2-(p-fluorophenyldiazo)malononitrile

• 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: 2-(p-fluorophenyldiazo)malononitrile
• 英文别名: 2-[(4-Fluorophenyl)diazenyl]propanedinitrile；2-[(4-fluorophenyl)diazenyl]propanedinitrile
• 化学式: C₉H₅FN₄
• 分子量: 188.164
• InChiKey: QNKWUOMZLCUTQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(p-fluorophenyldiazo)malononitrile 在 hydrazine hydrate 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2,5-diamino-3-((4-fluorophenyl)diazenyl)-7-(p-tolyl)pyrazolo[1,5-a]pyrimidine-6-carbonitrile
  参考文献：
  名称：

  新型吡唑并[1,5-a]嘧啶PIM激酶抑制剂和凋亡诱导剂的设计、合成、生物学评价及分子对接研究

  摘要：

  本研究涉及设计并合成吡唑并[1,5- a ]嘧啶5a-l的新衍生物，该衍生物是通过4-Arylazo-1H-吡唑-3,5-二胺3a,b与亚芳基丙二腈（4a- f ) 在回流甲醇中。使用不同的光谱技术确认了合成衍生物的结构。利用目标吡唑并[1,5- a ]嘧啶5j与PIM-1酶的活性结合位点之间的对接模拟，实现了新设计的衍生物的虚拟筛选。新型吡唑并衍生物的细胞毒性[1,5- a]嘧啶框架在癌细胞系上进行筛选：结肠癌细胞系（HCT-116）、肝细胞癌细胞系（Hep-G2）和乳腺癌细胞系（MCF-7）。与阿霉素相比，化合物2,5-二氨基-7-(4-乙氧基苯基)-3-(对甲苯基二氮烯基)吡唑并[1,5-a]嘧啶-6-甲腈； 5h，2，5-二氨基-7-(4-羟基-3-甲氧基苯基)-3-(对甲苯基二氮烯基)吡唑并[1，5-a]嘧啶-6-甲腈；5j，和2，5-二氨基-7-(呋喃-2-基)-3-(对甲苯基

  DOI：

  10.1016/j.molstruc.2023.136811
• 作为产物：
  描述：

  4-氟苯胺 、 丙二腈 在 对甲苯磺酸 、 sodium nitrite 作用下， 反应 0.07h， 以92%的产率得到2-(p-fluorophenyldiazo)malononitrile
  参考文献：
  名称：

  4-Fluorophenylhydrazones as potential COX-2 inhibitors: a novel, efficient, one pot solid phase synthesis, docking study and pharmacological evaluation

  摘要：

  In search of a new class of organic compounds as potential COX-2 inhibitors, various 4-Fluorophenylhydrazones (3a-3i) have been synthesized and molecular docking study was conducted. All the synthesized compounds were also evaluated for their in vivo anti-inflammatory potential using carrageenan-induced rat paw odema method. In the present manuscript, a novel, simple, and greener protocol has been developed for the first time to prepare the hydrazo compounds by a one pot solid phase reaction between various active methylene compounds and p-fluoroaniline in the presence of p-toluene sulfonic acid as a new solid phase organocatalyst. The catalyst dramatically facilitates the reaction under solvent-free condition at moderate temperature (10-15 A degrees C). The present protocol not only provides an expeditious route to prepare hydrazo compounds in excellent yields (with in 3-5 min) but also avoids the use of two step conventional methods, and formation of side products. The results obtained from in vivo anti-inflammatory activity through carrageenan-induced rat paw odema assay showed that compounds 3a-3b, and 3d displayed excellent level of activity which was further supported by molecular docking study. A cyclooxygenase-II inhibitory molecular docking study has been carried out using (pdb: 1CX2) via Molegro Virtual Docker version 4.2.1. All the compounds were found to exhibit good level of inhibition and binding in the enzyme active site. Compounds 3a-3b, 3d, and 3e have been found to display high moldock scores -118.333, -118.778, -118.422, and -111.13, respectively, and are strongly bound with Arg120, Tyr355, His90, and Arg513 amino acids, which are responsible for COX-2 inhibition within the active site. In the present investigation, it can be concluded that the best scored inhibitors with good in vivo anti-inflammtory activity will have better chances to be used as anti-inflammatory leads.

  DOI：

  10.1007/s00044-013-0566-8

文献信息

• Design and synthesis of Novel 3,5-Diamino-4-(2′,3′,4′-Substituted Phenylazo)-1–2,5-dichlorphenylpyrazoles: Unveiling dual proficiency against inflammation and bacteria
  作者：Ketan Vashisht、Pooja Sethi、Anshul Bansal、Sumeet Gupta、Mohammad Ovais Dar、Ahmad Umar、Raman Kumar、Sushil Kumar、Hitesh Kumar、Abdulrab Ahmed M. Alkhanjaf、Ahmed A. Ibrahim、Sotirios Baskoutas

  DOI：10.1016/j.molstruc.2024.139109

  日期：2024.12

  This study introduces a novel series of 3,5-diamino-4-(2′,3′,4′-substitued phenylazo)-1–2,5-dicholorphenylpyrazole derivatives, synthesized through nucleophilic substitution reactions between 2-[(substituted phenyl) hydrazono] malononitrile and 2,5-dichlorophenyl hydrazine under reflux conditions in an ethanolic medium. These compounds exhibit potent antibacterial and anti-inflammatory properties,

  本研究介绍了一系列新颖的3,5-二氨基-4-(2′,3′,4′-取代的苯基偶氮)-1–2,5-二氯苯基吡唑衍生物，这些衍生物是通过2-[(取代的苯基)之间的亲核取代反应合成的)亚肼基]丙二腈和2,5-二氯苯肼在乙醇介质中回流条件下。通过体外测定和分子对接研究证明，这些化合物具有有效的抗菌和抗炎特性。合成的吡唑结构的独特性有助于其双重能力，标志着有机化学领域的重大进步。使用IR、H、C NMR 和质谱分析完成了合成衍生物的结构表征。对新合成的取代吡唑的抗菌（体外）和抗炎（体内）潜力进行了系统评估。角叉菜胶诱导的炎症抑制在化合物 4 小时中尤为突出，表现出显着的抗炎活性。针对四种细菌菌株进行了体外抗菌测定，包括（MTCC 121）、（MTCC 96）、（MTCC 1652）和（MTCC 741）。合成的吡唑衍生物对革兰氏阳性和革兰氏阴性菌株均表现出中等至优异的抗菌活性。化合物 4 g 显示出最高的抑制区，最低抑制浓度