4-chloro-N'-[(E)-(4-chloro-2-oxo-2H-chromen-3-yl)methylidene]benzohydrazide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-chloro-N'-[(E)-(4-chloro-2-oxo-2H-chromen-3-yl)methylidene]benzohydrazide
• 英文别名: 4-chloro-N′-[(E)-(4-chloro-2-oxo-2H-chromen-3-yl)methylidene]benzohydrazide；4-chloro-N-[(E)-(4-chloro-2-oxo-chromen-3-yl)methyleneamino]benzamide；4-chloro-N-[(E)-(4-chloro-2-oxochromen-3-yl)methylideneamino]benzamide
• 化学式: C₁₇H₁₀Cl₂N₂O₃
• 分子量: 361.184
• InChiKey: AXCOKGZIIPYZRO-AWQFTUOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 4-chloro-N'-[(E)-(4-chloro-2-oxo-2H-chromen-3-yl)methylidene]benzohydrazide
  参考文献：
  名称：

  2-芳酰基-[1]苯并吡喃并[4,3 - c ]吡唑-4（1H）-一衍生物及相关酰肼-azo的合成，抗菌作用及对接研究

  摘要：

  提出了一种新的方便的制备2-芳酰基-[1]苯并吡喃并[4,3 -c ]吡唑-4（1H）-一衍生物5b - g和含有酰肼-marin类似物4a - e的香豆素的简便方法。在体外测试了对参考菌株结核分枝杆菌H37Rv的抗分枝杆菌活性和对人胚胎肾细胞系HEK-293的细胞毒性。所有化合物均显示出0.28–1.69μM的显着最小抑菌浓度（MIC），与异烟肼相当。细胞毒性（IC 50 > 200 µM）相对于“正常细胞”模型HEK-293T表现出的2-芳酰基-[1]苯并吡喃并[4,3- -c ]吡唑-4（1 H）-one衍生物5b - e与类似物4a – e（IC 50 33–403 µM）。还对化合物4a – e和5b – g进行了分子对接研究，以研究它们与参与结核分枝杆菌的2-反式-烯酰-ACP还原酶（InhA）的结合细胞壁生物发生。结合模型表明，对于所有合成的化合物，或吡唑融合的香豆素衍生物与

  DOI：

  10.1016/j.bmcl.2017.05.011

文献信息

• In vitro and in silico evaluation of chromene based aroyl hydrazones as anticonvulsant agents
  作者：Violina T. Angelova、Yulian Voynikov、Pavlina Andreeva-Gateva、Slavina Surcheva、Nikolay Vassilev、Tania Pencheva、Jana Tchekalarova

  DOI：10.1007/s00044-017-1902-1

  日期：2017.9

  Series of aroyl hydrazones of 2H-chromene and coumarin carbaldehydes were synthesized and evaluated for their anticonvulsant activity and neurotoxicity. Further docking study on gamma-aminobutyric acid receptor was performed to elucidate their mechanisms of action. The highest protection was demonstrated by 2-furyl substituted 2H-chromene 8b in the maximal electroshock test (ED50 = 12.51 mg kg(-1), PI MES > 23.98) and the subcutaneous pentylenetetrazole tests (ED50 = 127.10 mg kg(-1)). Furyl-substituted derivative 4b (ED50 = 68.66 mg kg(-1)) was the most active in the maximal electroshock test while methoxyphenyl-substituted derivate 4c was the most active in the 6-Hz test (ED50 = 94.34 mg kg(-1)). None of the compounds displayed neurotoxicity in the rota-rod test. In silico assessment of their blood-brain barrier permeability indicated them as central nervous system active agents. The results suggest that coumarin/2H-chromene aroyl hydrazones scaffold deserve further evaluation in models of epilepsy and derivatization.