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.
• Synthesis, antimycobacterial activity and docking study of 2-aroyl-[1]benzopyrano[4,3- c ]pyrazol-4(1 H )-one derivatives and related hydrazide-hydrazones
  作者：Violina T. Angelova、Violeta Valcheva、Tania Pencheva、Yulian Voynikov、Nikolay Vassilev、Rositsa Mihaylova、Georgi Momekov、Boris Shivachev

  DOI：10.1016/j.bmcl.2017.05.011

  日期：2017.7

  isoniazid. The cytotoxicity (IC50 > 200 µM) to the “normal cell” model HEK-293T exhibited by 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives 5b–e, was noticeably milder compared to that of their hydrazone analogues 4a–e (IC50 33–403 µM). Molecular docking studies on compounds 4a–e and 5b–g were also carried out to investigate their binding to the 2-trans-enoyl-ACP reductase (InhA) enzyme involved

  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