5-Oxo-3-phenyl-Δ²-pyrazolin-4-aldehyd | 90771-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 5-Oxo-3-phenyl-Δ²-pyrazolin-4-aldehyd
• 英文别名: 3-oxo-5-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde；5-oxo-3-phenyl-4,5-dihydro-1H-pyrazole-4-carbaldehyde；5-Oxo-3-phenyl-4,5-dihydro-1H-pyrazol-4-carbaldehyd；5-Oxo-3-phenyl-1,4-dihydropyrazole-4-carbaldehyde
• CAS: 90771-00-9
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: NWQWEGNTUMEQLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Oxo-3-phenyl-Δ²-pyrazolin-4-aldehyd 、 3-氨基-5-(2-呋喃基)吡唑 在 对甲苯磺酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以56%的产率得到
  参考文献：
  名称：

  Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones

  摘要：

  Twenty five 4-aminomethylidene derivatives obtained from 3-phenyl-2-pyrazolin-5-one and 1,3-diphenyl-2-pyrazolin-5-one were synthesized and tested for their antiproliferative activity against human breast cancer MDA-MB-361 and MDA-MB-453 cell lines. The compounds derived from 1,3-diphenyl-2-pyrazolin-5-one exhibited the most remarkable activity in the treatment of both cell lines. In vitro antiproliferative activities were accompanied by an important apoptotic fraction of both cell lines; also, compounds inhibited key endothelial cell functions implicated in invasion and angiogenesis. QSAR methods were performed in order to analyze the influence of structural features of the compounds investigated on the antiproliferative potential on MDA-MB-361 and MDA-MB-453 cancer cells. One-parameter heuristic analysis was performed and different whole molecule and fragmental descriptors were considered for rationalization of mechanism of interaction of these compounds with active place of hypothetical target included in tumorigenesis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.025
• 作为产物：
  描述：

  苯甲酰乙酸甲酯 在 肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 4.5h， 生成 5-Oxo-3-phenyl-Δ²-pyrazolin-4-aldehyd
  参考文献：
  名称：

  Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones

  摘要：

  Twenty five 4-aminomethylidene derivatives obtained from 3-phenyl-2-pyrazolin-5-one and 1,3-diphenyl-2-pyrazolin-5-one were synthesized and tested for their antiproliferative activity against human breast cancer MDA-MB-361 and MDA-MB-453 cell lines. The compounds derived from 1,3-diphenyl-2-pyrazolin-5-one exhibited the most remarkable activity in the treatment of both cell lines. In vitro antiproliferative activities were accompanied by an important apoptotic fraction of both cell lines; also, compounds inhibited key endothelial cell functions implicated in invasion and angiogenesis. QSAR methods were performed in order to analyze the influence of structural features of the compounds investigated on the antiproliferative potential on MDA-MB-361 and MDA-MB-453 cancer cells. One-parameter heuristic analysis was performed and different whole molecule and fragmental descriptors were considered for rationalization of mechanism of interaction of these compounds with active place of hypothetical target included in tumorigenesis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.025

文献信息

• Rapid and Efficient Synthesis of 4-Substituted Pyrazol-5-one under Microwave Irradiation in Solvent-Free Conditions
  作者：Magdy A.-H. Zahran、Farag A-A. El-Essawy、Salah M. Yassin、Tarek A-R. Salem、Nader M. Boshta

  DOI：10.1002/ardp.200700121

  日期：2007.11

  New heterocyclic compounds containing pyrazol‐5‐one coupled with benzimidazole, benzothiazole, benzoxazole, quinoline, naphthyridin, and pyrazole were synthesized. Comparative investigations to synthesize these interesting classes of heterocyclic compounds through conventional heating or under microwave‐irradiation conditions were presented. Synthesized compounds 1a, 2a, 4k, 3a, c, 5a, b, 6b, 7a, b

  合成了含有吡唑-5-的新型杂环化合物与苯并咪唑、苯并噻唑、苯并恶唑、喹啉、萘啶和吡唑偶联。介绍了通过常规加热或在微波辐射条件下合成这些有趣类别的杂环化合物的比较研究。对合成的化合物 1a、2a、4k、3a、c、5a、b、6b、7a、b、d、8a 和 9a 的抗肿瘤活性进行了评估。这些化合物中的一些表现出有希望的抗肿瘤活性。
• Ridi, Gazzetta Chimica Italiana, 1952, vol. 82, p. 746,753
  作者：Ridi

  DOI：——

  日期：——