1-methyl-3-isobutyl-8-bromoxanthine | 63908-35-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1-methyl-3-isobutyl-8-bromoxanthine
• 英文别名: 1-Methyl-3-isobutyl-8-bromxanthin；8-bromo-3-isobutyl-1-methyl-3,7(9)-dihydro-purine-2,6-dione；8-Bromo-3-isobutyl-1-methyl-3,7-dihydro-purine-2,6-dione；8-bromo-1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
• CAS: 63908-35-0
• 化学式: C₁₀H₁₃BrN₄O₂
• 分子量: 301.143
• InChiKey: JCAIYNMCEMWPAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-3-isobutyl-8-bromoxanthine 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-Benzyl-8-(cyclopentylamino)-1-methyl-3-(2-methylpropyl)purine-2,6-dione
  参考文献：
  名称：

  Design and synthesis of xanthine analogues as potent and selective PDE5 inhibitors

  摘要：

  We have discovered potent and selective xanthine PDE5 inhibitors. Compound 25 (PDE5 IC50 = 0.6 nM, PDE6/PDE5 = 101) demonstrated similar functional efficacy and PK profile to Sildenafil (PDE5 IC50 = 3.5 nM, PDE6/PDE5 = 7). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00646-7
• 作为产物：
  描述：

  7-benzyl-1-methyl-3,7-dihydro-purine-2,6-dione 在 palladium dihydroxide 、 溴 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-methyl-3-isobutyl-8-bromoxanthine
  参考文献：
  名称：

  Design and synthesis of xanthine analogues as potent and selective PDE5 inhibitors

  摘要：

  We have discovered potent and selective xanthine PDE5 inhibitors. Compound 25 (PDE5 IC50 = 0.6 nM, PDE6/PDE5 = 101) demonstrated similar functional efficacy and PK profile to Sildenafil (PDE5 IC50 = 3.5 nM, PDE6/PDE5 = 7). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00646-7

文献信息

• Selective antagonists of A2B adenosine receptors
  申请人：Vanderbilt University

  公开号：US20030087904A1

  公开（公告）日：2003-05-08

  A compound of the following formula: 1 wherein R is an aliphatic or cycloaliphatic amine group or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable salt thereof. The compounds of formula (I) may be used to treat, among other indications, asthma and diarrhea.

  下式化合物 1 其中 R 是脂族或环脂族胺基或其药学上可接受的盐及其药学上可接受的盐。式（I）化合物可用于治疗哮喘和腹泻等疾病。
• Inhibition of separated forms of cyclic nucleotide phosphodiesterase from pig coronary arteries by 1,3-disubstituted and 1,3,8-trisubstituted xanthines
  作者：Jack N. Wells、John E. Garst、George L. Kramer

  DOI：10.1021/jm00140a008

  日期：1981.8

  A series of xanthines with varied substituents in the 1, 3, and 8 positions were prepared in an attempt to understand the structure--activity relationship for alkylxanthines as inhibitors of two different forms of cyclic nucleotide phosphodiesterase. Polar substituents on the 1 or 3 position of the xanthine reduced the potency of the xanthines to inhibit both the calmodulin-sensitive and the "cyclic AMP specific" forms of phosphodiesterase. Polar substituents on the 8 position of the xanthine, other than a carboxylic acid, increased the potency to inhibit the calmodulin-sensitive form of phosphodiesterase, if they were capable of donating electrons to the xanthine nucleus. On the other hand, any substituent in the 8 position larger than H reduced the potency of the xanthines to inhibit the cyclic AMP specific form of phosphodiesterase. Topographical maps of the active sites of the two forms of phosphodiesterase are presented in summary.
• FAVIER, C.;PINHAS, H.;BERANGER, S.;PASCAL, J. -C.
  作者：FAVIER, C.、PINHAS, H.、BERANGER, S.、PASCAL, J. -C.

  DOI：——

  日期：——
• SELECTIVE ANTAGONISTS OF A2B ADENOSINE RECEPTORS
  申请人：VANDERBILT UNIVERSITY

  公开号：EP1208100A1

  公开（公告）日：2002-05-29
• US6806270B2
  申请人：——

  公开号：US6806270B2

  公开（公告）日：2004-10-19