2-(3-methoxyphenyl)-5-methyl-1,3-oxazole-4-carboxylic acid | 355020-54-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-methoxyphenyl)-5-methyl-1,3-oxazole-4-carboxylic acid
• 英文别名: 2-(3-Methoxyphenyl)-5-methyloxazole-4-carboxylic Acid
• CAS: 355020-54-1
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: XTYMMVFYCQHLFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-吡啶甲基)甘氨酸乙酯 、 2-(3-methoxyphenyl)-5-methyl-1,3-oxazole-4-carboxylic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Towards Gram-negative antivirulence drugs: New inhibitors of HldE kinase

  摘要：

  Gram-negative bacteria lacking heptoses in their lipopolysaccharide (LPS) display attenuated virulence and increased sensitivity to human serum and to some antibiotics. Thus inhibition of bacterial heptose synthesis represents an attractive target for the development of new antibacterial agents. HldE is a bifunctional enzyme involved in the synthesis of bacterial heptoses. Development of a biochemical assay suitable for high-throughput screening allowed the discovery of inhibitors 1 and 2 of HldE kinase. Study of the structure-activity relationship of this series of inhibitors led to highly potent compounds. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.021
• 作为产物：
  描述：

  在 lithium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-(3-methoxyphenyl)-5-methyl-1,3-oxazole-4-carboxylic acid
  参考文献：
  名称：

  Towards Gram-negative antivirulence drugs: New inhibitors of HldE kinase

  摘要：

  Gram-negative bacteria lacking heptoses in their lipopolysaccharide (LPS) display attenuated virulence and increased sensitivity to human serum and to some antibiotics. Thus inhibition of bacterial heptose synthesis represents an attractive target for the development of new antibacterial agents. HldE is a bifunctional enzyme involved in the synthesis of bacterial heptoses. Development of a biochemical assay suitable for high-throughput screening allowed the discovery of inhibitors 1 and 2 of HldE kinase. Study of the structure-activity relationship of this series of inhibitors led to highly potent compounds. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.021

文献信息

• Discovery of a Novel Small-Molecule Inhibitor Disrupting TRBP–Dicer Interaction against Hepatocellular Carcinoma via the Modulation of microRNA Biogenesis
  作者：Ting Peng、Yujiao He、Tao Wang、Jialing Yu、Xiaofang Ma、Zongyuan Zhou、Yuwen Sheng、Lingyu Li、Huipan Peng、Sheng Li、Jiawei Zou、Yi Yuan、Yongyun Zhao、Hailong Shi、Fu Li、Wanli Liu、Kaifeng Hu、Xiaoxia Lu、Guolin Zhang、Fei Wang

  DOI：10.1021/acs.jmedchem.2c00189

  日期：2022.8.25

  players in human hepatocellular carcinoma (HCC) tumorigenesis. Therefore, small molecules targeting components of miRNA biogenesis may provide new therapeutic means for HCC treatment. By a high-throughput screening and structural simplification, we identified a small molecule, CIB-3b, which suppresses the growth and metastasis of HCC in vitro and in vivo by modulating expression profiles of miRNAome and

  MicroRNAs (miRNAs) 是人类肝细胞癌 (HCC) 肿瘤发生的关键参与者。因此，靶向miRNA生物发生成分的小分子可能为HCC的治疗提供新的治疗手段。通过高通量筛选和结构简化，我们鉴定了一种小分子 CIB-3b，它在体外和体内抑制 HCC 的生长和转移通过调节 HCC 细胞中 miRNA 组和蛋白质组的表达谱。从机制上讲，CIB-3b 与反式激活反应 (TAR) RNA 结合蛋白 2 (TRBP) 物理结合并破坏 TRBP-Dicer 相互作用，从而改变 Dicer 的活性和成熟 miRNA 的产生。通过合成 45 种 CIB-3b 衍生物的构效关系研究表明，一些化合物对 miRNA 生物发生的抑制作用与 CIB-3b 相似。这些结果支持 TRBP 作为 HCC 的潜在治疗靶点，并需要进一步开发 CIB-3b 及其类似物作为治疗 HCC 的新治疗策略。
• Towards Gram-negative antivirulence drugs: New inhibitors of HldE kinase
  作者：Nicolas Desroy、François Moreau、Sophia Briet、Géraldine Le Fralliec、Stephanie Floquet、Lionel Durant、Vanida Vongsouthi、Vincent Gerusz、Alexis Denis、Sonia Escaich

  DOI：10.1016/j.bmc.2008.12.021

  日期：2009.2

  Gram-negative bacteria lacking heptoses in their lipopolysaccharide (LPS) display attenuated virulence and increased sensitivity to human serum and to some antibiotics. Thus inhibition of bacterial heptose synthesis represents an attractive target for the development of new antibacterial agents. HldE is a bifunctional enzyme involved in the synthesis of bacterial heptoses. Development of a biochemical assay suitable for high-throughput screening allowed the discovery of inhibitors 1 and 2 of HldE kinase. Study of the structure-activity relationship of this series of inhibitors led to highly potent compounds. (c) 2008 Elsevier Ltd. All rights reserved.