4-bromo-2-methylthiazole-5-carbaldehyde

• 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-bromo-2-methylthiazole-5-carbaldehyde
• 英文别名: 4-Bromo-2-methylthiazole-5-carbaldehyde；4-bromo-2-methyl-1,3-thiazole-5-carbaldehyde
• 化学式: C₅H₄BrNOS
• 分子量: 206.063
• InChiKey: UCYOVUOHHVAUHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-2-methylthiazole-5-carbaldehyde 在 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 34.0h， 生成 tert-butyl ((4-bromo-2-methylthiazol-5-yl)methyl)(methyl)carbamate
  参考文献：
  名称：

  [EN] TYK2 INHIBITORS AND USES THEREOF
  [FR] INHIBITEURS DE TYK2 ET LEURS UTILISATIONS

  摘要：

  Described herein are compounds that are TYK2 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders that would benefit from modulation of TYK2 activity. Formula (I):

  公开号：

  WO2023227946A1
• 作为产物：
  描述：

  4-bromo-N-methoxy-N,2-dimethylthiazole-5-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以7.7 g的产率得到4-bromo-2-methylthiazole-5-carbaldehyde
  参考文献：
  名称：

  [EN] TYK2 INHIBITORS AND USES THEREOF
  [FR] INHIBITEURS DE TYK2 ET LEURS UTILISATIONS

  摘要：

  Described herein are compounds that are TYK2 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders that would benefit from modulation of TYK2 activity. Formula (I):

  公开号：

  WO2023227946A1

文献信息

• [EN] HETEROAROMATIC MACROCYCLIC ETHER CHEMOTHERAPEUTIC AGENTS<br/>[FR] AGENTS CHIMIOTHÉRAPEUTIQUES À BASE D'ÉTHER MACROCYCLIQUE HÉTÉROAROMATIQUE
  申请人：NUVALENT INC

  公开号：WO2021226269A1

  公开（公告）日：2021-11-11

  Disclosed are heterocyclic heteroaromatic macrocyclic ether compounds, pharmaceutically acceptable salts of the compounds and pharmaceutical compositions thereof. Also disclosed are methods of treating or preventing cancer using the heterocyclic heteroaromatic macrocyclic ether compounds, pharmaceutically acceptable salts of the compounds, and pharmaceutical compositions thereof.

  揭示了杂环杂芳大环醚化合物，这些化合物的药用盐以及它们的药物组合物。还揭示了使用这些杂环杂芳大环醚化合物、这些化合物的药用盐以及它们的药物组合物来治疗或预防癌症的方法。
• DPD-Inspired Discovery of Novel LsrK Kinase Inhibitors: An Opportunity To Fight Antimicrobial Resistance
  作者：Silvia Stotani、Viviana Gatta、Prasanthi Medarametla、Mohan Padmanaban、Anna Karawajczyk、Fabrizio Giordanetto、Päivi Tammela、Tuomo Laitinen、Antti Poso、Dimitros Tzalis、Simona Collina

  DOI：10.1021/acs.jmedchem.9b00025

  日期：2019.3.14

  Antibiotic resistance is posing a continuous threat to global public health and represents a huge burden for society as a whole. In the past decade, the interference with bacterial quorum sensing (QS) (i.e., cell cell communication) mechanisms has extensively been investigated as a valid therapeutic approach in the pursuit of a next generation of antimicrobials. (S)-4,5-Dihydroxy-2,3-pentanedione, commonly known as (S)-DPD, a small signaling molecule that modulates QS in both Gram-negative and Gram-positive bacteria, is phosphorylated by LsrK, and the resulting phospho-DPD activates QS. We designed and prepared a small library of DPD derivatives, characterized by five different scaffolds, and evaluated their LsrK inhibition in the context of QS interference. SAR studies highlighted the pyrazole moiety as an essential structural element for LsrK inhibition. Particularly, four compounds were found to be micromolar LsrK inhibitors (IC50 ranging between 100 mu M and 500 mu M) encouraging further exploration of novel analogues as potential new antimicrobials.