2-(3,4-dimethylphenyl)-5-phenyl-2,4-dihydropyrazol-3-one | 374924-87-5

• 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: 2-(3,4-dimethylphenyl)-5-phenyl-2,4-dihydropyrazol-3-one
• 英文别名: 1-(3,4-Dimethylphenyl)-3-phenyl-3-pyrazolin-5-one；2-(3,4-dimethylphenyl)-5-phenyl-2,4-dihydropyrazole-3-one；2-(3,4-dimethylphenyl)-5-phenyl-4H-pyrazol-3-one
• CAS: 374924-87-5
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: JSCLBWOECQERRY-UHFFFAOYSA-N

物化性质

• 沸点：
  422.1±55.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethylphenyl)-5-phenyl-2,4-dihydropyrazol-3-one 在 硫酰氟 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到1-(3,4-dimethylphenyl)-3-phenyl-1H-pyrazol-5-yl sulfurofluoridate
  参考文献：
  名称：

  SO 2 F 2介导的吡唑啉酮向吡唑基氟代硫酸盐的转化

  摘要：

  通过吡唑啉酮与SO 2 F 2的反应，以良好至极好的收率，可以实现一类同时具有吡唑和氟硫酸盐官能团的新型N-杂环分子的构建。在Suzuki偶联反应和SuFEx click化学中，氟代硫酸盐部分被用作通用的结构单元。

  DOI：

  10.1039/c9ob00903e
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 、 3,4-二甲基苯肼 在 溶剂黄146 作用下， 反应 24.0h， 以55%的产率得到2-(3,4-dimethylphenyl)-5-phenyl-2,4-dihydropyrazol-3-one
  参考文献：
  名称：

  Hydrazinonaphthalene and Azonaphthalene Thrombopoietin Mimics Are Nonpeptidyl Promoters of Megakaryocytopoiesis

  摘要：

  High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC50 values in the region of 1-20 nM.

  DOI：

  10.1021/jm010283l

文献信息

• Thrombopoietin mimetics
  申请人：——

  公开号：US20040019190A1

  公开（公告）日：2004-01-29

  Invented are non-peptide TPO mimetics. Also invented are novel processes and intermediates used in the preparation of the presently invented compounds. Also invented is a method of treating thrombocytopenia, in a mammal, including a human, in need thereof which comprises administering to such mammal an effective amount of a selected hydroxy- 1 -azobenzene derivative.

  发明了非肽类TPO类似物。还发明了用于制备目前发明的化合物的新工艺和中间体。还发明了一种治疗血小板减少症的方法，包括给予需要的哺乳动物，包括人类，有效量的选择性羟基-1-偶氮苯衍生物。
• THROMBOPOIETIN MIMETICS
  申请人：Duffy Kevin J.

  公开号：US20130078213A1

  公开（公告）日：2013-03-28

  Invented are non-peptide TPO mimetics. Also invented are novel processes and intermediates used in the preparation of the presently invented compounds. Also invented is a method of treating thrombocytopenia, in a mammal, including a human, in need thereof which comprises administering to such mammal an effective amount of a selected hydroxy-1-azobenzene derivative.

  本发明涉及非肽类TPO类似物的发明。本发明还涉及用于制备目前发明的化合物的新型过程和中间体。本发明还涉及一种治疗血小板减少症的方法，包括在需要的哺乳动物（包括人类）中给予所选的羟基-1-偶氮苯衍生物的有效量。
• Fluorosulfate-containing pyrazole heterocycles as selective BuChE inhibitors: structure-activity relationship and biological evaluation for the treatment of Alzheimer’s disease
  作者：Huan-Huan Li、Chengyao Wu、Shi-Long Zhang、Jian-Guo Yang、Hua-Li Qin、Wenjian Tang

  DOI：10.1080/14756366.2022.2103553

  日期：2022.12.31

  Abstract Novel scaffolds are expected to treat Alzheimer’s disease, pyrazole-5-fluorosulfates were found as selective BuChE inhibitors. Compounds K1–K26 were assayed for ChE inhibitory activity, amongst them, compound K3 showed potent BuChE and hBuChE inhibition (IC50 = 0.79 μM and 6.59 μM). SAR analysis showed that 1-, 3-, 4-subtituent and 5-fluorosulfate of pyrazole ring affected BuChE inhibitory

  摘要 新型支架有望治疗阿尔茨海默病，发现 pyrazole-5-fluorosulfate 作为选择性 BuChE 抑制剂。对化合物K1-K26的 ChE 抑制活性进行了测定，其中，化合物K3显示出有效的 BuChE 和h BuChE 抑制作用（IC 50 = 0.79 μM 和 6.59 μM）。SAR分析表明吡唑环的1-、3-、4-取代基和5-氟硫酸盐影响BuChE抑制活性。分子对接表明，氟硫酸盐通过π-硫相互作用增加了h BuChE的结合亲和力。化合物K3是一种可逆的、混合的、非竞争性的 BuChE 抑制剂（K i= 0.77 μM）并显示出显着的神经保护作用、安全的毒理学特征和 BBB 渗透。体内行为研究表明，K3治疗改善了 A β 1 - 42诱导的认知障碍，并显着阻止了 A β 1 - 42毒性的影响。因此，选择性 BuChE 抑制剂K3具有作为 AD 治疗剂进一步开发的潜力。
• EP1294378A4
  申请人：——

  公开号：EP1294378A4

  公开（公告）日：2004-01-28
• [EN] THROMBOPOIETIN MIMETICS<br/>[FR] MIMIQUES DE THROMBOPOIETINE
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2001089457A2

  公开（公告）日：2001-11-29

  Invented are non-peptide TPO mimetics. Also invented are novel processes and intermediates used in the preparation of the presently invented compounds. Also invented is a method of treating thrombocytopenia, in a mammal, including a human, in need thereof which comprises administering to such mammal an effective amount of a selected hydroxy-1-azobenzene derivative.