1-acetyl-3-(4-bromophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole | 313670-86-9

• 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: 1-acetyl-3-(4-bromophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole
• 英文别名: 1-(3-(4-bromophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethanone；1-[5-(4-bromophenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 313670-86-9
• 化学式: C₁₇H₁₅BrN₂O
• 分子量: 343.223
• InChiKey: NDDVKHTZDIXGBF-UHFFFAOYSA-N

物化性质

• 沸点：
  448.6±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-acetyl-3-(4-bromophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole 、 水杨醛 、 丙二腈 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以77%的产率得到2-amino-6-[3-(4-bromophenyl)-5-phenyl-4,5-dihydropyrazol-1-yl]-4-(2-hydroxyphenyl)nicotinonitrile
  参考文献：
  名称：

  Anticonvulsant Activity of a Combined Pharmacophore of Pyrazolo-pyridines with Lesser Toxicity in Mice

  摘要：

  设计并合成了多种2-氨基-6-[3-(取代苯基)-5-苯基-4,5-二氢吡唑-1-基]-4-(取代苯基)氮杂喹啉腌酸盐（3a-t），通过组合两种活性抗癫痫药物结构单元吡唑和吡啶。所有合成的化合物都具备良好抗癫痫活性所需的药效团元素。抗癫痫筛选通过最大电震抽搐（MES）和皮下戊二脳（scPTZ）测试进行。化合物3i和3s在这两项筛选中均显示出显著的抗癫痫活性，其在MES筛选中的$ED_{50}$值分别为17.5 mg/kg和22.6 mg/kg，在scPTZ筛选中分别为154.1 mg/kg和242.6 mg/kg。在较高剂量下测试时，它们在小鼠中也未显示出急性毒性效果。

  DOI：

  10.5012/bkcs.2011.32.2.576
• 作为产物：
  描述：

  4-溴苯乙酮 在 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.5h， 生成 1-acetyl-3-(4-bromophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole
  参考文献：
  名称：

  Anticonvulsant Activity of a Combined Pharmacophore of Pyrazolo-pyridines with Lesser Toxicity in Mice

  摘要：

  设计并合成了多种2-氨基-6-[3-(取代苯基)-5-苯基-4,5-二氢吡唑-1-基]-4-(取代苯基)氮杂喹啉腌酸盐（3a-t），通过组合两种活性抗癫痫药物结构单元吡唑和吡啶。所有合成的化合物都具备良好抗癫痫活性所需的药效团元素。抗癫痫筛选通过最大电震抽搐（MES）和皮下戊二脳（scPTZ）测试进行。化合物3i和3s在这两项筛选中均显示出显著的抗癫痫活性，其在MES筛选中的$ED_{50}$值分别为17.5 mg/kg和22.6 mg/kg，在scPTZ筛选中分别为154.1 mg/kg和242.6 mg/kg。在较高剂量下测试时，它们在小鼠中也未显示出急性毒性效果。

  DOI：

  10.5012/bkcs.2011.32.2.576

文献信息

• A rational approach for the design and synthesis of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles as a new class of potential non-purine xanthine oxidase inhibitors
  作者：Kunal Nepali、Gurinderdeep Singh、Anil Turan、Amit Agarwal、Sameer Sapra、Raj Kumar、Uttam C. Banerjee、Prabhakar K. Verma、Naresh K. Satti、Manish K. Gupta、Om P. Suri、K.L. Dhar

  DOI：10.1016/j.bmc.2011.01.058

  日期：2011.3

  Xanthine oxidase is a complex molybdoflavoprotein that catalyses the hydroxylation of xanthine to uric acid. Fifty three analogues of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles were rationally designed and synthesized and evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Some notions about structure activity relationships are presented. Six compounds 41, 42, 44, 46,

  黄嘌呤氧化酶是一种复杂的钼黄素蛋白，可催化黄嘌呤羟化为尿酸。合理设计和合成了1-乙酰基3,5-二芳基-4,5-二氢（1 H）吡唑的53种类似物，并首次评估了其体外黄嘌呤氧化酶抑制活性。提出了有关结构活动关系的一些概念。六种化合物41，42，44，46，55和59被认为是最有效对抗XO带IC 50范围为5.3μM至15.2μM。化合物59成为最有效的XO抑制剂（IC 50 = 5.3μM）。通过分子模拟已经确定了59与XO活性位点氨基酸残基的一些重要相互作用。
• Design, synthesis, and structure–activity relationships of pyrazole derivatives as potential FabH inhibitors
  作者：Peng-Cheng Lv、Juan Sun、Yin Luo、Ying Yang、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2010.05.105

  日期：2010.8

  Fatty acid biosynthesis is essential for bacterial survival. FabH, beta-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and - \negative bacteria. Fifty-six 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives were synthesized and developed as potent inhibitors of FabH. This inhibitor class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 1-(5-(4-fluorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl) ethanone (12) and 1-(5-(4-chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl) ethanone (13) were potent inhibitors of E. coli FabH. (C) 2010 Elsevier Ltd. All rights reserved.
• Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones
  作者：Kunal Nepali、Kanika Kadian、Ritu Ojha、Rajni Dhiman、Atul Garg、Gagandip Singh、Abhishek Buddhiraja、Preet Mohinder Singh Bedi、Kanaya Lal Dhar

  DOI：10.1007/s00044-011-9824-9

  日期：2012.10

  Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C-6-C-3-C-6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines.All the synthesized compounds were evaluated for in vitro cytotoxicity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Compound 68 was found to be the most potent showing broad spectrum of cytotoxicity against all the cell lines .