8-hydroxy-2-imino-2H-chromene-3-carboxamide | 146515-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-hydroxy-2-imino-2H-chromene-3-carboxamide
• 英文别名: 8-hydroxy-2-iminochromene-3-carboxamide
• CAS: 146515-48-2
• 化学式: C₁₀H₈N₂O₃
• mdl: MFCD04240939
• 分子量: 204.185
• InChiKey: OVERVMFXBXLJBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-hydroxy-2-imino-2H-chromene-3-carboxamide 以 氘代二甲亚砜 为溶剂， 生成 (E)-2-Cyano-3-(2,3-dihydroxy-phenyl)-acrylamide
  参考文献：
  名称：

  O'Callaghan, Conor N.; McMurry, T. Brian H.; O'Brien, John E., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 2, p. 425 - 429

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二羟基苯甲醛 以29%的产率得到
  参考文献：
  名称：

  Burke (Jr) Terrence R., Lim Benjamin, Marquez Victor E., Li Zhen-Hong, Bo+, J. Med. Chem., 36 (1993) N 4, S 425-432

  摘要：

  DOI：

文献信息

• Recyclization of 2-Imino-2<i>H</i>-1-benzopyrans with Nucleophilic Reagents - Reaction of 2-Iminocoumarin-3-carboxamides with 2-Aminothiophene-3-carboxamides
  作者：Sergiy M. Kovalenko、Sergiy V. Vlasov、Valentin P. Chernykh

  DOI：10.1055/s-2006-926333

  日期：——

  In the course of our research on the synthesis of coumarins, the interaction of 2-iminocoumarin-3-carboxamides with a series of 2-aminothiophene-3-carboxamides was studied. It was established that the initial products - 2-substituted coumarin-3-carboxamides - can undergo rearrangement to 2-(coumarin-3-yl)thieno[2,3-d]pyrimidin-4-ones by refluxing in DMF.

  在我们合成香豆素的研究过程中，研究了 2-亚氨基香豆素-3-羧酰胺与一系列 2-氨基噻吩-3-羧酰胺的相互作用。已确定初始产物 - 2-取代香豆素-3-羧酰胺 - 通过在 DMF 中回流可以重排为 2-(香豆素-3-基)噻吩并[2,3-d]嘧啶-4-酮。
• Bicyclic compounds as ring-constrained inhibitors of protein-tyrosine kinase p56lck
  作者：Terrence R. Burke、Benjamin Lim、Victor E. Marquez、Zhen Hong Li、Joseph B. Bolen、Irena Stefanova、Ivan D. Horak

  DOI：10.1021/jm00056a001

  日期：1993.2

  A study was undertaken to prepare inhibitors of the lymphocyte protein-tyrosine kinase p56lck. Using the known p56lck inhibitor 3,4-dihydroxy-alpha-cyanocinnamamide (4) as a lead compound, bicyclic analogues were designed as conformationally constrained mimetics in which the phenyl ring and vinyl side chain of the cinnamamide are locked into a coplanar orientation. Such planarity was rationalized to be an important determinant for binding within a putative flat, cleftlike catalytic cavity. Bicyclic analogues were prepared using the naphthalene, quinoline, isoquinoline, and 2-iminochromene ring systems and examined for their ability to inhibit autophosphorylation of immunopurified p56lck. The most potent analogues were methyl 7,8-dihydroxyisoquinoline-3-carboxylate (12) (IC50 = 0.2 muM) and 7,8-dihydroxyisoquinoline-3-carboxamide (13) (IC50 = 0.5 muM). Inhibition by 12 was not competitive with respect to ATP. These compounds may represent important new structural motifs for the development of p56lck inhibitors.