8-[4-[4-(4-氯苄基)哌嗪-1-磺酰基)苯基]-1-丙基黄嘌呤 | 1027513-54-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 8-[4-[4-(4-氯苄基)哌嗪-1-磺酰基)苯基]-1-丙基黄嘌呤
• 英文名称: PSB 0788
• 英文别名: 8-[4-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]sulfonylphenyl]-1-propyl-3,7-dihydropurine-2,6-dione；8-(4-(4-(4-chlorobenzyl)piperazine-1-sulfonyl)phenyl)-1-propyl-3,7-dihydropurine-2,6-dione；8-(4-(4-(4-chlorobenzyl)piperazine-1-sulfonyl)phenyl)-1-propylxanthine；PSB-0788；8-(4-{4-[(4-chlorophenyl)methyl]piperazine-1-sulfonyl}phenyl)-1-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• CAS: 1027513-54-7
• 化学式: C₂₅H₂₇ClN₆O₄S
• 分子量: 543.046
• InChiKey: JQZJACVYMPKVDS-UHFFFAOYSA-N

物化性质

• 熔点：
  >292 °C (decomp)
• 密度：
  1.414±0.06 g/cm3(Predicted)
• 溶解度：
  溶于 DMSO > 10 mM

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(4-氯苄基)哌嗪 、 1-propyl-8-[4-[[[p-nitrophenyl]oxy]sulfonyl]phenyl]xanthine 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 以64%的产率得到8-[4-[4-(4-氯苄基)哌嗪-1-磺酰基)苯基]-1-丙基黄嘌呤
  参考文献：
  名称：

  1-Alkyl-8-(piperazine-1-sulfonyl)phenylxanthines: Development and Characterization of Adenosine A_2B Receptor Antagonists and a New Radioligand with Subnanomolar Affinity and Subtype Specificity

  摘要：

  A new series of 1-alkyl-8-(piperazine-1-sulfonyl)phenylxanthines was designed, synthesized, and characterized in radioligand binding and functional assays at A(2B) adenosine receptors. A(2B) antagonists with subnanomolar affinity and high selectivity were discovered. The most potent compounds were 1-ethyl-8-(4-(4-(4-trifluoromethylbenzyl)piperazine-1-sulfonyl)phenyl)xanthine (24, PSB-09120, K-i (human A(2B)) = 0. 157 nM) and 8-(4-(4-(4-chlorobenzyl)piperazine-1-sulfonyl)phenyl)-1-propylxanthine (17, PSB-0788, K-i (human A2(B)) = 0.393 nM). Moreover, 8-(4-(4-(4-chlorophenyl)piperazine-1-sulfonyl)phenyl)-1-propylxanthine (35, PSB-603) was developed as an A(2B)-specific antagonist exhibiting a Ki value of 0.553 nM at the human A2B receptor and virtually no affinity for the human and rat A(1) and A(2A) and the human A(3) receptors up to a concentration of 10 mu M. A tritiated form of the compound was prepared as a new radioligand and characterized in kinetic, saturation, and competition studies. It was shown to be a useful pharmacological tool for the selective labeling of human as well as rodent A(2B) receptors (K-D human A(2B) 0.403 nM, mouse A(2B) 0.351 nM).

  DOI：

  10.1021/jm900413e

文献信息

• Methods and Compositions for Treating Cancer
  申请人：Omeros Corporation

  公开号：US20200345725A1

  公开（公告）日：2020-11-05

  This disclosure is directed to compounds, compositions, and methods for the treatment of various diseases and/or conditions related to G protein-coupled receptor 174 (e.g., cancers).
• [EN] REDUCING DIABETES IN PATIENTS RECEIVING HMG-COA REDUCTASE INHIBITORS (STATINS)<br/>[FR] RÉDUCTION DE DIABÈTE CHEZ DES PATIENTS RECEVANT DES INHIBITEURS DE L'HMG-COA RÉDUCTASE (STATINES)
  申请人：JOLLA INST ALLERGY IMMUNOLOG

  公开号：WO2014153424A1

  公开（公告）日：2014-09-25

  The invention provides compositions, methods and uses for reducing insulin resistance or risk of diabetes in a subject taking a statin. The invention also provides compositions, methods and uses for reducing or decreasing increases in blood glucose caused by a statin in a subject taking a statin. The invention further provides compositions, methods and uses for reducing insulin resistance or risk of diabetes in a subject taking statins, and for treating diabetes in a subject taking statins. The invention moreover provides compositions, including an adenosine receptor antagonist, and/or an A2B receptor antagonist, and/or a CD73 antagonist and a statin.
• 1-Alkyl-8-(piperazine-1-sulfonyl)phenylxanthines: Development and Characterization of Adenosine A_2B Receptor Antagonists and a New Radioligand with Subnanomolar Affinity and Subtype Specificity
  作者：Thomas Borrmann、Sonja Hinz、Daniela C. G. Bertarelli、Wenjin Li、Nicole C. Florin、Anja B. Scheiff、Christa E. Müller

  DOI：10.1021/jm900413e

  日期：2009.7.9

  A new series of 1-alkyl-8-(piperazine-1-sulfonyl)phenylxanthines was designed, synthesized, and characterized in radioligand binding and functional assays at A(2B) adenosine receptors. A(2B) antagonists with subnanomolar affinity and high selectivity were discovered. The most potent compounds were 1-ethyl-8-(4-(4-(4-trifluoromethylbenzyl)piperazine-1-sulfonyl)phenyl)xanthine (24, PSB-09120, K-i (human A(2B)) = 0. 157 nM) and 8-(4-(4-(4-chlorobenzyl)piperazine-1-sulfonyl)phenyl)-1-propylxanthine (17, PSB-0788, K-i (human A2(B)) = 0.393 nM). Moreover, 8-(4-(4-(4-chlorophenyl)piperazine-1-sulfonyl)phenyl)-1-propylxanthine (35, PSB-603) was developed as an A(2B)-specific antagonist exhibiting a Ki value of 0.553 nM at the human A2B receptor and virtually no affinity for the human and rat A(1) and A(2A) and the human A(3) receptors up to a concentration of 10 mu M. A tritiated form of the compound was prepared as a new radioligand and characterized in kinetic, saturation, and competition studies. It was shown to be a useful pharmacological tool for the selective labeling of human as well as rodent A(2B) receptors (K-D human A(2B) 0.403 nM, mouse A(2B) 0.351 nM).