(2E)-3-(6-methyl-1,3-benzoxazol-2-yl)prop-2-enoic acid | 1413431-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: (2E)-3-(6-methyl-1,3-benzoxazol-2-yl)prop-2-enoic acid
• 英文别名: (E)-3-(6-methylbenzo[d]oxazol-2-yl)acrylic acid；(2e)-3-(6-Methyl-1,3-benzoxazol-2-yl)prop-2-enoic acid；(E)-3-(6-methyl-1,3-benzoxazol-2-yl)prop-2-enoic acid
• CAS: 1413431-71-6
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: YXYSWKINELDVJX-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  马来酸酐 、 6-氨基间甲酚 在 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以42%的产率得到(2E)-3-(6-methyl-1,3-benzoxazol-2-yl)prop-2-enoic acid
  参考文献：
  名称：

  Synthesis and theoretic calculations of benzoxazoles and docking studies of their interactions with triosephosphate isomerase

  摘要：

  One-pot synthesis was carried out for Z or E stereoisomer derivates of 3-(benzoxazoyl)-2-propenoic acid following kinetic or thermodynamic control. All compounds were characterized by H-1 and C-13 NMR, and the single crystal X-ray structure of (2Z)-3-(6-methyl-1,3-benzoxazol-2-yl)prop-2-enoic acid (3) was obtained. Furthermore, a theoretic study was done for all the synthesized compounds at the B3LYP/6-31G(d,p) level. The target compounds were docked on triosephosphate isomerase and trypanocidal activity was explored for the 4 and 6 compounds. The Z isomers showed an intramolecular hydrogen bond O-H center dot center dot center dot N according to the X-ray structure of 3. The docking studies indicate that the test compounds insert themselves between the monomers of triosephosphate isomerase, reaching the known binding site located at interdimeric shapes of triosephosphate isomerase by means of pi-pi interactions and electrostatic interactions, and in this way interrupt interactions between these monomers. Thus, could explain the biologic effects of the E isomer on triosephosphate isomerase. Finally, compounds 4 and 6 showed trypanocidal activity, which could be mediated by triosephosphate isomerase inhibition.

  DOI：

  10.1007/s00044-012-0264-y

文献信息

• Copper-catalysed one-pot cascade reaction strategy for the synthesis of benzoxazole-2-acrylic acid and benzoxazole-2‑propanoic acid derivatives
  作者：Harendra Kumar、Kaushal Naithani、Priyanka Bhalerao、Bireswar Bhattacharya、Subhendu Bhowmik

  DOI：10.1016/j.tetlet.2023.154514

  日期：2023.6

  A Cu-catalysed cascade strategy has been developed to synthesize benzoxazole-2-acrylic acid and benzoxazole-2‑propanoic acid derivatives in one pot by reacting 2-bromoaniline with maleic anhydride or succinic anhydride. The cascade cyclic anhydride ring opening followed by O-arylation reaction afforded the products in very good yields.

  开发了一种铜催化级联策略，通过使 2-溴苯胺与马来酸酐或琥珀酸酐反应，一锅合成苯并恶唑-2-丙烯酸和苯并恶唑-2-丙酸衍生物。级联环状酸酐开环随后进行O-芳基化反应，以非常高的收率提供产物。
• Synthesis and theoretic calculations of benzoxazoles and docking studies of their interactions with triosephosphate isomerase
  作者：César A. Flores Sandoval、Roberto I. Cuevas Hernández、José Correa Basurto、Hiram I. Beltrán Conde、Itzia I. Padilla Martínez、José N. Farfán García、Benjamín Nogueda Torres、José G. Trujillo Ferrara

  DOI：10.1007/s00044-012-0264-y

  日期：2013.6

  One-pot synthesis was carried out for Z or E stereoisomer derivates of 3-(benzoxazoyl)-2-propenoic acid following kinetic or thermodynamic control. All compounds were characterized by H-1 and C-13 NMR, and the single crystal X-ray structure of (2Z)-3-(6-methyl-1,3-benzoxazol-2-yl)prop-2-enoic acid (3) was obtained. Furthermore, a theoretic study was done for all the synthesized compounds at the B3LYP/6-31G(d,p) level. The target compounds were docked on triosephosphate isomerase and trypanocidal activity was explored for the 4 and 6 compounds. The Z isomers showed an intramolecular hydrogen bond O-H center dot center dot center dot N according to the X-ray structure of 3. The docking studies indicate that the test compounds insert themselves between the monomers of triosephosphate isomerase, reaching the known binding site located at interdimeric shapes of triosephosphate isomerase by means of pi-pi interactions and electrostatic interactions, and in this way interrupt interactions between these monomers. Thus, could explain the biologic effects of the E isomer on triosephosphate isomerase. Finally, compounds 4 and 6 showed trypanocidal activity, which could be mediated by triosephosphate isomerase inhibition.