N⁶-cyclopentyl-5'-deoxy-5'-ethylthioadenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: N⁶-cyclopentyl-5'-deoxy-5'-ethylthioadenosine
• 英文别名: (2R,3R,4S,5S)-2-[6-(cyclopentylamino)purin-9-yl]-5-(ethylsulfanylmethyl)oxolane-3,4-diol
• 化学式: C₁₇H₂₅N₅O₃S
• 分子量: 379.483
• InChiKey: BPIKXQYCIFKGEK-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N6-cyclopentyl-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxy-5'-ethylthioadenosine 在 氟化铵 作用下， 以 甲醇 为溶剂， 以37%的产率得到N⁶-cyclopentyl-5'-deoxy-5'-ethylthioadenosine
  参考文献：
  名称：

  N6-substituted C5′-modified adenosines as A1 adenosine receptor agonists

  摘要：

  Adenosines bearing 5'-modification in conjunction with an N-6-substituent have previously been shown to act as partial agonists at the A(1) adenosine receptor. Our current work investigates the effect of modifying the 5'-position in conjunction with efficacious bicyclic and tricyclic N-6-substituents. Several highly potent agonists for the A(1) adenosine receptor were identified; however, all of these compounds behaved as full agonists. In keeping with previous reports, 5'-halogen and 5'-sulfide derivatives of N-6-(endo-norborn-2-yl) adenosine were, in general, low nanomolar agonists of the A(1) adenosine receptor. The known partial agonist, N-6-cyclopentyl-5'-deoxy-5'-ethylthioadenosine (2), also behaved as a full agonist in our assay. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.010

文献信息

• Van Der Wenden, Eleonora M.; Carnielli, Marta; Roelen, Harlof C. P. F., Journal of Medicinal Chemistry, 1998, vol. 41, # 1, p. 102 - 108
  作者：Van Der Wenden, Eleonora M.、Carnielli, Marta、Roelen, Harlof C. P. F.、Lorenzen, Anna、Künzel, Jacobien K.、Ijzerman, Adriaan P.

  DOI：——

  日期：——
• N6-substituted C5′-modified adenosines as A1 adenosine receptor agonists
  作者：T.D. Ashton、Stephen P. Baker、Sally A. Hutchinson、Peter J. Scammells

  DOI：10.1016/j.bmc.2007.11.010

  日期：2008.2.15

  Adenosines bearing 5'-modification in conjunction with an N-6-substituent have previously been shown to act as partial agonists at the A(1) adenosine receptor. Our current work investigates the effect of modifying the 5'-position in conjunction with efficacious bicyclic and tricyclic N-6-substituents. Several highly potent agonists for the A(1) adenosine receptor were identified; however, all of these compounds behaved as full agonists. In keeping with previous reports, 5'-halogen and 5'-sulfide derivatives of N-6-(endo-norborn-2-yl) adenosine were, in general, low nanomolar agonists of the A(1) adenosine receptor. The known partial agonist, N-6-cyclopentyl-5'-deoxy-5'-ethylthioadenosine (2), also behaved as a full agonist in our assay. (C) 2007 Elsevier Ltd. All rights reserved.