(5-(2-hydroxy-3-methylphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)(phenyl)methanone | 1310098-54-4

• 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: (5-(2-hydroxy-3-methylphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)(phenyl)methanone
• 英文别名: [3-(2-Hydroxy-3-methylphenyl)-5-methyl-3,4-dihydropyrazol-2-yl]-phenylmethanone
• CAS: 1310098-54-4
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: GXBNYSSRGIAGID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-4-(2-Hydroxy-3-methyl-phenyl)-but-3-en-2-one 在 4-二甲氨基吡啶 、 一水合肼 、 对甲苯磺酰氯 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 5.0h， 生成 (5-(2-hydroxy-3-methylphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)(phenyl)methanone
  参考文献：
  名称：

  Design and synthesis of N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential antitumor agents

  摘要：

  A series of novel N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential telomerase inhibitors were synthesized. The bioassay tests show that compound 4a exhibited high activity against human gastric cancer cell SGC-7901, liver cancer Hep-G2 and human prostate PC-3 cell lines with IC50 values of 21.23 +/- 0.99, 29.43 +/- 0.32 and 30.89 +/- 1.07 mu M, respectively. All title compounds were assayed for telomerase inhibition by a modified TRAP assay, the results show that compound 4a can inhibit telomerase with IC50 value of 4.0 +/- 0.32 mu M. Docking simulation was performed to position compound 4a into the telomerase (3DU6) active site to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.066

文献信息

• [EN] HETEROCYCLIC AMIDES AS KINASE INHIBITORS<br/>[FR] AMIDES HÉTÉROCYCLIQUES UTILISÉS EN TANT QU'INHIBITEURS DE KINASE
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2016185423A1

  公开（公告）日：2016-11-24

  Disclosed are compounds having the formula: (I) wherein R1, R2, and R3 are as defined herein, and methods of making and using the same.

  揭示的是具有以下式的化合物：(I) 其中R1、R2和R3如本文所定义，并且制备和使用这些化合物的方法。
• Heterocyclic amides as kinase inhibitors
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：US10590085B2

  公开（公告）日：2020-03-17

  Disclosed are compounds having the formula (I): wherein R1, R2, and R3 are as defined herein, and methods of making and using the same.

  公开了具有式 (I) 的化合物： 其中 R1、R2 和 R3 如本文所定义，以及制造和使用它们的方法。
• HETEROCYCLIC AMIDES AS KINASE INHIBITORS
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：EP3298002A1

  公开（公告）日：2018-03-28
• Heterocyclic Amides as Kinase Inhibitors
  申请人：GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED

  公开号：US20210253532A1

  公开（公告）日：2021-08-19

  Disclosed are compounds having the formula: wherein R 1 , R 2 , and R 3 are as defined herein, and methods of making and using the same.
• Design and synthesis of N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential antitumor agents
  作者：Xin-Hua Liu、Ban-Feng Ruan、Jing-Xin Liu、Bao-An Song、Ling-Hong Jing、Jun Li、Yang Yang、Hai-Liang Zhu、Xing-Bao Qi

  DOI：10.1016/j.bmcl.2011.03.066

  日期：2011.5

  A series of novel N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential telomerase inhibitors were synthesized. The bioassay tests show that compound 4a exhibited high activity against human gastric cancer cell SGC-7901, liver cancer Hep-G2 and human prostate PC-3 cell lines with IC50 values of 21.23 +/- 0.99, 29.43 +/- 0.32 and 30.89 +/- 1.07 mu M, respectively. All title compounds were assayed for telomerase inhibition by a modified TRAP assay, the results show that compound 4a can inhibit telomerase with IC50 value of 4.0 +/- 0.32 mu M. Docking simulation was performed to position compound 4a into the telomerase (3DU6) active site to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.