3-carbamoyl-7-hydroxy-2-iminochromene | 71586-40-8

• 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-7-hydroxy-2-iminochromene
• 英文别名: 7-hydroxy-2-imino-2H-chromene-3-carboxamide；7-hydroxy-2-iminochromene-3-carboxamide
• CAS: 71586-40-8
• 化学式: C₁₀H₈N₂O₃
• mdl: MFCD00227487
• 分子量: 204.185
• InChiKey: HUDOTUMVHSZQHK-UHFFFAOYSA-N

物化性质

• 沸点：
  479.7±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

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-7-hydroxy-2-iminochromene 生成 2-Amino-3-carbamoyl-7-hydroxy-chromenylium; perchlorate
  参考文献：
  名称：

  Rubtsov, M. I.; Lukatskaya, L. L.; Karasev, A. A., Russian Journal of General Chemistry, 1999, vol. 69, # 1, p. 134 - 137

  摘要：

  DOI：
• 作为产物：
  描述：

  氰乙酰胺 、 2,4-二羟基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以93%的产率得到3-carbamoyl-7-hydroxy-2-iminochromene
  参考文献：
  名称：

  Bicyclic compounds as ring-constrained inhibitors of protein-tyrosine kinase p56lck

  摘要：

  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.

  DOI：

  10.1021/jm00056a001

文献信息

• Reactions of 5-diazoimidazoles with steroid hydrazones
  作者：E. V. Sadchikova、E. A. Kureneva、E. A. Shtokareva、I. S. Selezneva

  DOI：10.1007/s10593-005-0071-1

  日期：2004.11
• Recyclization of 2-imino-2H-1-benzopyrans under the influence of nucleophilic reagents. 2. Reaction of 2-iminocoumarin-3-carboxamides witho-aminobenzenesulfonamide
  作者：S. N. Kovalenko、V. P. Chernykh、A. E. Shkarlat、I. V. Ukrainets、V. I. Gridasov、S. A. Rudnev

  DOI：10.1007/bf02251684

  日期：1998.7
• 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：——
• New derivatives of coumarin: 2-(N-R-imino)-2H-1-benzopyrans
  作者：V. A. Zubkov、S. N. Kovalenko、V. P. Chernykh、S. M. Ivkov

  DOI：10.1007/bf01166306

  日期：1994.6