3,5-diphenyl-4-phenylmethyl-1H-pyrazole | 955955-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-diphenyl-4-phenylmethyl-1H-pyrazole
• 英文别名: 4-benzyl-3,5-diphenyl-1H-pyrazole；4-Benzyl-3,5-diphenyl-1H-pyrazole
• CAS: 955955-05-2
• 化学式: C₂₂H₁₈N₂
• 分子量: 310.398
• InChiKey: KDONMHUFKXSVDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-diphenyl-4-phenylmethyl-1H-pyrazole 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 9-(4-Benzyl-3,5-diphenyl-pyrazol-1-yl)-nonanoic acid
  参考文献：
  名称：

  Structure-activity relationships associated with 3,4,5-triphenyl-1H-pyrazole-1-nonanoic acid, a nonprostanoid prostacyclin mimetic

  摘要：

  A series of phenylated pyrazoloalkanoic acid derivatives were synthesized and evaluated as inhibitors of ADP-induced human platelet aggregation. 3,4,5-Triphenyl-1H-pyrazole-1-nonanoic acid (8d), with an 1C50 of 0.4-mu-M, was the most potent inhibitor identified in this study. Biochemical studies determined that 8d increased intraplatelet cAMP accumulation and stimulated platelet membrane-bound adenylate cyclase in a concentration-dependent fashion. Displacement of [H-3]iloprost by 8d from platelet membranes indicated that the platelet prostacyclin (PGI2) receptor is the locus of biological action. Structure-activity studies demonstrated that the minimum structural requirements for binding to the platelet PGI2 receptor and inhibition of ADP-induced platelet aggregation within this series are a vicinally diphenylated pyrazole substituted with an omega-alkanoic acid side chain eight or nine atoms long. Potency depended upon both side-chain length and its topological relationship with the two phenyl rings.

  DOI：

  10.1021/jm00080a028
• 作为产物：
  描述：

  2-苄基-1,3-二苯基丙烷-1,3-二酮 在 肼 作用下， 以 乙醇 为溶剂， 生成 3,5-diphenyl-4-phenylmethyl-1H-pyrazole
  参考文献：
  名称：

  Structure-activity relationships associated with 3,4,5-triphenyl-1H-pyrazole-1-nonanoic acid, a nonprostanoid prostacyclin mimetic

  摘要：

  A series of phenylated pyrazoloalkanoic acid derivatives were synthesized and evaluated as inhibitors of ADP-induced human platelet aggregation. 3,4,5-Triphenyl-1H-pyrazole-1-nonanoic acid (8d), with an 1C50 of 0.4-mu-M, was the most potent inhibitor identified in this study. Biochemical studies determined that 8d increased intraplatelet cAMP accumulation and stimulated platelet membrane-bound adenylate cyclase in a concentration-dependent fashion. Displacement of [H-3]iloprost by 8d from platelet membranes indicated that the platelet prostacyclin (PGI2) receptor is the locus of biological action. Structure-activity studies demonstrated that the minimum structural requirements for binding to the platelet PGI2 receptor and inhibition of ADP-induced platelet aggregation within this series are a vicinally diphenylated pyrazole substituted with an omega-alkanoic acid side chain eight or nine atoms long. Potency depended upon both side-chain length and its topological relationship with the two phenyl rings.

  DOI：

  10.1021/jm00080a028

文献信息

• Regioselective One-Step Synthesis of Pyrazoles from Alkynes and N-Tosylhydrazones: [3+2] Dipolar Cycloaddition/[1,5] Sigmatropic Rearrangement Cascade
  作者：M. Carmen Pérez-Aguilar、Carlos Valdés

  DOI：10.1002/anie.201301284

  日期：2013.7.8

  Rearrangement under control: A wide variety of 3,4,5‐ and 1,3,5‐trisubstituted pyrazoles can be prepared from tosylhydrazones of ketones and terminal alkynes through the title reaction sequence (see scheme; Ts=4‐toluenesulfonyl). The rearrangement, and therefore, the regioselectivity of the reaction is controlled by the nature of the substituents of the tosylhydrazone.

  在控制下进行重排：可以通过标题反应顺序（参见方案； Ts = 4-甲苯磺酰基），从酮和末端炔烃的甲苯磺酰prepared制备各种各样的3,4,5-和1,3,5-三取代的吡唑。反应的重排以及因此的区域选择性由甲苯磺酰hydr的取代基的性质控制。
• The reaction of acetylenes with aldazines in the NaOBut/DMSO system: a contribution to the pyrazole chemistry
  作者：Ivan A. Bidusenko、Elena Yu. Schmidt、Nadezhda I. Protsuk、Igor A. Ushakov、Boris A. Trofimov

  DOI：10.1016/j.mencom.2024.01.033

  日期：2024.1

  [Display omitted]

  [显示省略]