2-(1-hexynyl)-8-(propylamino)adenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-(1-hexynyl)-8-(propylamino)adenosine
• 英文别名: 2-(1-Hexynyl)-8-propylaminoadenosine；(2R,3R,4S,5R)-2-[6-amino-2-hex-1-ynyl-8-(propylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• 化学式: C₁₉H₂₈N₆O₄
• 分子量: 404.469
• InChiKey: DCVLYHNVEFYISA-XKLVTHTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  152
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-碘腺苷 在 palladium dichloride copper(l) iodide 、 溴 、 sodium acetate 、 三乙胺 、 三苯基膦 作用下， 以 水 、 乙腈 为溶剂， 生成 2-(1-hexynyl)-8-(propylamino)adenosine
  参考文献：
  名称：

  2,8-Disubstituted adenosine derivatives as partial agonists for the adenosine A2A receptor

  摘要：

  Novel 2,8-disubstituted adenosine derivatives were synthesized in good overall yields starting from 2-iodoadenosine. Binding affinities were determined for rat adenosine A(1) and A(2A) receptors and human A(3) receptors. Some compounds displayed good adenosine A(2A) receptor affinities, with most of the 2-(I-hexynyl)- and 2-[(E)-1-hexenyl]-substituted derivatives having K-i values in the nanomolar range. Although the introduction of an 8-alkylamino substituents decreased the affinity for the adenosine A(2A) receptor somewhat, the selectivity for this receptor compared to A(3) was improved significantly. The 8-methylamino (12) and 8-propylamino (14) derivatives of 2-(1-hexynyl)adeno sine (3), showed reasonable A(2A) receptor affinities with Ki values of 115 and 82 nM, respectively, and were 49- and 26-fold selective for the adenosine A(2A) receptor compared to the A(3) receptor. The compounds were also evaluated for their ability to stimulate the cAMP production in CHO cells expressing the human adenosine A(2A) receptor. 2-(I-Hexynyl)adenosine (3) and 2-[(E)-1-hexenyl]adenosine (4) both showed submaximal levels of produced cAMP, compared to the reference full agonist CGS 21680, and thus behaved as partial agonists. Most 8-alkylamino-substituted derivatives of 3, displayed similar cAMP production as 3, and behaved as partial agonists as well. Introduction of alkylamino groups at the 8-position of 4, showed a slight reduction of the efficacy compared to 4, and these compounds were partial agonists also. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00123-8

文献信息

• C2, 8-disubstituted adenosine derivatives and their different uses
  申请人：——

  公开号：US20040116374A1

  公开（公告）日：2004-06-17

  Novel C2, 8-disubstituted adenosine derivatives disclosed herein have been found to be potent adenosine receptor agonists, in particular for the A2A receptor. The said compounds have biological activity against conditions such as hypertension, ischemic heart disease, ischemic brain disease, psychosis and wound healing. Further, the invention also discloses a process for the preparation of such compounds and pharmaceutical compositions comprising them.

  本发明公开了 Novel C2，8-二取代腺苷衍生物，发现其是有效的腺苷受体激动剂，特别是对于A2A受体。所述化合物对高血压、缺血性心脏病、缺血性脑病、精神病和伤口愈合等疾病具有生物活性。此外，本发明还公开了制备这些化合物的方法和包含它们的药物组合物。
• C2,8-disubstituted adenosine derivatives and their different uses
  申请人：Universiteit Leiden

  公开号：US07112574B2

  公开（公告）日：2006-09-26

  Novel C2,8-disubstituted adenosine derivatives disclosed herein have been found to be potent adenosine receptor agonists, in particular for the A2A receptor. The said compounds have biological activity against conditions such as hypertension, ischemic heart disease, ischemic brain disease, psychosis and wound healing. Further, the invention also discloses a process for the preparation of such compounds and pharmaceutical compositions comprising them.

  本发明披露的新型C2,8-二取代腺苷衍生物被发现是有效的腺苷受体激动剂，特别是对于A2A受体。该化合物对高血压、缺血性心脏病、缺血性脑病、精神病和伤口愈合等疾病具有生物活性。此外，本发明还披露了一种制备这种化合物的方法和包含它们的制药组合物。
• C2, 8-DISUBSTITUTED ADENOSINE DERIVATIVES AND THEIR DIFFERENT USES
  申请人：Universiteit Leiden

  公开号：EP1368364A1

  公开（公告）日：2003-12-10
• US7112574B2
  申请人：——

  公开号：US7112574B2

  公开（公告）日：2006-09-26
• [EN] C2, 8-DISUBSTITUTED ADENOSINE DERIVATIVES AND THEIR DIFFERENT USES<br/>[FR] DERIVES D'ADENOSINE DISUBSTITUES C2, 8 ET LEURS DIVERSES UTILISATIONS
  申请人：UNIV LEIDEN

  公开号：WO2002070534A1

  公开（公告）日：2002-09-12

  The present invention pertains to novel C2,8-disubstituted adenosine derivatives, which are found to be potent adenosine receptor agonist, particularly for the A2A receptor. Further provided by the invention is a process for the preparation of such adenosine derivatives and pharmaceutical compositions comprising said compounds.