Gallussaeure-<4-nitro-anilid> | 109041-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Gallussaeure-<4-nitro-anilid>
• 英文别名: 3,4,5-trihydroxy-N-(4-nitrophenyl)benzamide
• CAS: 109041-70-5
• 化学式: C₁₃H₁₀N₂O₆
• 分子量: 290.232
• InChiKey: JYIUNLUTPUEHRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  没食子酸 、 4-硝基苯胺 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以49 %的产率得到Gallussaeure-<4-nitro-anilid>
  参考文献：
  名称：

  Synthesis, in vitro and in silico evaluation of gallamide and selenogallamide derivatives as inhibitors of the SARS‐CoV‐2 main protease

  摘要：

  The present work reports the inhibitory effect of amides derived from gallic acid (gallamides) against severe acute respiratory syndrome coronavirus 2 (SARS‐CoV‐2) main protease (Mpro), along with cytotoxicity evaluation and molecular docking studies. In addition to gallamides, other relevant compounds were also synthesized and evaluated against Mpro, making a total of 25 compounds. Eight compounds presented solubility issues during the inhibitory assay and one showed no inhibitory activity. Compounds 3a, 3b, and 3f showed the highest enzymatic inhibition with IC50 = 0.26 ± 0.19 µM, 0.80 ± 0.38 µM, and 2.87 ± 1.17 µM, respectively. Selenogallamide 6a exhibited IC50 values of 5.42 ± 2.89 µM and a comparison with its nonselenylated congener 3c shows that the insertion of the chalcogen moiety improved the inhibitory capacity of the compound by approximately 10 times. Regarding the cellular toxicity in THP‐1 and Vero cells, compounds 3e and 3g, showed moderate cytotoxicity in Vero cells, while for THP‐1 both were nontoxic, with CC50 > 150 µM. Derivative 3d showed moderate cytotoxicity against both cell lines, whereas 6d was moderatly toxic to THP‐1. Other compounds analyzed do not induce substantial cellular toxicity at the concentrations tested. The molecular docking results for compounds 3a, 3b, and 3f show that hydrogen bonding interactions involving the hydroxyl groups (OH) of the gallate moiety are relevant, as well as the carbonyl group.

  DOI：

  10.1002/ardp.202400253