3-(2-nitrophenyl)-4,5-dihydro-1H-pyrazole | 361443-02-9

• 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: 3-(2-nitrophenyl)-4,5-dihydro-1H-pyrazole
• CAS: 361443-02-9
• 化学式: C₉H₉N₃O₂
• 分子量: 191.189
• InChiKey: ROLZHFDXTPZNIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-nitrophenyl)-4,5-dihydro-1H-pyrazole 在 三乙胺 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-(2-aminophenyl)-1-phenylpropanoyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group

  摘要：

  In a preliminary article, we reported a series of 4,5-dihydro-1H-pyrazole derivatives as neuronal nitric oxide synthase (nNOS) inhibitors. Here we present the data about the inhibition of inducible nitric oxide synthase (iNOS) of these compounds. In general, we can confirm that these pyrazoles are nNOS selective inhibitors. In addition, taking these compounds as a reference, we have designed and synthesized a series of new derivatives by modification of the heterocycle in 1-position, and by introduction of electrondonating or electron-withdrawing substituents in the aromatic ring. These derivatives have been evaluated as nNOS and iNOS inhibitors in order to identify new compounds with improved activity and selectivity. Compound 3r, with three methoxy electron-donating groups in the phenyl moiety, is the most potent nNOS inhibitor, showing good selectivity nNOS/iNOS. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.016
• 作为产物：
  描述：

  1-(2-硝基苯基)-2-丙烯-1-醇 在 Jones reagent 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 3.0h， 生成 3-(2-nitrophenyl)-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group

  摘要：

  In a preliminary article, we reported a series of 4,5-dihydro-1H-pyrazole derivatives as neuronal nitric oxide synthase (nNOS) inhibitors. Here we present the data about the inhibition of inducible nitric oxide synthase (iNOS) of these compounds. In general, we can confirm that these pyrazoles are nNOS selective inhibitors. In addition, taking these compounds as a reference, we have designed and synthesized a series of new derivatives by modification of the heterocycle in 1-position, and by introduction of electrondonating or electron-withdrawing substituents in the aromatic ring. These derivatives have been evaluated as nNOS and iNOS inhibitors in order to identify new compounds with improved activity and selectivity. Compound 3r, with three methoxy electron-donating groups in the phenyl moiety, is the most potent nNOS inhibitor, showing good selectivity nNOS/iNOS. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.016

文献信息

• Pyrazoline derivative or tetrahydropyridazine derivative and medicinal use thereof
  申请人：——

  公开号：US20030149046A1

  公开（公告）日：2003-08-07

  Using a compound selected from compounds represented by the following formula (1) 1 (which include 3-phenyl-2-pyrazoline derivatives and 3-phenyl-tetrahydropyridazine derivatives) and pharmacologically acceptable salts thereof, an agent is provided which can activate glutamic acid transporter and which is useful for prevention and/treatment of cerebral ischemia (cerebral infarct and brain edema), amyotrophic lateral sclerosis (ALS), etc., all caused by glutamic acid toxicity.

  使用以下公式（1）代表的化合物中选择的一种化合物（其中包括3-苯基-2-吡唑啉衍生物和3-苯基-四氢吡啶衍生物）及其药理学上可接受的盐，提供了一种可以激活谷氨酸转运蛋白并对由谷氨酸毒性引起的脑缺血（脑梗死和脑水肿）、肌萎缩侧索硬化症（ALS）等疾病进行预防和/或治疗的药剂。
• PYRAZOLINE DERIVATIVES OR TETRAHYDROPYRIDAZINE DERIVATIVES AND MEDICINAL USE THEREOF
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1270567A1

  公开（公告）日：2003-01-02

  Using a compound selected from compounds represented by the following formula (1) (which include 3-phenyl-2-pyrazoline derivatives and 3-phenyl-tetrahydropyridazine derivatives) and pharmacologically acceptable salts thereof, an agent is provided which can activate glutamic acid transporter and which is useful for prevention and/treatment of cerebral ischemia (cerebral infarct and brain edema), amyotrophic lateral sclerosis (ALS), etc., all caused by glutamic acid toxicity.

  使用选自下式 (1) 所代表的化合物（包括 3-苯基-2-吡唑啉衍生物和 3-苯基-四氢哒嗪衍生物）及其药理学可接受盐的化合物 (其中包括 3-苯基-2-吡唑啉衍生物和 3-苯基-四氢哒嗪衍生物）及其药理上可接受的盐，提供了一种可激活谷氨酸转运体的制剂，该制剂可用于预防和/或治疗谷氨酸毒性引起的脑缺血（脑梗塞和脑水肿）、肌萎缩性脊髓侧索硬化症（ALS）等。
• US6831083B2
  申请人：——

  公开号：US6831083B2

  公开（公告）日：2004-12-14
• Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group
  作者：M. Dora Carrión、Mariem Chayah、Antonio Entrena、Ana López、Miguel A. Gallo、Darío Acuña-Castroviejo、M. Encarnación Camacho

  DOI：10.1016/j.bmc.2013.05.016

  日期：2013.7

  In a preliminary article, we reported a series of 4,5-dihydro-1H-pyrazole derivatives as neuronal nitric oxide synthase (nNOS) inhibitors. Here we present the data about the inhibition of inducible nitric oxide synthase (iNOS) of these compounds. In general, we can confirm that these pyrazoles are nNOS selective inhibitors. In addition, taking these compounds as a reference, we have designed and synthesized a series of new derivatives by modification of the heterocycle in 1-position, and by introduction of electrondonating or electron-withdrawing substituents in the aromatic ring. These derivatives have been evaluated as nNOS and iNOS inhibitors in order to identify new compounds with improved activity and selectivity. Compound 3r, with three methoxy electron-donating groups in the phenyl moiety, is the most potent nNOS inhibitor, showing good selectivity nNOS/iNOS. (C) 2013 Elsevier Ltd. All rights reserved.