2,3-diphenyl-4,5,6,7-tetrahydro-2H-indazole | 58413-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,3-diphenyl-4,5,6,7-tetrahydro-2H-indazole
• 英文别名: 2H-Indazole, 4,5,6,7-tetrahydro-2,3-diphenyl-；2,3-diphenyl-4,5,6,7-tetrahydroindazole
• CAS: 58413-22-2
• 化学式: C₁₉H₁₈N₂
• 分子量: 274.365
• InChiKey: OSWRAMZIDOQZSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-diphenyl-4,5,6,7-tetrahydro-2H-indazole 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 24.0h， 以69%的产率得到2,3-diphenyl-2H-indazole
  参考文献：
  名称：

  Facile synthesis of 2H-indazole derivatives starting from the Baylis–Hillman adducts of 2-cyclohexen-1-one

  摘要：

  Facile synthetic method of 2H-indazole derivatives was developed involving DDQ oxidation of pyrazoles, which were prepared starting from the Baylis-Hillman adducts of 2-cyclohexen-1-one. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.149
• 作为产物：
  描述：

  4,5,6,7-tetrahydro-2,3-diphenyl-2H-indazole 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 以0.22 g的产率得到2,3-diphenyl-4,5,6,7-tetrahydro-2H-indazole
  参考文献：
  名称：

  Synthesis of hydrogenated indazole derivatives starting with α,β-unsaturated ketones and hydrazine derivatives

  摘要：

  The reaction of hydrazine derivatives with alpha,beta-unsaturated ketones, such as cyclohexenyl(phenyl) methanone and (E)-2-benzylidenecyclohexanone, were investigated.The reaction between methylhydrazine and e.g., cyclohexenyl(phenyl)methanone was particularly interesting as 3a,4,5,6,7,7a-hexahydro-1-methyl-3-phenyl-1H-indazole was obtained as the major product together with 4,5,6,7-tetrahydro-2-methyl-3-phenyl-2H-indazole as a minor product. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.041

文献信息

• 1,3-Diarylcycloalkanopyrazoles and diphenyl hydrazides as selective inhibitors of cyclooxygenase-2
  作者：Zhihua Sui、Jihua Guan、Michael P. Ferro、Kathy McCoy、Michael P. Wachter、William V. Murray、Monica Singer、Michele Steber、Dave M. Ritchie、Dennis C. Argentieri

  DOI：10.1016/s0960-894x(00)00041-x

  日期：2000.3

  cyclooxygenase-2. The 1,3-diaryl substitution pattern of the pyrazole ring in 1 differentiates these compounds from most of the known selective COX-2 inhibitors that contain two aryl rings at the adjacent positions on a heterocyclic or a phenyl ring. Similarly, the two phenyl rings in 2 are also separated by three atoms. SAR of both phenyl rings in 1 and 2, and the aliphatic ring in 1 will be discussed.

  新型1，3-二芳基环烷吡唑1和二苯酰肼2被鉴定为环氧合酶2的选择性抑制剂。吡唑环中1的1,3-二芳基取代模式将这些化合物与大多数已知的选择性COX-2抑制剂区分开，这些抑制剂在杂环或苯环的相邻位置包含两个芳基环。类似地，2中的两个苯环也被三个原子隔开。将讨论1和2中两个苯环和1中脂族环的SAR。
• Microwave-assisted synthesis, biological assessment, and molecular modeling of aza-heterocycles: Potential inhibitory capacity of cholinergic enzymes to Alzheimer's disease
  作者：Efraín Polo、Luis Prent-Peñaloza、Yeray A. Rodríguez Núñez、Lady Valdés-Salas、Jorge Trilleras、Juan Ramos、José A. Henao、Antonio Galdámez、Alejandro Morales-Bayuelo、Margarita Gutiérrez

  DOI：10.1016/j.molstruc.2020.129307

  日期：2021.1

  Abstract A highly regioselective solvent-free microwave-assisted synthesis of pyrazoles and tetrahydroindazoles based on the condensation of 1,3-diketones with arylhydrazines is described. Compounds were evaluated as cholinesterase inhibitors in order to identify an alternative treatment for Alzheimer's disease. All compounds displayed moderated acetylcholinesterase inhibitory activity and most of

  摘要 描述了基于 1,3-二酮与芳基肼缩合的高区域选择性无溶剂微波辅助合成吡唑和四氢吲唑。化合物被评估为胆碱酯酶抑制剂，以确定阿尔茨海默病的替代治疗方法。所有化合物均表现出适度的乙酰胆碱酯酶抑制活性，大多数化合物表现出显着的丁酰胆碱酯酶抑制活性和选择性。化合物 3y 和 3i 的 IC50 分别为 1.65 和 3.59 µM，是作为丁酰胆碱酯酶抑制剂最具活性和选择性的化合物。同样，这些化合物作为抗氧化剂进行了测试，结果表明它们具有捕获自由基的能力。分子对接研究表明，大多数化合物与丁酰胆碱酯酶活性位点内的残基 Trp82 之间存在关键的 π-π 堆积相互作用。在密度泛函理论框架中计算了分子量子相似性场、全局和局部反应性描述符以及福井函数，以分析反应性模式以及分子集。
• Palladium-Catalyzed Coupling of Pyrazole Triflates with Arylboronic Acids
  作者：Curt A. Dvorak、Dale A. Rudolph、Sandy Ma、Nicholas I. Carruthers

  DOI：10.1021/jo0477897

  日期：2005.5.1

  A general protocol for the palladium-mediated Suzuki coupling reaction of pyrazole triflates and aryl boronic acids has been developed. The use of additional dppf ligand was determined to increase product yields allowing for the use of a broad range of reaction substrates.
• Bauer, Annales de Chimie (Cachan, France), 1914, vol. <9> 1, p. 408
  作者：Bauer

  DOI：——

  日期：——
• Synthesis, docking studies and anti-inflammatory activity of 4,5,6,7-tetrahydro-2H-indazole derivatives
  作者：Ornelio Rosati、Massimo Curini、Maria Carla Marcotullio、Antonio Macchiarulo、Marina Perfumi、Laura Mattioli、Francesco Rismondo、Giancarlo Cravotto

  DOI：10.1016/j.bmc.2007.03.006

  日期：2007.5

  A regioselective synthesis of 2,3-disubstituted tetrahydro-2H-indazols, mediated by alpha-zirconium sulfopherylphosphonate-methanephosphonate, was reported. Docking studies into the catalytic site of COX-2 were used to identify potential antiinflammatory lead compounds. Two lead derivatives were chosen endowed with good binding energies and good ADME profiling. The biological in vivo evaluation of these compounds in two different experimental models (Freund's adjuvant-induced arthritis and carrageenan-induced oedema) proved the presence of anti-inflammatory activity. Noteworthy, both compounds evidenced the lack of any gastric injury even at high doses in gastric ulcerogenic assays. (c) 2007 Elsevier Ltd. All rights reserved.