ethyl 2-(thiophene-2-yl)-1,3-oxazole-4-carboxylate | 54679-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(thiophene-2-yl)-1,3-oxazole-4-carboxylate
• 英文别名: ethyl 2-(thiophen-2-yl)oxazole-4-carboxylate；ethyl 2-thiophen-2-yl-1,3-oxazole-4-carboxylate
• CAS: 54679-18-4
• 化学式: C₁₀H₉NO₃S
• 分子量: 223.252
• InChiKey: USBVSKGMUFFOSF-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  349.4±40.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.33
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(thiophene-2-yl)-1,3-oxazole-4-carboxylate 在 N-甲基吗啉 、 氯甲酸乙酯 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.67h， 生成 2-(thiophene-2-yl)-1,3-oxazole-4-carbohydroxamic acid
  参考文献：
  名称：

  Synthesis and Biological Investigation of Oxazole Hydroxamates as Highly Selective Histone Deacetylase 6 (HDAC6) Inhibitors

  摘要：

  Histone deacetylase 6 (HDAC6) catalyzes the removal of an acetyl group from lysine residues of several nonhistone proteins. Here we report the preparation of thiazole-, oxazole-, and oxadiazole-containing biarylhydroxamic acids by a short synthetic procedure. We identified them as selective HDAC6 inhibitors by investigating the inhibition of B recombinant HDAC enzymes and the protein acetylation in cells by Western blotting (tubulin vs histone acetylation). The most active compounds exhibited nanomolar potency and high selectivity for HDAC6. For example, an oxazole hydroxamate inhibits HDAC6 with an IC50 of 59 nM and has a selectivity index of >200 against HDAC1 and HDAC8. This is the first report showing that the nature of a heterocycle directly connected to a zinc binding group (ZBG) can be used to modulate subtype selectivity and potency for HDAC6 inhibitors to such an extent. We rationalize the high potency and selectivity of the oxazoles by molecular modeling and docking.

  DOI：

  10.1021/acs.jmedchem.5b01493
• 作为产物：
  描述：

  2-氯噻吩 、 4-恶唑甲酸乙酯 在 palladium diacetate 、 caesium carbonate 、 三(邻甲基苯基)磷 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以97%的产率得到ethyl 2-(thiophene-2-yl)-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  钯催化的恶唑-4-羧酸乙酯的直接（杂）芳基化：一种（杂）芳基恶唑的有效途径。

  摘要：

  通过区域控制的钯催化的恶唑-4-羧酸乙酯与碘，溴和氯（杂）的直接（杂）芳基化反应，生成2-（杂）芳基化和2,5-二（杂）芳基恶唑的直接途径描述了芳族化合物，随后是两步水解/脱羧序列。该方法在这里用于两种2,5-二（杂）芳基恶唑天然产物balsoxin和texaline的纯净合成。

  DOI：

  10.1021/jo801093n

文献信息

• Pd-catalyzed desulfitative arylation for the synthesis of 2,5-diarylated oxazole-4-carboxylates using dioxygen as the terminal oxidant
  作者：Xiaodong Tang、Kai Yang、Liying Zeng、Qiang Liu、Huoji Chen

  DOI：10.1039/c7ob01912b

  日期：——

  A novel palladium-catalyzed approach for constructing 2,5-diarylated oxazole-4-carboxylates using sodium arylsulfinates as the aryl source has been demonstrated.

  一种新颖的钯催化方法已被证明可用于利用亚砜酸钠作为芳基来源构建2,5-二芳基氧唑-4-羧酸酯。
• A Silver-Mediated One-Step Synthesis of Oxazoles
  作者：Dougal J. Ritson、Christian Spiteri、John E. Moses

  DOI：10.1021/jo1025332

  日期：2011.5.6

  A silver-mediated one-step procedure to 2,4-disubstituted and 2,4,5-trisubstituted oxazoles has been developed. The method is complementary to existing technologies, yet provides advantages with regard to simplicity, efficiency, and performance. The silver product can be readily recycled, thus minimizing waste.

  已经开发了银介导的2,4-二取代和2,4,5-三取代的恶唑的一步法。该方法是对现有技术的补充，但在简单性，效率和性能方面提供了优势。银产品可以很容易地回收利用，从而减少了浪费。