothiazoles as novel inhibitors of PGE2 production in cells

  摘要：

  This Letter presents the synthesis and biological evaluation of a collection of 2-aminothiazoles as a novel class of compounds with the capability to reduce the production of PGE(2) in HCA-7 human adenocarcinoma cells. A total of 36 analogs were synthesized and assayed for PGE(2) reduction, and those with potent cellular activity were counter screened for inhibitory activity against COX-2 in a cell free assay. In general, analogs bearing a 4-phenoxyphenyl substituent in the R-2 position were highly active in cells while maintaining negligible COX-2 inhibition. Specifically, compound 5l (R-1 = Me, R-2 = 4-OPh-Ph, R-3 = CH(OH)Me) exhibited the most potent cellular PGE(2) reducing activity of the entire series (EC50 = 90 nM) with an IC50 value for COX-2 inhibition of >5 mu M in vitro. Furthermore, the anti-tumor activity of analog 1a was analyzed in xenograft mouse models exhibiting promising anti-cancer activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.013

文献信息

• Aryliodoazide Synthons: A Different Approach for Diversified Synthesis of 2-Aminothiazole, 1,3-Thiazole, and 1,3-Selenazole Scaffolds
  作者：Sahar Majnooni、Joseph Duffield、Jessica Price、Ahmad Reza Khosropour、Hassan Zali-Boeini、Hudson Beyzavi

  DOI：10.1021/acscombsci.9b00045

  日期：2019.7.8

  Several straightforward and practical processes have been established for the construction of 2-aminothiazoles, 1,3-thiazoles and 1,3-selenazoles from aryliodoazides. These strategies successfully proceed with a wide spectrum of substituted thioamides and its derivatives producing the resulting five-membered heterocycles obtained in satisfactory yields. The unique features of these protocols are operational

  已经建立了几种直接且实用的方法来从芳基碘化物构建 2-氨基噻唑、1,3-噻唑和 1,3-硒唑。这些策略成功地使用了广泛的取代硫代酰胺及其衍生物，产生了以令人满意的产率获得的五元杂环。这些协议的独特之处在于操作简单和高度官能团耐受性，这使其成为制备各种 2-氨基噻唑、1,3-噻唑和 1,3-硒唑库的方便实用的途径。
• US7262204B2
  申请人：——

  公开号：US7262204B2

  公开（公告）日：2007-08-28
• Synthesis and biological activity of 2-aminothiazoles as novel inhibitors of PGE2 production in cells
  作者：Breland Smith、Hui-Hua Chang、Federico Medda、Vijay Gokhale、Justin Dietrich、Angela Davis、Emmanuelle J. Meuillet、Christopher Hulme

  DOI：10.1016/j.bmcl.2012.03.013

  日期：2012.5

  This Letter presents the synthesis and biological evaluation of a collection of 2-aminothiazoles as a novel class of compounds with the capability to reduce the production of PGE(2) in HCA-7 human adenocarcinoma cells. A total of 36 analogs were synthesized and assayed for PGE(2) reduction, and those with potent cellular activity were counter screened for inhibitory activity against COX-2 in a cell free assay. In general, analogs bearing a 4-phenoxyphenyl substituent in the R-2 position were highly active in cells while maintaining negligible COX-2 inhibition. Specifically, compound 5l (R-1 = Me, R-2 = 4-OPh-Ph, R-3 = CH(OH)Me) exhibited the most potent cellular PGE(2) reducing activity of the entire series (EC50 = 90 nM) with an IC50 value for COX-2 inhibition of >5 mu M in vitro. Furthermore, the anti-tumor activity of analog 1a was analyzed in xenograft mouse models exhibiting promising anti-cancer activity. (C) 2012 Elsevier Ltd. All rights reserved.