8-cyclopentyl-1-methyl-3-propylxanthine | 132940-36-4

• 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: 8-cyclopentyl-1-methyl-3-propylxanthine
• 英文别名: 8-Cyclopentyl-1-methyl-3-propyl-3,7-dihydro-purine-2,6-dione；8-cyclopentyl-1-methyl-3-propyl-7H-purine-2,6-dione
• CAS: 132940-36-4
• 化学式: C₁₄H₂₀N₄O₂
• 分子量: 276.338
• InChiKey: JRLIUMNSBXRALC-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C
• 沸点：
  521.8±42.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环戊基甲酰氯 在 吡啶 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.25h， 生成 8-cyclopentyl-1-methyl-3-propylxanthine
  参考文献：
  名称：

  1,3,8-三取代的黄嘌呤。取代模式对腺苷受体A1 / A2亲和力的影响。

  摘要：

  一系列11个8-取代的黄嘌呤，在1和3位上具有三个不同的取代模式（模式a（R1 = R3 = CH2CH2CH3），b（R1 = CH2CH2CH3，R3 = CH3）和c（R1 = CH3，制备R 3 ＝ CH 2 CH 2 CH 3）]。评估这些化合物与腺苷A1和A2受体结合的亲和力和选择性。在A1受体上具有最大亲和力的化合物具有1,3取代模式a。除了一个例外，具有模式a的化合物在A2受体上的结合力也最强。但是，几种具有模式c的化合物在A2受体上与那些具有模式a的化合物等价。此外，这些8取代的黄嘌呤的1和3位上的取代基对于确定与A1受体的最大亲和力同样重要，而3位的取代基比1位的取代基对A2受体的效力更重要。结果，可以通过选择1-位和3-位取代基来最大化对A1受体的选择性。然而，以最大的A1选择性所需要的R1 / R3取代模式也以不完全理解的方式取决于8位的取代基。

  DOI：

  10.1021/jm00108a029

文献信息

• A₁ Adenosine Receptor Antagonists as Ligands for Positron Emission Tomography (PET) and Single-Photon Emission Tomography (SPET)
  作者：Marcus H. Holschbach、Thomas Fein、Christof Krummeich、Robert G. Lewis、Walter Wutz、Ulrich Schwabe、Dieter Unterlugauer、Ray A. Olsson

  DOI：10.1021/jm9705465

  日期：1998.2.1

  The high affinity of 8-cyclopentyl-1,3-dipropylxanthine (CPX) for the A(1) adenosine receptor (A(1)AR) provides a good lead for developing radioligands suitable for positron emission tomography (PET) and single-photon emission tomography (SPET). This study tested the hypothesis that the kinds of chemical modifications made in the synthesis of CPX analogues containing carbon-ii, fluorine-18, or radioiodine will not alter affinity for the A(1)AR. This report describes the synthesis and radioligand binding assays of unlabeled CPX analogues having methyl, 2-methoxyethyl, 2-fluoropropyl, or 3-fluoropropyl substituents, respectively, at either N-1 (13a-d) or N-3 (8a-d) or an (E)-3-iodoprop-2-en-1-yl substituent at N-3 (8f). Compounds 8d,f and 13b,d antagonized the binding of [H-3]CPX to the A(1)AR of rat brain with affinities similar to those of CPX; compound 8c was twice as potent as CPX. Analogues 8a,b and 13a were less potent than CPX, but for each the K-i of antagonism was greater than or equal to 0.5 nM. Attempts to iodinate the 8-(4-hydroxyphenyl) analogue of CPX failed, probably because the xanthine substituent strongly deactivated the phenol toward electrophilic iodination. In summary, several of the modifications of the propyl groups of CPX needed to produce ligands for imaging by PET and SPET preserve or enhance affinity for the A(1)AR.
• ERICKSON, RONALD H.;HINER, ROGER N.;FEENEY, SCOTT W.;BLAKE, PAUL R.;RZESZ+, J. MED. CHEM., 34,(1991) N, C. 1431-1435
  作者：ERICKSON, RONALD H.、HINER, ROGER N.、FEENEY, SCOTT W.、BLAKE, PAUL R.、RZESZ+

  DOI：——

  日期：——
• ADENOSINE RECEPTOR AGONISTS FOR THE TREATMENT AND PREVENTION OF VASCULAR OR JOINT CAPSULE CALCIFICATION DISORDERS
  申请人：Gahl William A.

  公开号：US20130109645A1

  公开（公告）日：2013-05-02

  Disclosed are a method of treating or preventing a disorder in a mammal comprising administering to the mammal an adenosine receptor agonist or an adenosine receptor antagonist, either alone or in combination, in an amount effective to treat or prevent medial vascular or joint capsule calcification. Disclosed are methods of detecting or diagnosing a vascular or joint capsule calcification disorder, as well as a nucleic acid comprising a mutation in one or more exons of human NT5E selected from the group consisting of Exon 3, Exon 5, and Exon 9.
• 1,3,8-Trisubstituted xanthines. Effects of substitution pattern upon adenosine receptor A1/A2 affinity
  作者：Ronald H. Erickson、Roger N. Hiner、Scott W. Feeney、Paul R. Blake、Waclaw J. Rzeszotarski、Rickey P. Hicks、Diane G. Costello、Mary E. Abreu

  DOI：10.1021/jm00108a029

  日期：1991.4

  8-substituted xanthines were equally important for determining maximum affinity to the A1 receptor, while the substituent at the 3-position is more important than the substituent at the 1-position for potency at the A2 receptor. As a result of this, it is possible to maximize selectivity for the A1 receptor by choice of the 1- and 3-position substituents. However, the R1/R3 substitution pattern required

  一系列11个8-取代的黄嘌呤，在1和3位上具有三个不同的取代模式（模式a（R1 = R3 = CH2CH2CH3），b（R1 = CH2CH2CH3，R3 = CH3）和c（R1 = CH3，制备R 3 ＝ CH 2 CH 2 CH 3）]。评估这些化合物与腺苷A1和A2受体结合的亲和力和选择性。在A1受体上具有最大亲和力的化合物具有1,3取代模式a。除了一个例外，具有模式a的化合物在A2受体上的结合力也最强。但是，几种具有模式c的化合物在A2受体上与那些具有模式a的化合物等价。此外，这些8取代的黄嘌呤的1和3位上的取代基对于确定与A1受体的最大亲和力同样重要，而3位的取代基比1位的取代基对A2受体的效力更重要。结果，可以通过选择1-位和3-位取代基来最大化对A1受体的选择性。然而，以最大的A1选择性所需要的R1 / R3取代模式也以不完全理解的方式取决于8位的取代基。