2-(N-(p-methoxy)phenylamino)-4-((p-methoxy)phenyl)thiazole | 315707-02-9

• 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: 2-(N-(p-methoxy)phenylamino)-4-((p-methoxy)phenyl)thiazole
• 英文别名: ChemBridge ID 5935487；N,4-bis(4-methoxyphenyl)-1,3-thiazol-2-amine
• CAS: 315707-02-9
• 化学式: C₁₇H₁₆N₂O₂S
• 分子量: 312.392
• InChiKey: PTHCHNRYBATMST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  alpha-溴-4-甲氧基苯乙酮 、 对甲氧基苯基硫脲 在 choline chloride-urea 作用下， 以 水 为溶剂， 反应 0.33h， 以91%的产率得到2-(N-(p-methoxy)phenylamino)-4-((p-methoxy)phenyl)thiazole
  参考文献：
  名称：

  Lipase and Deep Eutectic Mixture Catalyzed Efficient Synthesis of Thiazoles in Water at Room Temperature

  摘要：

  Lipase bio-catalyst or ammonium based deep eutectic mixture efficiently catalyzed aqueous phase synthesis of methyl-thiazole and amino-thiazole derivatives. The simple ammonium deep eutectic catalyst, easily synthesized from choline chloride and urea, is inexpensive, recyclable and bio-degradable, making it suitable for industrial applications.

  DOI：

  10.1007/s10562-012-0902-5

文献信息

• Effect of Substituents on the Regioselectivity of the Reaction of α-Tosyloxyketones with Thioureas in Acidic Medium: Access to 2-Aminothiazoles and 2-Imino-2,3-dihydrothiazoles
  作者：Ranjana Aggarwal、Rajiv Kumar、Dionisia Sanz、Rosa M. Claramunt

  DOI：10.1002/jhet.1676

  日期：2014.5

  Regioselective condensation of α‐tosyloxyacetophenones 1 and N‐substituted thioureas 2 in acidic medium to give regioisomers 2‐aminothiazoles I and 2‐imino‐2,3‐dihydrothiazoles II is largely influenced by the substituents present on 1 and 2. A mechanism, supported by DFT calculations has been proposed to explain the observed regioselectively.

  α-甲苯磺酰氧基苯乙酮1和N-取代的硫脲2在酸性介质中的区域选择性缩合反应产生区域异构体2-氨基噻唑I和2-亚氨基-2,3-二氢噻唑II在很大程度上受到1和2上存在的取代基的影响。已经提出了一种由DFT计算支持的机制来选择性地解释所观察到的区域。
• COMPOUNDS AND USES THEREOF IN MODULATING AMYLOID BETA
  申请人：Cheng Soan

  公开号：US20100324032A1

  公开（公告）日：2010-12-23

  Novel compounds, compositions, and kits are provided. Methods of modulating Aβ levels, and methods of treating a disease associated with aberrant Aβ levels are also provided.

  本发明提供了新型化合物、组合物和试剂盒。还提供了调节Aβ水平的方法和治疗与异常Aβ水平相关的疾病的方法。
• 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.
• US7244739B2
  申请人：——

  公开号：US7244739B2

  公开（公告）日：2007-07-17
• US8017629B2
  申请人：——

  公开号：US8017629B2

  公开（公告）日：2011-09-13