2-chloro-N⁶-cyclopentyl-9-methyladenine | 135394-16-0

• 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: 2-chloro-N⁶-cyclopentyl-9-methyladenine
• 英文别名: (2-Chloro-9-methyl-9H-purin-6-yl)-cyclopentyl-amine；2-chloro-N-cyclopentyl-9-methylpurin-6-amine
• CAS: 135394-16-0
• 化学式: C₁₁H₁₄ClN₅
• 分子量: 251.719
• InChiKey: POGDPKCNXXTDJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,6-二氯嘌呤 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 丙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2-chloro-N⁶-cyclopentyl-9-methyladenine
  参考文献：
  名称：

  N6,9-Disubstituted adenines: potent, selective antagonists at the A1 adenosine receptor

  摘要：

  N6-Substituted 9-methyladenines are potent antagonists of the activation of A1 adenosine receptors. The present study assessed the effect of N6 and N-9 substituents on the binding of adenines to the A1 and A2 receptors, respectively, of rat brain cortex and striatum and also on the antagonism of the A2 receptor mediated stimulation of the adenylate cyclase of PC12 cells by N-ethyladenosine-5'-uronamide. The potency ranking of 9-substituted adenines varied directly with the hydrophobicity of the substituent: cyclopentyl > phenyl > tetrahydrofuryl > methyl > 2-hydroxyethyl. The 9-substituted adenines showed little selectivity for either receptor and the R enantiomer of N6-(1-phenyl-2-propyl)-9-methyladenine was only 4-fold more potent than the S enantiomer at the A1 receptor. An N6-cyclopentyl substituent increased potency at the A1 receptor and decreased potency at the A2 receptor, resulting in selectivity for the A1 receptor of up to 39-fold. The N6-cyclophenyl group completely overshadowed the effect of the hydrophobicity of the 9-substituent. A 2-chloro substituent did not alter the potency of an N6-substituted 9-methyladenine.

  DOI：

  10.1021/jm00113a029

文献信息

• N?6 -SUBSTITUTED 9-METHYLADENINES: A NEW CLASS OF ADENOSINE RECEPTOR ANTAGONISTS
  申请人：Whitby Research Incorporated

  公开号：EP0457773A1

  公开（公告）日：1991-11-27
• EP0457773A4
  申请人：——

  公开号：EP0457773A4

  公开（公告）日：1993-03-10
• [EN] N<6>-SUBSTITUTED 9-METHYLADENINES: A NEW CLASS OF ADENOSINE RECEPTOR ANTAGONISTS
  申请人：WHITBY RESEARCH, INC.

  公开号：WO1990009178A1

  公开（公告）日：1990-08-23

  (EN) A series of N6-substituted adenines are disclosed to be antagonists of A2-adenosine receptor-mediated stimulation of adenylate cyclase in A2-adenosine receptors and antagonists of A1-adenosine receptor-mediated inhibition of adenylate cyclase. These compounds are useful in reversal of adenosine-mediated lipolysis, reversal of aenosine-mediated deleterious cardiovascular effects (conduction defects, hypotension), reversal of adenosine-mediated vascular actions in kidney, bronchodilation, antiarrhythmic action, reversal of adeno-mediated relaxation of smooth muscle, anti-narcoleptic action, CNS stimulation, and blockade of adenosine mediated inhibition of neurotransmitter release.(FR) Une série d'adénines substituées en position N6 servent d'antagonistes de la stimulation de la cyclase d'adénylate des récepteurs d'A2-adénosine dans les récepteurs d'A2-adénosine et d'antagonistes de l'inhibition de la cyclase d'adénylate par des récepteurs d'A1-adénosine. Ces composés sont utiles pour renverser la lipolyse par l'intermédiaire l'adénosine, les effets cardiovasculaires délétères provoqués par l'adénosine (défauts de conduction, hypotension), les actions vasculaires provoquées par l'adénosine dans les reins, la bronchodilatation, l'action antiarythmique, la relaxation par l'adénosine des muscles lisses, l'action antinarcoleptique, la stimulation de CNS, et le blocage de l'inhibition par l'adénosine de la libération de neuro-émetteurs.
• N6,9-Disubstituted adenines: potent, selective antagonists at the A1 adenosine receptor
  作者：Robert D. Thompson、Sherrie Secunda、John W. Daly、Ray A. Olsson

  DOI：10.1021/jm00113a029

  日期：1991.9

  N6-Substituted 9-methyladenines are potent antagonists of the activation of A1 adenosine receptors. The present study assessed the effect of N6 and N-9 substituents on the binding of adenines to the A1 and A2 receptors, respectively, of rat brain cortex and striatum and also on the antagonism of the A2 receptor mediated stimulation of the adenylate cyclase of PC12 cells by N-ethyladenosine-5'-uronamide. The potency ranking of 9-substituted adenines varied directly with the hydrophobicity of the substituent: cyclopentyl > phenyl > tetrahydrofuryl > methyl > 2-hydroxyethyl. The 9-substituted adenines showed little selectivity for either receptor and the R enantiomer of N6-(1-phenyl-2-propyl)-9-methyladenine was only 4-fold more potent than the S enantiomer at the A1 receptor. An N6-cyclopentyl substituent increased potency at the A1 receptor and decreased potency at the A2 receptor, resulting in selectivity for the A1 receptor of up to 39-fold. The N6-cyclophenyl group completely overshadowed the effect of the hydrophobicity of the 9-substituent. A 2-chloro substituent did not alter the potency of an N6-substituted 9-methyladenine.