1-(4-methoxyphenyl)-1,5,6,7-tetrahydro-4H-indazol-4-one | 945363-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-methoxyphenyl)-1,5,6,7-tetrahydro-4H-indazol-4-one
• 英文别名: 1-(4-methoxyphenyl)-6,7-dihydro-5H-indazol-4-one；1-(4-methoxylphenyl)-1,5,6,7-tetrahydroindazol-4-one；1-(4-Methoxyphenyl)-6,7-dihydro-1H-indazol-4(5H)-one
• CAS: 945363-51-9
• 化学式: C₁₄H₁₄N₂O₂
• mdl: MFCD09462320
• 分子量: 242.277
• InChiKey: LOYJCZAMYSLPAW-UHFFFAOYSA-N

物化性质

• 熔点：
  142-144 °C
• 沸点：
  411.9±33.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-1,5,6,7-tetrahydro-4H-indazol-4-one 在 盐酸羟胺 、 sodium acetate 、 sodium iodide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 水 、 异丙醇 为溶剂， 反应 4.5h， 生成 N-[1-(4-methoxyphenyl)indazol-4-yl]acetamide
  参考文献：
  名称：

  A novel synthetic approach to 4-acetamido-1-arylindazoles via Semmler–Wolff rearrangement of 1-aryl-6,7-dihydro-5H-indazol-4-one oxime

  摘要：

  A simple and efficient procedure for the syntheses of 4-acetamido-1-arylindazoles from corresponding 1-aryl-6,7-dihydro-5H-indazol-4-one oximes by Semmler-Wolff aromatization using acetic anhydride and sodium iodide is reported. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.058
• 作为产物：
  描述：

  1,3-环己二酮 在 盐酸 作用下， 以 水 、 异丙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 1-(4-methoxyphenyl)-1,5,6,7-tetrahydro-4H-indazol-4-one
  参考文献：
  名称：

  A novel synthetic approach to 4-acetamido-1-arylindazoles via Semmler–Wolff rearrangement of 1-aryl-6,7-dihydro-5H-indazol-4-one oxime

  摘要：

  A simple and efficient procedure for the syntheses of 4-acetamido-1-arylindazoles from corresponding 1-aryl-6,7-dihydro-5H-indazol-4-one oximes by Semmler-Wolff aromatization using acetic anhydride and sodium iodide is reported. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.058

文献信息

• Catalyst-free one-pot synthesis of 1,4,5-trisubstituted pyrazoles in 2,2,2-trifluoroethanol
  作者：Heshmatollah Alinezhad、Mahmood Tajbakhsh、Mahboobeh Zare

  DOI：10.1016/j.jfluchem.2011.07.014

  日期：2011.11

  A simple, efficient and three component one-pot synthesis of 1,4,5-trisubstituted pyrazoles by condensation of β-dicarbonyls, N,N-dimethylformamide dimethyl acetal (DMFDMA) and hydrazine derivatives in 2,2,2-trifluoroethanol without using any catalyst and activation, is described.

  通过在不使用2,2,2-三氟乙醇的条件下将β-二羰基，N，N-二甲基甲酰胺二甲基乙缩醛（DMFDMA）和肼衍生物缩合的简单，有效的三组分一锅法合成1,4,5-三取代的吡唑描述了任何催化剂和活化。
• Identification, Synthesis, and Pharmacological Evaluation of Tetrahydroindazole Based Ligands as Novel Antituberculosis Agents
  作者：Songpo Guo、Yang Song、Qingqing Huang、Hai Yuan、Baojie Wan、Yuehong Wang、Rong He、Maria G. Beconi、Scott G. Franzblau、Alan P. Kozikowski

  DOI：10.1021/jm901235p

  日期：2010.1.28

  The resurgence Of tuberculosis (TB), the incidence of drug-resistant strains of Mycobacterium tuberculosis (MTB), and the coinfection between TB and HIV have led to serious infections, high mortality, and it global health threat, resulting in the urgent search for new classes of antimycobacterial agents. Herein, we report the identification of a novel class of tetrahydroindazole based compounds as potent and unique inhibitors of MTB. Compounds 6a, 6m, and 6q exhibited activity in the low micromolar range against replicating Mycobacterium tuberculosis (R-TB) phenotype, with minimum inhibitory concentrations (MICs) of 1.7, 1.9, and 1.9 mu M, respectively, while showing no toxicity to Vero Ccells, Moreover, studies aimed to assess the in vitro metabolic stability of 6a and 6m in mouse liver microsomes and in vivo pharmacokinetic profiles in plasma levels gave satisfactory results. This research suggests that tetrahydroindazole based anti-TB compounds can serve its a promising lead scaffold in developing new drugs to combat tuberculosis infections.
• Pyrazolo[3,4-h]quinolines promising photosensitizing agents in the treatment of cancer
  作者：Virginia Spanò、Barbara Parrino、Anna Carbone、Alessandra Montalbano、Alessia Salvador、Paola Brun、Daniela Vedaldi、Patrizia Diana、Girolamo Cirrincione、Paola Barraja

  DOI：10.1016/j.ejmech.2015.08.003

  日期：2015.9

  A new series of pyrazolo[3,4-h]quinolines, heteroanalogues of angelicin was conveniently prepared with a broad substitution pattern. A large number of derivatives was obtained and the cellular photocytotoxicity was evaluated in vitro against 5 different human tumor cell lines with GI(50) values reaching the nanomolar level (14.52-0.04 mu M). Selected compounds were able to photoinduce a massive cell death with the involvement of mitochondria. Their photodamage cellular targets were proteins and lipids and they did not cause any kind of DNA photodamage. This latter event is of considerable importance in the modulation of long term side effects, generally associated with the use of classical furocoumarins. (C) 2015 Elsevier Masson SAS. All rights reserved.