1,3-di-n-butyl-2-thioxanthine | 77038-96-1

• 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: 1,3-di-n-butyl-2-thioxanthine
• 英文别名: 1,3-di-n-butyl-2-thio-xanthine；1,3-dibutyl-2-sulfanylidene-7H-purin-6-one
• CAS: 77038-96-1
• 化学式: C₁₃H₂₀N₄OS
• 分子量: 280.394
• InChiKey: JMUNGAUERFBBQE-UHFFFAOYSA-N

物化性质

• 沸点：
  479.1±37.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  84.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-di-n-butyl-2-thioxanthine 在 三氯硅烷 、 氨 、 potassium nonaflate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 40.5h， 生成 1,3-di-n-butyl-2-thioxanthine 7-β-D-ribofuranoside
  参考文献：
  名称：

  Selective Ligands for Rat A3 Adenosine Receptors: Structure-Activity Relationships of 1,3-Dialkylxanthine 7-Riboside Derivatives

  摘要：

  1,3-Dibutylxanthine 7-riboside has been found to be a partial agonist at A(3) adenosine receptors (van Galen et al. Mol. Pharmacol. 1994, 45, 1101-1111). 1,3-Dialkylxanthine 7-riboside analogues modified at the 1-, 3-, and 8-purine positions and at the ribose 5'-position were synthesized. The nucleoside analogues were examined for affinity in radioligand binding assays at rat brain A(3) adenosine receptors stably expressed in CHO cells, using the radioligand [[I-125]-4-amino- 3-iodobenzyl]adenosine-5'-N-methyluronamide (AB-MECA). Affinity was assayed at rat brain A(1) and A(2a) receptors using [H-3]PIA and [H-3]CGS 21680, respectively. The affinity of xanthine 7-ribosides at A(3) receptors depended on the 1,3-dialkyl substituents in the order: Pent greater than or equal to. Bu >> Hx > Pr approximate to Me. 1,3-Dipentylxanthine 7-riboside was slightly selective for A(3) receptors (2-fold vs A(1) and 10-fold vs A(2a)). 8-Methoxy substitution was tolerated at A(3) receptors. 2-Thio vs 2-oxo substitution increased potency at all three subtypes and slightly increased A(3) vs A(1) selectivity. The 5'-uronamide modification, which was previously found to enhance A(3) selectivity in N-6-benzyladenosine derivatives, was also incorporated into the xanthine 7-ribosides, with similar results. The affinity of 1,3-dialkylxanthine 7-riboside 5'-uronamides at A(3) receptors depended on the N-alkyluronamide substituent in the order: MeNH > EtNH >> NH2 >> Me(2)N. Affinity of the 5'-uronamides at A(3) receptors was dependent on the 1,3-dialkyl substitution in the order: Bu > Pent > Hex. 1,3-Dibutylxanthine 7-riboside 5'-N-methylcarboxamide, with a K-i value of 229 nM at A(3) receptors, was 160-fold selective for rat A(3) vs A(1) receptors and > 400-fold selective vs A(2a) receptors. This derivative acted as a full agonist in the A(3) receptor-mediated inhibition of adenylate cyclase.

  DOI：

  10.1021/jm00049a021

文献信息

• Xanthine derivatives and their use in pharmaceutical compositions
  申请人：Wuelfing; Johann A.

  公开号：US04454138A1

  公开（公告）日：1984-06-12

  Compounds of the formula (II): ##STR1## wherein: X is sulphur and Y is oxygen or sulphur; R.sub.1 is an alkyl group of up to 6 carbon atoms; R.sub.2 is an alkyl group of up to 6 carbon atoms; and n is 1; or X is oxygen and Y is sulphur; one of R.sub.1 and R.sub.2 is an alkyl group of up to 6 carbon atoms and the other is an alkyl group of 2 to 6 carbon atoms; and n is 1 or 2, having useful pharmacological activity, pro-drugs therefor, a process for their preparation, pharmaceutical compositions containing said compounds or pro-drugs, and intermediates in their preparation of the compounds.

  式（II）的化合物：其中：X为硫，Y为氧或硫；R.sub.1为最多6个碳原子的烷基基团；R.sub.2为最多6个碳原子的烷基基团；n为1；或者X为氧，Y为硫；R.sub.1和R.sub.2中的一个是最多6个碳原子的烷基基团，另一个是2到6个碳原子的烷基基团；n为1或2，具有有用的药理活性，它们的前药，其制备方法，含有所述化合物或前药的药物组合物，以及制备所述化合物的中间体。
• A3 adenosine receptor agonists
  申请人：The United States of America as represented by the Department of Health

  公开号：US05773423A1

  公开（公告）日：1998-06-30

  The present invention provides N.sup.6 -benzyladenosine-5'-N-uronamide and related substituted compounds, particularly those containing substituents on the benzyl and/or uronamide groups, and modified xanthine ribosides, as well as pharmaceutical compositions containing such compounds. The present invention also provides a method of selectively activating an A.sub.3 adenosine receptor in a mammal, which method comprises acutely or chronically administering to a mammal in need of selective activation of its A.sub.3 adenosine receptor a therapeutically effective amount of a compound which binds with the A.sub.3 receptor so as to stimulate an A.sub.3 receptor-dependent response.

  本发明提供了N.sup.6-苄基腺苷-5'-N-醛脲和相关的取代化合物，特别是那些在苄基和/或醛脲基团上含有取代基的化合物，以及修饰的黄嘌呤核糖苷，以及含有这些化合物的药物组合物。本发明还提供了一种在哺乳动物中选择性激活A.sub.3腺苷受体的方法，该方法包括向需要选择性激活其A.sub.3腺苷受体的哺乳动物急性或慢性地给予与A.sub.3受体结合的化合物的治疗有效量，以刺激A.sub.3受体依赖的反应。
• Xanthine derivatives, a process for their preparation and their use in pharmaceutical compositions
  申请人：BEECHAM - WUELFING GmbH & Co. KG

  公开号：EP0018136B1

  公开（公告）日：1983-11-16
• A 3 ADENOSINE RECEPTOR AGONISTS
  申请人：THE UNITED STATES OF AMERICA, as represented by the Secretary of the Department of Health and Human Services

  公开号：EP0708781A1

  公开（公告）日：1996-05-01
• US4454138A
  申请人：——

  公开号：US4454138A

  公开（公告）日：1984-06-12