N,5,7-trimethyl-3-(phenylsulfonyl)pyrazolo[1,5-a]pyrimidin-2-amine | 1173163-30-8

• 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: N,5,7-trimethyl-3-(phenylsulfonyl)pyrazolo[1,5-a]pyrimidin-2-amine
• 英文别名: 3-(benzenesulfonyl)-N,5,7-trimethylpyrazolo[1,5-a]pyrimidin-2-amine
• CAS: 1173163-30-8
• 化学式: C₁₅H₁₆N₄O₂S
• mdl: MFCD20231904
• 分子量: 316.384
• InChiKey: YPVOSIDECMYMTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 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：
  5

反应信息

• 作为产物：
  描述：

  N(3)-methyl-4-(phenylsulfonyl)-1H-pyrazole-3,5-diamine 、 乙酰丙酮 在 溶剂黄146 作用下， 反应 3.0h， 生成 N,5,7-trimethyl-3-(phenylsulfonyl)pyrazolo[1,5-a]pyrimidin-2-amine
  参考文献：
  名称：

  2-Substituted 5,6-dimethyl-3-phenylsulfonyl-pyrazolo[1,5-a]pyrimidines: New series of highly potent and specific serotonin 5-HT6 receptor antagonists

  摘要：

  Syntheses, biological evaluation, and structure activity relationships for a series of novel 2-substituted 3-benzenesulfonyl-5,6-dimethyl-pyrazolo[1,5-a]pyrimidines are disclosed. In spite of a wide, four orders of magnitude, SAR range (K-i varied from 260 pM to 2.96 mu M), no significant correlation of 5-HT6R antagonistic potency was observed with major physiochemical characteristics, such as molecular weight, surface polar area, cLogP, or number of rotatable bonds. Statistically significant trend was only observed for size of substitute group, which was not enough to explain the deep SAR trend. Besides with the substitute group size, another factor that presumably plays a role in defining the compound potencies is a relative position of the heterocycle and sulfophenyl moieties. Among all synthesized derivatives, (3-benzenesulfonyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-2-yl)-methyl-amine 18 is the most potent (K-i = 260 pM) and extremely selective, 5000 to >50,000-fold relative to 55 therapeutic targets, antagonist of the 5-HT6 receptor. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.038

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