furan-2-carboxylic acid (4-nitrophenyl)amide | 56049-63-9

• 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: furan-2-carboxylic acid (4-nitrophenyl)amide
• 英文别名: BPR1K0250S0；furan-2-carboxylic acid-(4-nitro-anilide)；Furan-2-carbonsaeure-(4-nitro-anilid)；Furan-2-carbonsaeure-4'-nitroanilid；2-Furyl-4'-nitro-anilid；N-(4-nitrophenyl)-2-furamide；N-(4-nitrophenyl)furan-2-carboxamide
• CAS: 56049-63-9
• 化学式: C₁₁H₈N₂O₄
• mdl: MFCD00446977
• 分子量: 232.196
• InChiKey: CTMRLATWDPKMGM-UHFFFAOYSA-N

物化性质

• 熔点：
  209-210 °C
• 沸点：
  302.3±22.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 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：
  88.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  furan-2-carboxylic acid (4-nitrophenyl)amide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以95%的产率得到N-(4-氨基苯基)-2-糠酰胺
  参考文献：
  名称：

  Ligand efficiency based approach for efficient virtual screening of compound libraries

  摘要：

  Here we report for the first time the use of fit quality (FQ), a ligand efficiency (LE) based measure for virtual screening (VS) of compound libraries. The LE based VS protocol was used to screen an in-house database of 125,000 compounds to identify aurora kinase A inhibitors. First, 20 known aurora kinase inhibitors were docked to aurora kinase A crystal structure (PDB ID: 2W1C); and the conformations of docked ligand were used to create a pharmacophore (PH) model. The PH model was used to screen the database compounds, and rank (PH rank) them based on the predicted IC50 values. Next, LE_Scale, a weight-dependant LE function, was derived from 294 known aurora kinase inhibitors. Using the fit quality (FQ = LE/LE_Scale) score derived from the LE_Scale function, the database compounds were reranked (PH_FQ rank) and the top 151 (0.12% of database) compounds were assessed for aurora kinase A inhibition biochemically. This VS protocol led to the identification of 7 novel hits, with compound 5 showing aurora kinase A IC50 = 1.29 μM. Furthermore, testing of 5 against a panel of 31 kinase reveals that it is selective toward aurora kinase A & B, with <50% inhibition for other kinases at 10 μM concentrations and is a suitable candidate for further development. Incorporation of FQ score in the VS protocol not only helped identify a novel aurora kinase inhibitor, 5, but also increased the hit rate of the VS protocol by improving the enrichment factor (EF) for FQ based screening (EF = 828), compared to PH based screening (EF = 237) alone. The LE based VS protocol disclosed here could be applied to other targets for hit identification in an efficient manner.

  DOI：

  10.1016/j.ejmech.2014.06.029
• 作为产物：
  描述：

  糠酸（呋喃甲酸） 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 furan-2-carboxylic acid (4-nitrophenyl)amide
  参考文献：
  名称：

  噻吩和呋喃的芳香族化合物的核磁共振波谱分析法测定噻吩和呋喃的芳香指数

  摘要：

  一系列的米-和p -取代的苯甲酸，2-噻吩甲酸，和2-糠酸酰替苯胺的制备和它们的1 H和13 C NMR光谱特性进行了研究。通常，在酰基芳香环的质子和碳信号的化学位移与Hammettσ之间观察到良好的相关性。在二甲亚砜-d 6中，苯甲酰苯胺的羰基碳的化学位移值与2-硫代酰胺和2-呋喃酰胺的化学位移图具有极好的相关性，其斜率值分别为0.79和0.52 。该斜率可以被认为是一组芳香性指数。

  DOI：

  10.1002/jhet.5570390616

文献信息

• Jagodzinski, Tadeusz S.; Dziembowska, Teresa M.; Szczodrowska, Barbara, Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 5, p. 327 - 338
  作者：Jagodzinski, Tadeusz S.、Dziembowska, Teresa M.、Szczodrowska, Barbara

  DOI：——

  日期：——
• Farcasan; Makkay, Academia Republicii Populare Romine, Filiala Cluj, Studii si Cercetari de Chimie, 1957, vol. 8, p. 363,366
  作者：Farcasan、Makkay

  DOI：——

  日期：——
• Facile and Effective Synthesis of N-Aryl-2-Furancarboxamides Derivatives Under the Condition of Phase Transfer Catalysis
  作者：Tai-Bao Wei、You-Ming Zhang

  DOI：10.1080/00397919908086466

  日期：1999.9

  A convenient one-pot procedure is reported for the preparation of N-aryl-2-furancarboxamide derivatives. 2-Furoic acid is activated by benzenesulfonyl chloride under the condition of solid-liquid phase transfer catalysis using solid potassium carbonate as base and polyethylene glycol-400-(PEG-400) as phase transfer catalyst.
• JAGODZINSKI, TADEUSZ S.;DZIEMBOWSKA, TERESA M.;SZCZODROWSKA, BARBARA, BULL. SOC. CHIM. BELG., 98,(1989) N, C. 327-338
  作者：JAGODZINSKI, TADEUSZ S.、DZIEMBOWSKA, TERESA M.、SZCZODROWSKA, BARBARA

  DOI：——

  日期：——