p-Hydroxy-benzaldehyd-cyanacetyl-hydrazon | 30010-06-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: p-Hydroxy-benzaldehyd-cyanacetyl-hydrazon
• 英文别名: 2-cyano-N-[(4-hydroxyphenyl)methylideneamino]acetamide
• CAS: 30010-06-1
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: BFGHGVRCXKFLGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  85.48
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  p-Hydroxy-benzaldehyd-cyanacetyl-hydrazon 、 对二甲氨基苯甲醛 在 吡啶 作用下， 以 乙醇 为溶剂， 以60%的产率得到N'-(4-hydroxy-benzylidene)-2-cyano-3-(4-dimethylaminophenyl)acrylohydrazide
  参考文献：
  名称：

  Microwave Assisted Synthesis and Evaluation of N-Cinnamoyl Aryl Hydrazones for Cytotoxic and Antioxidant Activities

  摘要：

  A series of N-cinnamoyl aryl hydrazones 2a-2i were synthesized in good yields by microwave irradiation technique. The title compounds were formed by nucleophilic condensation of various N-1-substituted benzylidene-2-cyano aceto hydrazides with N,N-dimethyl amino benzaldehyde. The intermediate N-1-substituted benzylidene-2-cyano aceto hydrazide was obtained by condensing various substituted benzaldehydes with cyanoacetohydrazide. The structures of the compounds were characterized by IR, H-1 NMR and Mass spectra. The antioxidant activity was studied by reduction of DPPH, scavenging of nitric oxide and hydrogen peroxide methods with ascorbic acid as the standard drug. The compounds were evaluated for cytotoxic activity by BSLT method and their ED50 values were compared the standard podophyllotoxin. Among the compounds evaluated, N-1-benzylidene-2-cyano-3-(4-dimethylamino) phenyl acrylo hydrazide (2a) and N-1-(4-methoxy-benzylidene)-2-cyano3-(4-dimethylamino) phenyl acrylohydrazide (2e) showed good antioxidant activity towards all the three models. The compounds 2a and 2e showed ED50 values 3.07 mu g/ml and 3.7 mu g/ml respectively which were compared against the standard podophyllotoxin (1.64 mu g/ml).

  DOI：

  10.13005/ojc/320350
• 作为产物：
  描述：

  对羟基苯甲醛 在 哌啶 、 己酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 p-Hydroxy-benzaldehyd-cyanacetyl-hydrazon
  参考文献：
  名称：

  Alonso, Paloma; Martin-Leon, Nazario; Quinteiro, Margarita, Liebigs Annalen der Chemie, 1990, # 9, p. 841 - 846

  摘要：

  DOI：

文献信息

• 7‐Amino‐2‐aryl/hetero‐aryl‐5‐oxo‐5,8‐dihydro[1,2,4]triazolo[1,5‐<i>a</i>]pyridine‐6‐carbonitriles: Synthesis and adenosine receptor binding studies
  作者：Khasim Shaik、Pran Kishore Deb、Raghu Prasad Mailavaram、Balakumar Chandrasekaran、Sonja Kachler、Karl‐Norbert Klotz、Abdul Muttaleb Yousef Jaber

  DOI：10.1111/cbdd.13528

  日期：——

  A series of novel 7‐amino‐5‐oxo‐2‐substituted‐aryl/hetero‐aryl‐5,8‐dihydro[1,2,4]triazolo[1,5‐a]pyridine‐6‐carbonitriles (4a–4t) was synthesized, characterized and evaluated for their binding affinity and selectivity towards hA1, hA2A, hA2B and hA3 adenosine receptors (ARs). Compound 4a with a phenyl ring at 2‐position of the triazolo moiety of the scaffold showed high affinity and selectivity for

  一系列新颖的7-氨基-5-氧代-2-取代的芳基/杂芳基-5,8-二氢[1,2,4]三唑[1,5 - a ]吡啶-6-腈（4a– 4吨）合成，其特征在于，评价向HA的结合亲和力和选择性1，HA 2A，HA 2B和HA 3腺苷受体（ARS）。在支架的三唑部分的2位带有苯环的化合物4a对hA 1 AR（K i hA 1  = 0.076μM，hA 2A  = 25.6μM和hA 3）具有高亲和力和选择性 > 100μM）。在苯环的不同位置引入各种给电子和吸电子基团，导致对所有AR的亲和力和选择性大大降低，除了在2位带有4-羟基苯基的化合物4b。有趣的是，用较小的杂环噻吩环取代苯环（π过量的体系）导致对化合物4t的hA 1 AR的亲和力进一步提高（K i hA 1  = 0.051μM，hA 2A  = 9.01μM和hA 3  > 13.9μM），同时保留了对所有其他类似于化合物4a的AR亚型的
• Synthese einiger Cyanessigsäurehydrazidderivate. 7. Mitteilung über Synthese tuberkulostatischer Substanzen
  作者：Josef Klosa

  DOI：10.1002/ardp.19552881004

  日期：——