4-bromothiazole-5-carboxylic acid | 1244949-48-1

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-bromothiazole-5-carboxylic acid
• 英文别名: 4-bromo-1,3-thiazole-5-carboxylic acid
• CAS: 1244949-48-1
• 化学式: C₄H₂BrNO₂S
• mdl: MFCD11111596
• 分子量: 208.035
• InChiKey: GQCIIZJOGXFYNG-UHFFFAOYSA-N

物化性质

• 沸点：
  367.7±27.0 °C(Predicted)
• 密度：
  2.062

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氨基苯基苯甲酮 、 4-bromothiazole-5-carboxylic acid 在 polymer-bound EDC 作用下， 生成 4-Bromo-thiazole-5-carboxylic acid (3-benzoyl-phenyl)-amide
  参考文献：
  名称：

  Utility of Complementary Molecular Reactivity and Molecular Recognition (CMR/R) Technology and Polymer-Supported Reagents in the Solution-Phase Synthesis of Heterocyclic Carboxamides

  摘要：

  The use of our recently reported chemical library purification strategy in the development of a herbicidal lead, N-(3-benzoylphenyl)-3-(1,1-dimethylethyl)-1-methyl-1H-pyrazole-5-carboxamide (3), is described. The approach applying fundamental properties of complementary molecular reactivity and molecular recognition (CMR/R) as the basis for a general purification strategy was utilized. Polymeric reagents were used in the synthesis to generate reactive species involved in product formation, and complementary molecular reactivity/molecular recognition polymer 8 (CMR/R polymer 8) was used in the solution-phase syntheses of building blocks, primary libraries, and lead refinement libraries. An extension of the CMR/R methodology was applied, utilizing a sequestration enabling reagent (SER), transforming a reactant into an electrophilic species sequestrable by CMR/R polymer 8. This library purification strategy enabled rapid lead generation and lead refinement to afford herbicide 27o. The CMR/R solid-phase purification technique enabled a simple, general, and powerful protocol, eliminating the usual tedious and time-consuming methods required for solution-phase product purification. The result was the synthesis of hundreds of compounds, prepared in a relatively short time, leading to a compound with a 4-fold improvement in herbicidal activity over the initial lead.

  DOI：

  10.1021/jo970571i

文献信息

• Discovery of the novel Benzo[b]thiophene 1,1-dioxide derivatives as a potent STAT3 inhibitor against idiopathic pulmonary fibrosis
  作者：Yijie Wang、Hongyao Liu、Wenzhen Li、Yuting Xie、Cailing Gan、Taixiong Xue、Xingping Su、Lin Yue、Qin Wang、Chen Fan、Yiwen Zhang、Tinghong Ye

  DOI：10.1016/j.ejmech.2022.114953

  日期：2023.1

  Idiopathic pulmonary fibrosis (IPF) is a chronic, progressive lung disease of unknown aetiology with limited treatment options. Currently, only two drugs, nintedanib and pirfenidone, are approved for the clinical treatment of IPF, but their efficacies are not satisfactory. Previous studies have shown that STAT3 might be a promising therapeutic target for IPF. Here, we designed several series of compounds

  特发性肺纤维化（IPF）是一种病因不明且治疗选择有限的慢性进行性肺部疾病。目前只有尼达尼布和吡非尼酮两种药物获批用于临床治疗IPF，但疗效并不理想。先前的研究表明 STAT3 可能是 IPF 的一个有前途的治疗靶点。在这里，我们设计了多个系列的化合物，最终合成了总共48个新化合物作为潜在的STAT3抑制剂。值得注意的是，化合物10K是最有前途的化合物，具有优异的 STAT3 磷酸化抑制活性。随后，通过TGF-β1刺激的体外细胞测定和博莱霉素（BLM）诱导的肺纤维化动物模型进一步研究了10K的抗肺纤维化作用。具体而言，化合物10K抑制TGF-β1诱导的纤维化反应，阻断A549细胞的上皮间质转化（EMT），其抑制效果明显优于STattic。此外，口服10K后，防治小鼠模型肺组织IPF症状明显逆转，疗效与尼达尼布相当。此外，10K改善了 BLM 引起的肺组织免疫微环境失衡。综上所述，这些结果表明10K可能是治疗
• A New Class of Diaryl Ether Herbicides: Structure–Activity Relationship Studies Enabled by a Rapid Scaffold Hopping Approach
  作者：Christopher A. Kalnmals、Zoltan L. Benko、Adel Hamza、Karla Bravo-Altamirano、Thomas L. Siddall、Moriah Zielinski、Hudson K. Takano、Dilpreet S. Riar、Norbert M. Satchivi、Joshua J. Roth、Jeffrey B. Church

  DOI：10.1021/acs.jafc.3c01285

  日期：2023.11.29

  development of a novel class of diaryl ether herbicides. After the discovery of a phenoxybenzoic acid with modest herbicidal activity, optimization led to several molecules with improved control of broadleaf and grass weeds. To facilitate this process, we first employed a three-step combinatorial approach, then pivoted to a one-step Ullmann-type coupling that provided faster access to new analogs. After determining

  我们报告了一类新型二芳基醚除草剂的开发。在发现具有适度除草活性的苯氧基苯甲酸后，优化产生了几种对阔叶杂草和禾本科杂草具有更好控制效果的分子。为了促进这一过程，我们首先采用三步组合方法，然后转向一步乌尔曼型耦合，以更快地获得新的类似物。在确定我们的基准二芳基醚的主要靶位点是乙酰乳酸合酶（ALS）后，我们进一步利用这种铜催化的方法进行支架跳跃活动，希望发现一种具有较少记录的耐药病例的额外作用模式。我们全面、系统的研究表明，虽然该领域的除草活性似乎与 ALS 抑制完全相关，但我们的分子代表了结构独特的 2 类除草剂。本文描述了导致我们得出这一结论的结构-活性关系。