2-(2-cyclopentyl-1-ethyn-1-yl)adenosine | 141345-09-7

• 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-(2-cyclopentyl-1-ethyn-1-yl)adenosine
• 英文别名: Adenosine, 2-(cyclopentylethynyl)-；(2R,3R,4S,5R)-2-[6-amino-2-(2-cyclopentylethynyl)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 141345-09-7
• 化学式: C₁₇H₂₁N₅O₄
• 分子量: 359.385
• InChiKey: RKZIPCGIVSAJHA-IWCJZZDYSA-N

物化性质

• 沸点：
  750.1±70.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 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',3',5'-三-O-乙酰-6-氯-2-碘嘌呤核苷 在 bis-triphenylphosphine-palladium(II) chloride 、 ammonium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 21.0h， 生成 2-(2-cyclopentyl-1-ethyn-1-yl)adenosine
  参考文献：
  名称：

  Nucleosides and nucleotides. 107. 2-(Cycloalkylalkynyl)adenosines: adenosine A2 receptor agonists with potent antihypertensive effects

  摘要：

  Adenosine receptor-binding profiles in rat brain tissues and antihypertensive effects in spontaneously hypertensive rats (SHR) of a series of 2-(cycloalkylalkynyl)adenosines (2-CAAs) and their congeners are described. The structure-activity relationship of this series of compounds is discussed, focusing on the length of the alkynyl side chain and bulkiness of the terminal cycloalkyl substituents in terms of binding activity and cardiovascular effects. All the 2-CAAs had a preferential affinity for A2 receptors. Of these derivatives, 2-(3-cyclopentyl-1-propyn-1-yl)adenosine (10b) exhibited the most selective affinity for A2 receptors (K(i) ratio: A1/A2 = 70) on the basis of receptor binding. In the C-2 binding region of adenosine, compounds often have potent and/or selective A2 activity from introduction of an acetylenic group at the C-2 position followed by one methylene residue further followed by a hydrophobic substituent such as a cycloalkyl ring at the terminal position of the alkynyl side chain. Intravenous injection of 10b up to 100-mu-g/kg had a potent hypotensive effect without a marked decrease in heart rate in anesthetized SHR. Compounds 10j-s, with a hydroxyl group in the C-3" position of the alkynyl side chain, had a potent affinity for both A1 and A2 receptors, but they were not highly selective for A2 receptors. These compounds caused a marked bradycardia upon intravenous administration in anesthetized SHR. Oral administration of 10b (0.1-1 mg/kg) had a potent and long-lasting antihypertensive effect in conscious SHR.

  DOI：

  10.1021/jm00090a017

文献信息

• Adenosine derivatives and use thereof
  申请人：Konno Takashi

  公开号：US20050130930A1

  公开（公告）日：2005-06-16

  2-(6-Cyano-1-hexyn-1-yl)adenosine, 2-(6-cyano-1-hexyn-1-yl)adenosine 5′-monophosphate, or salts thereof; and drugs containing the same as an active ingredient. The compounds have excellent effects of lowering ocular tension, promoting blood flow in retina, and protecting optic nerve failure and are highly soluble in water. Owing to these characteristics, the compounds are useful as drugs such as remedies for glaucoma and ocular hypertension.

  2-(6-氰基-1-己炔-1-基)腺苷、2-(6-氰基-1-己炔-1-基)腺苷5'-磷酸或其盐；以及含有其作为活性成分的药物。这些化合物具有降低眼压、促进视网膜血流、保护视神经功能失调的优异效果，并且在水中高度溶解。由于这些特性，这些化合物可用作药物，例如治疗青光眼和眼内压的药物。
• MEDICINAL COMPOSITIONS FOR TREATING EYE DISEASES
  申请人：YAMASA CORPORATION

  公开号：EP1110554A1

  公开（公告）日：2001-06-27

  Medicinal compositions for treating eye diseases which contain as the active ingredient 2-alkynyladenosine derivatives having an acetylene union at the 2-position of adenine base. Having a long-lasting and remarkable effect of lowering ocular tension, these compositions are useful as remedies for eye diseases accompanying increased ocular tension or optic nerve failures, such as glaucoma and hypertonia oculi.

  治疗眼疾的药物组合物，其活性成分为腺嘌呤基 2 位上有乙炔结合的 2-炔基腺苷衍生物。这些复方制剂具有降低眼球张力的持久而显著的效果，可用于治疗伴有眼球张力增高或视神经衰竭的眼病，如青光眼和眼球过度紧张症。
• ADENOSINE DERIVATIVES AND USE THEREOF
  申请人：TOA EIYO LTD.

  公开号：EP1316559B1

  公开（公告）日：2004-11-03
• US6387889B1
  申请人：——

  公开号：US6387889B1

  公开（公告）日：2002-05-14
• US6936596B2
  申请人：——

  公开号：US6936596B2

  公开（公告）日：2005-08-30