3-carbamoyl-6-hydroxy-2-iminochromene

• 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: 3-carbamoyl-6-hydroxy-2-iminochromene
• 英文别名: 6-Hydroxy-2-imino-2H-chromene-3-carboxylic acid amide；6-hydroxy-2-iminochromene-3-carboxamide
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: WGTXGYFYUFECCA-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：

  3-carbamoyl-6-hydroxy-2-iminochromene 以 氘代二甲亚砜 为溶剂， 生成 2,5-dihydroxy-α-cyanocinnamamide
  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：

  2,4-二羟基苯甲醛 以93%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

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

  DOI：——

  日期：——
• 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
  作者：O'Callaghan, Conor N.、McMurry, T. Brian H.、O'Brien, John E.

  DOI：——

  日期：——