AG 775 | 134604-46-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酰胺
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: AG 775
• 英文别名: 2-cyano-3-(3,4,5-trihydroxy-phenyl)-acrylic acid amide；2-Cyan-3-(3,4,5-trihydroxy-phenyl)-acrylsaeure-amid；3.4.5-Trioxy-benzylidencyanacetamid；(E)-2-cyano-3-(3,4,5-trihydroxyphenyl)prop-2-enamide
• CAS: 134604-46-9
• 化学式: C₁₀H₈N₂O₄
• 分子量: 220.185
• InChiKey: IZDSLPGXLRWXIF-LZCJLJQNSA-N

物化性质

• 沸点：
  629.5±55.0 °C(Predicted)
• 密度：
  1.616±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  AG 775 、 乙酸酐 在 吡啶 作用下， 生成 2-cyano-3-(3,4,5-triacetoxy-phenyl)-acrylic acid amide
  参考文献：
  名称：

  Rosenmund; Boehm, Justus Liebigs Annalen der Chemie, 1924, vol. 437, p. 143

  摘要：

  DOI：
• 作为产物：
  描述：

  酪氨酸磷酸化抑制剂25 在 盐酸 作用下， 生成 AG 775
  参考文献：
  名称：

  Rosenmund; Boehm, Justus Liebigs Annalen der Chemie, 1924, vol. 437, p. 143

  摘要：

  DOI：

文献信息

• Polyhydroxylated Phenylacrylic Acid Derivatives as New Anti-tumor Agents
  作者：Sajjat Hussoin、George B. FitzGerald、Michael M. Wick

  DOI：10.1002/jps.2600800503

  日期：1991.5

  Preliminary evidence indicates that antitumor agents containing the o-dihydroxybenzene moiety exhibit enhanced antitumor activity toward malignant cells of high oxidative potential, such as melanoma cells. Based on this consideration, 11 hydroxybenzene acrylic acid derivatives of differing redox potential were prepared as potential substrates for the melanoma specific enzyme tyrosinase, that might

  初步证据表明，含有邻二羟基苯部分的抗肿瘤药对黑色素瘤细胞等具有高氧化潜能的恶性细胞表现出增强的抗肿瘤活性。基于此考虑，制备了具有不同氧化还原电势的11种羟苯丙烯酸衍生物作为黑素瘤特异性酶酪氨酸酶的潜在底物，其可能表现出一般的抗肿瘤活性并增强了对黑素瘤细胞的细胞毒性。这些化合物中的五个[α-氰基-β-（4-羟基苯基）-，α-氰基-β-（3,4-二羟基苯基）-和α-氰基-β-（3,4,5-三羟基苯基）丙烯酸发现酪氨酸酶（THPPA）和3,4-二羟基-和3,4,5-三羟基苯并氰基乙酰胺]是酪氨酸酶的底物，Km值为0.08至4.13 mM，Vmax值为0.18至3.02。这些数据表明，随着羟基数目的增加，氧化速率增加，并且氰酰胺比相应的氰酸的反应更快，其中二氰化物的反应性最低。相反，氰酰胺作为底物的效果不如氰酸。体外研究表明，除两种化合物外，所有化合物均对L1210（IC50范围为21-980 m
• 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：——
• Rosenmund; Boehm, Justus Liebigs Annalen der Chemie, 1924, vol. 437, p. 143
  作者：Rosenmund、Boehm

  DOI：——

  日期：——