3,5-diphenyl-4-ethyl-1H-pyrazole | 62625-79-0

• 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-ethyl-1H-pyrazole
• 英文别名: 4-ethyl-3,5-diphenyl-1H-pyrazole；4-ethyl-3,5-diphenyl-1H-pyrazole；4-Aethyl-3,5-diphenyl-1H-pyrazol
• CAS: 62625-79-0
• 化学式: C₁₇H₁₆N₂
• 分子量: 248.327
• InChiKey: BVRQBYJQQOIEFG-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 沸点：
  470.9±34.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-ethyl-1H-pyrazole 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 9-(4-Ethyl-3,5-diphenylpyrazol-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：

  phenylmagnesium bromide 在 一水合肼 、 甲苯 作用下， 生成 3,5-diphenyl-4-ethyl-1H-pyrazole
  参考文献：
  名称：

  Mavrodin, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1929, vol. 188, p. 1505

  摘要：

  DOI：

文献信息

• NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS
  申请人：ATOBE Masakazu

  公开号：US20100029690A1

  公开（公告）日：2010-02-04

  Nitrogen-containing heterocyclic compounds represented by the following Formula (1) are provided. The compounds or salts thereof have a strong EP1 antagonistic activity when they are administered to a human or an animal, and they are useful as an effective component of a pharmaceutical agent for prophylaxis and/or treatment of an overactive bladder, for example. Furthermore, they are useful as an effective component of a pharmaceutical agent for the prophylaxis and/or treatment of symptoms including frequent urination, urinary urgency and urinary incontinence.

  提供以下式（1）所代表的含氮杂环化合物。当这些化合物或其盐被给予人类或动物时，它们具有强烈的EP1拮抗活性，并且它们作为预防或治疗过度活动膀胱的药物的有效成分是有用的，例如。此外，它们作为预防或治疗包括频繁排尿、尿急和尿失禁等症状的药物的有效成分是有用的。
• 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。
• NITROGENATED HETEROCYCLIC COMPOUND
  申请人：Asahi Kasei Pharma Corporation

  公开号：EP2314587A1

  公开（公告）日：2011-04-27

  Nitrogen-containing heterocyclic compounds represented by the following Formula (1) are provided. The compounds or salts thereof have a strong EP1 antagonistic activity when they are administered to a human or an animal, and they are useful as an effective component of a pharmaceutical agent for prophylaxis and/or treatment of an overactive bladder, for example. Furthermore, they are useful as an effective component of a pharmaceutical agent for the prophylaxis and/or treatment of symptoms including frequent urination, urinary urgency and urinary incontinence.

  本发明提供了由下式（1）代表的含氮杂环化合物。这些化合物或其盐类在给人或动物用药时具有很强的 EP1 拮抗活性，可作为预防和/或治疗膀胱过度活动症等药物的有效成分。此外，它们还是预防和/或治疗尿频、尿急和尿失禁等症状的药剂的有效成分。
• SAR-based optimization of 2-(1H-pyrazol-1-yl)-thiazole derivatives as highly potent EP1 receptor antagonists
  作者：Masakazu Atobe、Kenji Naganuma、Masashi Kawanishi、Akifumi Morimoto、Ken-ichi Kasahara、Shigeki Ohashi、Hiroko Suzuki、Takahiko Hayashi、Shiro Miyoshi

  DOI：10.1016/j.bmcl.2013.10.065

  日期：2013.12

  We describe a medicinal chemistry approach for generating a series of 2-(1H-pyrazol-1-yl)thiazoles as EP1 receptor antagonists. To improve the physicochemical properties of compound 1, we investigated its structure-activity relationships (SAR). Optimization of this lead compound provided small compound 25 which exhibited the best EP1 receptor antagonist activity and a good SAR profile. (C) 2013 Elsevier Ltd. All rights reserved.
• v. Auwers; Bergmann, Justus Liebigs Annalen der Chemie, 1929, vol. 472, p. 310
  作者：v. Auwers、Bergmann

  DOI：——

  日期：——