2-(3,5-dimethyl-1H-pyrazol-1-yl)-1-(4-nitrophenyl)ethanone | 890640-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3,5-dimethyl-1H-pyrazol-1-yl)-1-(4-nitrophenyl)ethanone
• 英文别名: 2-(3,5-Dimethylpyrazol-1-yl)-1-(4-nitrophenyl)ethanone
• CAS: 890640-99-0
• 化学式: C₁₃H₁₃N₃O₃
• 分子量: 259.265
• InChiKey: BWEMHUTYCTVWNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethyl-1H-pyrazol-1-yl)-1-(4-nitrophenyl)ethanone 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 以34%的产率得到2-(3,5-dimethyl-1H-pyrazol-1-yl)-4-nitroacetophenone oxime
  参考文献：
  名称：

  Synthesis, structural and pharmacological exploration of 2-(3, 5-dimethyl-1H-pyrazol-1-yl)-acetophenone oximes and their silver complexes

  摘要：

  DOI：

  10.1016/j.poly.2020.114972
• 作为产物：
  描述：

  3,5-二甲基吡唑 、 2-溴-4'-硝基苯乙酮 在 sodium carbonate 作用下， 反应 0.33h， 生成 2-(3,5-dimethyl-1H-pyrazol-1-yl)-1-(4-nitrophenyl)ethanone
  参考文献：
  名称：

  Synthesis, structural and pharmacological exploration of 2-(3, 5-dimethyl-1H-pyrazol-1-yl)-acetophenone oximes and their silver complexes

  摘要：

  DOI：

  10.1016/j.poly.2020.114972

文献信息

• One-pot synthesis of trisubstituted pyrazoles via multicomponent approach
  作者：P. Santhosh、V. S. R. Chunduru、V. Rajeswar Rao

  DOI：10.1007/s10593-011-0779-z

  日期：2011.7

  An efficient one-pot multicomponent reaction for the synthesis of 1-aryl- or 1-heteryl-substituted 3,5-dimethylpyrazoles with excellent yields has been described. Reaction of 3-(2-bromoacetyl)coumarins or phenacyl bromides with acetylacetone and hydrazine hydrate in ethanol afforded the corresponding 3,5-dimethylpyrazoles in good yields. All the synthesized compounds were characterized by their analytical

  已经描述了以优异的产率合成1-芳基-或1-杂基-取代的3，5-二甲基吡唑的有效的一锅多组分反应。3-（2-溴乙酰基）香豆素或苯甲酰溴与乙酰丙酮和肼水合物在乙醇中的反应以良好的产率得到了相应的3,5-二甲基吡唑。所有合成的化合物均以其分析和光谱数据为特征。
• Synthesis and biological evaluation of some 2-(3,5-dimethyl-1H-pyrazol-1-yl)-1-arylethanones: Antibacterial, DNA photocleavage, and anticancer activities
  作者：Vinod Kumar、Kamalneet Kaur、Deepkamal N. Karelia、Vikas Beniwal、Girish Kumar Gupta、Arun K. Sharma、Akhilesh Kumar Gupta

  DOI：10.1016/j.ejmech.2014.05.004

  日期：2014.6

  active agents, regioselective synthesis of a series of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-1-arylethanones 4a–k has been achieved under facile, extremely mild and greener reaction conditions with excellent yields. Moreover, one pot multicomponent reaction has also been reinvestigated under previously reported solvent conditions to prepare 4a–b and found that the reaction generates significant amount of

  在继续努力寻找新的生物活性剂的过程中，在极简单的条件下，已经实现了区域选择性合成一系列2-（3,5-二甲基-1H-吡唑-1-基）-1-芳酮4a – k。温和绿色的反应条件，收率优异。此外，还已经在先前报道的溶剂条件下对一种多釜反应进行了重新研究，以制备4a - b，发现该反应会产生大量副产物。4a - k的化学结构是根据IR，NMR（1 H，13C）光谱，质谱和元素分析。对所有化合物的抗菌，DNA光裂解和抗癌活性进行了评估。其中，2-（3,5-二甲基-1 H-吡唑-1-基）-1-（萘-2-基）乙酮4j对大肠杆菌和金黄色葡萄球菌的抑制作用良好，分别约为50％和25分别为氨苄西林（标准药物）的百分比。化合物4a和4f对铜绿假单胞菌和大肠杆菌显示出相对中等的抑制作用。在DNA光裂解研究中，化合物4c和4d被发现具有很高的活性，并且可以完全降解两种形式的DNA（SC和OC），即使在紫外线照射下的1
• An Efficient Synthesis of Pyrazolyl‐1,2,3‐thiadiazoles <i>via</i> Hurd–Mori Reaction
  作者：Satish Gudala、Srinivasa Rao Ambati、Jeevan Lal Patel、Rajeswar Rao Vedula、Santhosh Penta

  DOI：10.1002/jhet.3609

  日期：2019.8

  An efficient synthetic strategy has been developed for the synthesis of pyrazolyl‐1,2,3‐thiadiazoles via Hurd–Mori cyclization reaction. The reaction of various pyrazolyl‐phenylethanones with semicarbazide hydrochloride in the presence of sodium acetate/methanol gave the corresponding semicarbazones (3a–i). These semicarbazones were further reacted with thionyl chloride via the Hurd–Mori cyclization

  已经开发了一种有效的合成策略，用于通过Hurd-Mori环化反应合成吡唑基1,2,3-噻二唑。在乙酸钠/甲醇存在下，各种吡唑基-苯乙酮与氨基脲盐酸盐的反应得到相应的氨基脲（3a – i）。通过Hurd-Mori环化条件，将这些半咔唑酮与亚硫酰氯进一步反应，以完成标题产物（4a – i）。本方案有利于通过以各种底物以优异的产率形成C-S，NS和C═N键来形成吡唑基半脲酮衍生物和吡唑基1,2,3-噻二唑衍生物。通过分析和光谱研究对最终化合物进行表征。
• Kaur, Kamalneet; Kumar, Vikas; Kumar, Vinod, Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 1, p. 153 - 162
  作者：Kaur, Kamalneet、Kumar, Vikas、Kumar, Vinod

  DOI：——

  日期：——
• Novel inhibitors of nitric oxide synthase with antioxidant properties
  作者：Loredana Salerno、Maria N. Modica、Giuseppe Romeo、Valeria Pittalà、Maria A. Siracusa、Maria E. Amato、Rosaria Acquaviva、Claudia Di Giacomo、Valeria Sorrenti

  DOI：10.1016/j.ejmech.2012.01.002

  日期：2012.3

  We previously described a series of imidazole-based inhibitors substituted at N-1 with an arylethanone chain as interesting inhibitors of neuronal nitric oxide synthase (nNOS), endowed with good selectivity vs endothelial nitric oxide synthase (eNOS). As a follow up of these studies, several analogs characterized by the presence of substituted imidazoles or other mono or bicyclic nitrogen-containing heterocycles instead of simple imidazole were synthesized, and their biological evaluation as in vitro inhibitors of both nNOS and eNOS is described herein. Most of these compounds showed improved nNOS and eNOS inhibitory activity with respect to reference inhibitors. Selected compounds were also tested to analyze their antioxidant properties. Some of them displayed good capacity to scavenge free radicals and ability to reduce lipid peroxidation. (C) 2012 Elsevier Masson SAS. All rights reserved.