5,7-dimethyl-[3-(4-fluoro-phenylsulfonyl)-pyrazolo[1,5-a]pyrimidin-2-yl]-methyl-amine | 1173163-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 5,7-dimethyl-[3-(4-fluoro-phenylsulfonyl)-pyrazolo[1,5-a]pyrimidin-2-yl]-methyl-amine
• 英文别名: N-{3-[(4-Fluorophenyl)sulfonyl]-5,7-dimethylpyrazolo[1,5-A]pyrimidin-2-YL}-N-methylamine；3-(4-fluorophenyl)sulfonyl-N,5,7-trimethylpyrazolo[1,5-a]pyrimidin-2-amine
• CAS: 1173163-32-0
• 化学式: C₁₅H₁₅FN₄O₂S
• mdl: MFCD32681029
• 分子量: 334.374
• InChiKey: KDUSPNDDQIZEGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(4-fluorophenylsulfonyl)-N(3)-methyl-1H-pyrazole-3,5-diamine 、 乙酰丙酮 在 溶剂黄146 作用下， 生成 5,7-dimethyl-[3-(4-fluoro-phenylsulfonyl)-pyrazolo[1,5-a]pyrimidin-2-yl]-methyl-amine
  参考文献：
  名称：

  Synthesis and SAR of 3-arylsulfonyl-pyrazolo[1,5-a]pyrimidines as potent serotonin 5-HT6 receptor antagonists

  摘要：

  Syntheses of a series of novel 3-sulfonyl-pyrazolo[1,5-a]pyrimidines and their 5-HT6 receptor antagonistic structure-activity relationship are disclosed. The nature and position of substituents, which affect their receptor antagonistic activity, are analyzed. Among all synthesized derivatives, {3-(3-chlorophenylsulfonyl)-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-2-yl}-methyl-amine 33 (K-i = 190 pM), (3-phenylsulfonyl-7-methyl-pyrazolo[1,5-a]pyrimidin-2-yl)-methyl-amine 44 (K-i = 240 pM), (3-phenylsulfonyl-5-metoxymethyl-7-methyl-pyrazolo[1,5-a]pyrimidin-2-yl)-methyl-amine 50 (K-i = 270 pM), and (3-phenylsulfonyl-5-methyl-7-metoxymethyl-pyrazolo[1,5-a]pyrimidin-2-yl)-methyl-amine 52 (K-i = 280 pM) are the most potent antagonists of the 5-HT6 receptors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.055

文献信息

• SUBSTITUTED 2-AMINO-3-SULFONYL-PYRAZOLO[1,5-A] PYRIMIDINES/ANTAGONISTS OF SEROTONIN 5-HT6 RECEPTORS, METHODS FOR THE PRODUCTION AND THE USE THEREOF
  申请人：Alla Chem, LLC.

  公开号：EP2248817B1

  公开（公告）日：2015-01-07
• (EN) SUBSTITUTED 2-AMINO-3-SULFONYL-PYRAZOLO[1,5-A] PYRIMIDINES/ANTAGONISTS OF SEROTONIN 5-HT6 RECEPTORS, METHODS FOR THE PRODUCTION AND THE USE THEREOF
  申请人：IVASHCHENKO Andrey Alexandrovich

  公开号：US20100292245A1

  公开（公告）日：2010-11-18

  The present invention relates to novel substituted 2-amino-3-(arylsulfonyl)pyrazolo[1,5-a]pyrimidines of general formula 1, to serotonin 5-HT 6 receptor antagonists, to novel drug substances and pharmaceutical compositions, to medicaments, methods for preparation thereof, and to methods for prophylaxis and treatment of various CNS diseases, pathogenesis of which is associated with disturbance of monoaminergic signaling pathways, more specifically over- or hypo-activation of serotonin 5-HT 6 receptors. Ar represents optionally substituted aryl or optionally substituted heterocyclyl; R 1 and R 3 independently of each other represent C 1 -C 3 alkyl or aryl; R 2 represents hydrogen or C 1 -C 3 alkyl; R 4 1 , and R 4 2 independently of each other represent hydrogen, optionally substituted C 1 -C 3 alkyl or optionally substituted phenyl, or R 4 1 , and R 4 2 together with nitrogen atom they are attached to form optionally substituted heterocyclyl.
• Substitute 2-amino-3-(Sulfony)pyrazol[1,5-a]pyramidines - serotonin 5-ht6 receptor antagonists, method for us thereof
  申请人：Ivashtchenko Alexander Vasilievich

  公开号：US20130079350A1

  公开（公告）日：2013-03-28

  The present invention relates to novel substituted 2-amino-3-(arylsulfonyl)pyrazolo[1,5-a]pyrimidines of general formula 1, to serotonin 5-HT 6 receptor antagonists, to novel drug substances and pharmaceutical compositions, to medicaments, methods for preparation thereof, and to methods for prophylaxis and treatment of various CNS diseases, pathogenesis of which is associated with disturbance of monoaminergic signaling pathways, more specifically over- or hypo-activation of serotonin 5-HT 6 receptors. In general formula 1 R 1 and R 3 independently of each other represent C 1 -C 3 alkyl or phenyl; R 2 represents hydrogen or C 1 -C 3 alkyl; R 4 1 , R 4 2 independently of each other represent hydrogen, optionally substituted C 1 -C 3 alkyl or optionally substituted phenyl, or R 4 1 and R 4 2 together with the nitrogen atom they are attached to form optionally substituted heterocyclyl; Ar is aryl selected from phenyl, optionally substituted with R i 5 that is one or two optionally identical substituents selected from hydrogen, lower alkyl, trifluoromethyl or halogen; or optionally substituted 5-6-membered heteroaryl, containing as the heteroatom nitrogen or sulfur atom.
• US8309559B2
  申请人：——

  公开号：US8309559B2

  公开（公告）日：2012-11-13
• US8829009B2
  申请人：——

  公开号：US8829009B2

  公开（公告）日：2014-09-09