乙基2-(3-氰基-4-异丁氧基苯基)-4-甲基-1,3-噻唑-5-羧酸酯 | 144060-97-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 乙基2-(3-氰基-4-异丁氧基苯基)-4-甲基-1,3-噻唑-5-羧酸酯
• 中文别名: 2-(3-氰基-4-异丁氧基苯基)-4-甲基噻唑-5-甲酸乙酯
• 英文名称: ethyl 2-(4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate
• 英文别名: 3-Descyano Febuxostat Ethyl Ester；ethyl 4-methyl-2-[4-(2-methylpropoxy)phenyl]-1,3-thiazole-5-carboxylate
• CAS: 144060-97-9
• 化学式: C₁₇H₂₁NO₃S
• 分子量: 319.425
• InChiKey: LJRMNYUTCKYZJR-UHFFFAOYSA-N

物化性质

• 沸点：
  438.3±55.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  76.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙基2-(3-氰基-4-异丁氧基苯基)-4-甲基-1,3-噻唑-5-羧酸酯 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以88%的产率得到2-(4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, in silico and in vitro studies of novel 4-methylthiazole-5-carboxylic acid derivatives as potent anti-cancer agents

  摘要：

  (S)ince inhibitors of mucin onco proteins are potential targets for breast cancer therapy, a series of novel 4-methylthiazole-5-carboxylic acid (1) derivatives 3a-k were synthesized by the reaction of 1 with SOCl2 followed by different bases/alcohols in the presence of triethylamine. Once synthesized and characterized, their binding modes with MUC1 were studied by molecular docking analysis using Aruglab 4.0.1 and QSAR properties were determined using HyperChem. All synthesized compounds were screened for in vitro anti-breast cancer activity against MDA-MB-231 breast adenocarcinoma cell lines by Trypan-blue cell viability assay and MTT methods. Compounds 1, 3b, 3d, 3e, 3i and 3f showed good anti-breast cancer activity. Since 1 and 3d exhibited high potent activity against MDA-MB-231 cell lines, they show could be effective mucin onco protein inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.058
• 作为产物：
  描述：

  2-(4-羟基苯基)-4-甲基噻唑-5-羧酸乙酯 、 溴代异丁烷 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 2.0h， 以83%的产率得到乙基2-(3-氰基-4-异丁氧基苯基)-4-甲基-1,3-噻唑-5-羧酸酯
  参考文献：
  名称：

  Design, synthesis, in silico and in vitro studies of novel 4-methylthiazole-5-carboxylic acid derivatives as potent anti-cancer agents

  摘要：

  (S)ince inhibitors of mucin onco proteins are potential targets for breast cancer therapy, a series of novel 4-methylthiazole-5-carboxylic acid (1) derivatives 3a-k were synthesized by the reaction of 1 with SOCl2 followed by different bases/alcohols in the presence of triethylamine. Once synthesized and characterized, their binding modes with MUC1 were studied by molecular docking analysis using Aruglab 4.0.1 and QSAR properties were determined using HyperChem. All synthesized compounds were screened for in vitro anti-breast cancer activity against MDA-MB-231 breast adenocarcinoma cell lines by Trypan-blue cell viability assay and MTT methods. Compounds 1, 3b, 3d, 3e, 3i and 3f showed good anti-breast cancer activity. Since 1 and 3d exhibited high potent activity against MDA-MB-231 cell lines, they show could be effective mucin onco protein inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.058

文献信息

• Photo- and Cu-Mediated 11C Cyanation of (Hetero)Aryl Thianthrenium Salts
  作者：Kevin Cheng、E. William Webb、Gregory D. Bowden、Jay S. Wright、Xia Shao、Melanie S. Sanford、Peter J. H. Scott

  DOI：10.1021/acs.orglett.4c00929

  日期：2024.4.26

  We present a photo- and Cu-mediated 11C cyanation of bench-stable (hetero)aryl thianthrenium salts via an aryl radical addition pathway. The thianthrenium substrates can be readily accessed via C–H functionalization, and the radiocyanation protocol proceeds under mild conditions (<50 °C, 5 min) and can be automated using open-source, readily accessible augmentations to existing radiochemistry equipment

  我们提出了通过芳基自由基加成途径对实验室稳定的（杂）芳基噻烯盐进行光和铜介导的11 C 氰化。铊底物可以通过 C-H 官能化轻松获得，放射氰化方案在温和条件下（<50°C，5 分钟）进行，并且可以使用开源、易于访问的现有放射化学设备增强功能实现自动化。
• 2-ARYLTHIAZOLE DERIVATIVE AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
  申请人：TEIJIN LIMITED

  公开号：EP0513379B1

  公开（公告）日：1996-09-11
• US5614520A
  申请人：——

  公开号：US5614520A

  公开（公告）日：1997-03-25