4-[(1-Acetylindol-3-yl)methylidene]-2-phenyl-1,3-oxazol-5-one | 77362-24-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[(1-Acetylindol-3-yl)methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 77362-24-4
• 化学式: C₂₀H₁₄N₂O₃
• 分子量: 330.343
• InChiKey: SNVSWEBYYVWBGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  磺胺吡啶 、 4-[(1-Acetylindol-3-yl)methylidene]-2-phenyl-1,3-oxazol-5-one 在 sodium acetate 、 溶剂黄146 作用下， 以60%的产率得到4-[4-((1-acetyl-1H-indol-3-yl)methylene)-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl]-N-(pyridin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Inhibition studies on a panel of human carbonic anhydrases withN1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails

  摘要：

  Being the primary sulfonamide among the most efficient zinc binding group (ZBG) to design inhibitors for the metallo-enzymes carbonic anhydrases (CA, EC 4.2.1.1), herein, we propose an investigation on four physiologically important human (h) CAs (hCA I, II, IV, and IX) with N-1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails. The effect of the functionalisation of the sulfonamide group with five different substitution patterns, namely acetyl, pyridine, thiazole, pyrimidine, and carbamimidoyl, was evaluated in relation to the inhibition profile of the corresponding primary sulfonamide analogues. With most of these latter being nanomolar inhibitors of all four considered isoforms, a totally counterproductive effect on the inhibition potency can be ascribed to N-1-functionalisations of the ZBG primary sulfonamide structure with pyridine, thiazole, and pyrimidine moieties. On the other hand, incorporation of less hindered groups, such as sulfonylacetamides and sulfonylguanidines, maintained a certain degree of activity dependent on the tailing moiety, with K(I)s spanning in the low micromolar range.

  DOI：

  10.1080/14756366.2018.1446432
• 作为产物：
  描述：

  吲哚 在 sodium acetate 、 三氯氧磷 作用下， 生成 4-[(1-Acetylindol-3-yl)methylidene]-2-phenyl-1,3-oxazol-5-one
  参考文献：
  名称：

  Inhibition studies on a panel of human carbonic anhydrases withN1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails

  摘要：

  Being the primary sulfonamide among the most efficient zinc binding group (ZBG) to design inhibitors for the metallo-enzymes carbonic anhydrases (CA, EC 4.2.1.1), herein, we propose an investigation on four physiologically important human (h) CAs (hCA I, II, IV, and IX) with N-1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails. The effect of the functionalisation of the sulfonamide group with five different substitution patterns, namely acetyl, pyridine, thiazole, pyrimidine, and carbamimidoyl, was evaluated in relation to the inhibition profile of the corresponding primary sulfonamide analogues. With most of these latter being nanomolar inhibitors of all four considered isoforms, a totally counterproductive effect on the inhibition potency can be ascribed to N-1-functionalisations of the ZBG primary sulfonamide structure with pyridine, thiazole, and pyrimidine moieties. On the other hand, incorporation of less hindered groups, such as sulfonylacetamides and sulfonylguanidines, maintained a certain degree of activity dependent on the tailing moiety, with K(I)s spanning in the low micromolar range.

  DOI：

  10.1080/14756366.2018.1446432

文献信息

• Cascade reaction synthesis of multisubstituted bicyclic pyridone derivatives
  作者：Xuebing Chen、Dandan Zhu、Xiaoying Wang、Shengjiao Yan、Jun Lin

  DOI：10.1016/j.tet.2013.08.052

  日期：2013.11

  An efficient synthesis of novel bicyclic pyridone derivatives via cascade reaction of heterocyclic ketene aminals (HKAs) and 4-arylmethylene-2-phenyloxazol-5(4H)-ones in the presence of acetic acid has been established. Significantly, the protocol affords a straightforward approach to the construction of multisubstituted bicyclic pyridones in which one C–O bond was cleaved and new C–C and C–N bonds

  通过杂环烯酮缩胺的级联反应新的双环吡啶酮衍生物的有效合成（认可处）和4-芳亚甲基-2-苯基恶唑-5-（4 ħ） -酮在乙酸的存在已经建立。显著，该协议得到一简单的方法，其中一个C-O键裂解并形成新的C-C和C-N键以一锅煮的温和的条件下多取代的双环吡啶酮的结构。
• Inhibition studies on a panel of human carbonic anhydrases with<i>N</i>1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails
  作者：Fadi M. Awadallah、Silvia Bua、Walaa R. Mahmoud、Hossam H. Nada、Alessio Nocentini、Claudiu T. Supuran

  DOI：10.1080/14756366.2018.1446432

  日期：2018.1.1

  Being the primary sulfonamide among the most efficient zinc binding group (ZBG) to design inhibitors for the metallo-enzymes carbonic anhydrases (CA, EC 4.2.1.1), herein, we propose an investigation on four physiologically important human (h) CAs (hCA I, II, IV, and IX) with N-1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails. The effect of the functionalisation of the sulfonamide group with five different substitution patterns, namely acetyl, pyridine, thiazole, pyrimidine, and carbamimidoyl, was evaluated in relation to the inhibition profile of the corresponding primary sulfonamide analogues. With most of these latter being nanomolar inhibitors of all four considered isoforms, a totally counterproductive effect on the inhibition potency can be ascribed to N-1-functionalisations of the ZBG primary sulfonamide structure with pyridine, thiazole, and pyrimidine moieties. On the other hand, incorporation of less hindered groups, such as sulfonylacetamides and sulfonylguanidines, maintained a certain degree of activity dependent on the tailing moiety, with K(I)s spanning in the low micromolar range.