4-[2-(Dicyanomethylidene)hydrazinyl]benzoic acid | 55653-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[2-(Dicyanomethylidene)hydrazinyl]benzoic acid
• CAS: 55653-17-3
• 化学式: C₁₀H₆N₄O₂
• mdl: MFCD00459446
• 分子量: 214.183
• InChiKey: YIVFVVDFGWXSHG-UHFFFAOYSA-N

物化性质

• 熔点：
  260 °C
• 沸点：
  409.5±47.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[2-(Dicyanomethylidene)hydrazinyl]benzoic acid 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 3,5-diamino-4-(4-carboxy)phenylazo-pyrazole
  参考文献：
  名称：

  4-Arylazo-3,5-diamino-1H-pyrazole CDK Inhibitors:  SAR Study, Crystal Structure in Complex with CDK2, Selectivity, and Cellular Effects

  摘要：

  In a routine screening of our small-molecule compound collection we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of ATP antagonists with moderate potency against CDK2-cyclin E. A preliminary SAR study based on 35 analogues suggests ways in which the pharmacophore could be further optimized, for example, via substitutions in the 4-aryl ring. Enzyme kinetics studies with the lead compound and X-ray crystallography of an inhibitor-CDK2 complex demonstrated that its mode of inhibition is competitive. Functional kinase assays confirmed the selectivity toward CDKs, with a preference for CDK9cyclin T1. The most potent inhibitor, 4-[(3,5-diamino-1H-pyrazol-4-yl) diazenyl] phenol 31b (CAN508), reduced the frequency of S-phase cells of the cancer cell line HT-29 in antiproliferation assays. Further observed cellular effects included decreased phosphorylation of the retinoblastoma protein and the C-terminal domain of RNA polymerase II, inhibition of mRNA synthesis, and induction of the tumor suppressor protein p53, all of which are consistent with inhibition of CDK9.

  DOI：

  10.1021/jm0605740
• 作为产物：
  描述：

  培美曲塞二钠杂质14 、 丙二腈 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 以87%的产率得到4-[2-(Dicyanomethylidene)hydrazinyl]benzoic acid
  参考文献：
  名称：

  On the Chemistry of Cinnoline I. Synthesis and Reactions of (4-Amino-cinnolin-3-yl)-p-tolyl-methanones

  摘要：

  The synthesis of a series of (4-Amino-cinnolin-3-yl)-p-tolyl-methanones from aryl-hydrazonomalononitrile in a one step procedure is reported. The (4-amino-cinnolin-3-yl)-p-tolyl- methanones could be annelated to the corresponding 1,2-dihydro-4-(p-tolyl)-2-oxopyrido[3,2-c]cinnoline derivatives via (4-acetamido-cinnolin-3-yl)-p-tolyl-methanones. Treatment of 1,2-dihydro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline-2-one with POCl3 and P2S5 gave 2-chloro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline. and 1,2-dihydro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline-2-thione. Treatment of the ketone with malononitrile afforded 2-amino-3-cyano-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline. Using these ketones, a facile and convenient route towards substituted pyrimidino[5,4-c]-cinnolines was developed. Chemical and spectroscopic evidences for the structures of the new compounds are presented.

  DOI：

  10.1007/pl00010201