2-[(E)-1-hexenyl]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-[(E)-1-hexenyl]adenosine
• 英文别名: (2R,3R,4S,5R)-2-[6-Amino-2-((E)-hex-1-enyl)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol；(2R,3R,4S,5R)-2-[6-amino-2-[(E)-hex-1-enyl]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• 化学式: C₁₆H₂₃N₅O₄
• 分子量: 349.39
• InChiKey: CGSZRCYBQDADPV-KBMGPZOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-[(E)-1-hexenyl]-1,3,2-benzodioxaborole 、 2-碘腺苷 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 生成 2-[(E)-1-hexenyl]adenosine
  参考文献：
  名称：

  2-Alkenyl and 2-Alkyl Derivatives of Adenosine and Adenosine-5‘-N-Ethyluronamide:  Different Affinity and Selectivity of E- and Z-Diastereomers at A_2A Adenosine Receptors

  摘要：

  A series of new 2-(ar)alkenyl, both Z- and E-diastereomers, and 2-alkyl derivatives of adenosine-5'-N-ethyluronamide (NECA) and adenosine were synthesized and evaluated for their interaction with the A(1) and A(2A) adenosine receptors, to better understand the conformational requirements of the receptor area interacting with the substituents in the 2- and 5'-positions. Partial reduction of the triple bond in 2-alkynyl derivatives of NECA led to compounds whose activity at the A(2A) receptor subtype was related to Z-E-isomerism, the E-diastereomers being more potent and selective than the Z-ones. Saturation of the side chain markedly reduced compound affinity at adenosine receptors. Specifically, compounds bearing an (E)-alkenyl chain, while maintaining the same affinity at A(2A) receptors as the corresponding alkynyl derivatives, showed an increase in A(2A) vs A(1) selectivity. Hence, the new nucleosides (E)-2-hexenylNECA (12a) and (E)-2-(phenylpenteny1)NECA (12b) exhibited both high A(2A) receptor affinity (K-i = 1.6 and 3.5 nM, respectively) and A(2A) VS A(1) selectivity (157- and 290-fold, respectively). Moreover, 12a displayed potent antiaggregatory activity, similar to that of the reference compound NECA. Comparison between NECA and adenosine derivatives further demonstrated that the 5'-ethylcarboxamido group is critical for the A(2A) affinity. These studies indicated that the orientation of the substituent in the 2-position and the nature of the 5'-group in adenosine derivatives are critical to achieve high affinity and selectivity at the A(2A) adenosine receptor subtype.

  DOI：

  10.1021/jm960376g

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。
• 2-Alkenyl and 2-Alkyl Derivatives of Adenosine and Adenosine-5‘-<i>N</i>-Ethyluronamide:  Different Affinity and Selectivity of <i>E</i>- and <i>Z</i>-Diastereomers at A_2A Adenosine Receptors
  作者：Sauro Vittori、Emidio Camaioni、Emanuela Di Francesco、Rosaria Volpini、Angela Monopoli、Silvio Dionisotti、Ennio Ongini、Gloria Cristalli

  DOI：10.1021/jm960376g

  日期：1996.1.1

  A series of new 2-(ar)alkenyl, both Z- and E-diastereomers, and 2-alkyl derivatives of adenosine-5'-N-ethyluronamide (NECA) and adenosine were synthesized and evaluated for their interaction with the A(1) and A(2A) adenosine receptors, to better understand the conformational requirements of the receptor area interacting with the substituents in the 2- and 5'-positions. Partial reduction of the triple bond in 2-alkynyl derivatives of NECA led to compounds whose activity at the A(2A) receptor subtype was related to Z-E-isomerism, the E-diastereomers being more potent and selective than the Z-ones. Saturation of the side chain markedly reduced compound affinity at adenosine receptors. Specifically, compounds bearing an (E)-alkenyl chain, while maintaining the same affinity at A(2A) receptors as the corresponding alkynyl derivatives, showed an increase in A(2A) vs A(1) selectivity. Hence, the new nucleosides (E)-2-hexenylNECA (12a) and (E)-2-(phenylpenteny1)NECA (12b) exhibited both high A(2A) receptor affinity (K-i = 1.6 and 3.5 nM, respectively) and A(2A) VS A(1) selectivity (157- and 290-fold, respectively). Moreover, 12a displayed potent antiaggregatory activity, similar to that of the reference compound NECA. Comparison between NECA and adenosine derivatives further demonstrated that the 5'-ethylcarboxamido group is critical for the A(2A) affinity. These studies indicated that the orientation of the substituent in the 2-position and the nature of the 5'-group in adenosine derivatives are critical to achieve high affinity and selectivity at the A(2A) adenosine receptor subtype.
• 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.