(R)-N-(2,3-二氢-1H-茚基)腺苷 | 96392-15-3

• 物质功能分类: 生物化工 - 核酸类
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: (R)-N-(2,3-二氢-1H-茚基)腺苷
• 中文别名: N-[(1r)-2,3-二氢-1H-茚-1-基]-腺苷酸
• 英文名称: PD 11751
• 英文别名: (R)-N-(2,3-dihydro-1H-inden-1-yl) adenosine；N6-[1-(R)-indanyl]adenosine；(R)-N-(2,3-Dihydro-1H-indenyl)adenosine；(2R,3R,4S,5R)-2-[6-[[(1R)-2,3-dihydro-1H-inden-1-yl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 96392-15-3
• 化学式: C₁₉H₂₁N₅O₄
• 分子量: 383.407
• InChiKey: FSKMJUWPFLDDRS-BYMDKACISA-N

物化性质

• 溶解度：
  DMF：10mg/mL； DMF:PBS (pH 7.2) (1:4)：0.2mg/mL；二甲基亚砜：5mg/mL；乙醇：0.1mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (R)-(-)-1-氨基茚满 、 6-氯嘌呤核苷 在 三乙胺 作用下， 以40%的产率得到(R)-N-(2,3-二氢-1H-茚基)腺苷
  参考文献：
  名称：

  Process for the resolution of 1-aminoindanes

  摘要：

  本文描述了一种改进的工艺，用于大规模地将1-氨基茚烷分离为R-异构体。该工艺中使用的分离剂是R-N-乙酰基-3,4-二甲氧基苯丙氨酸。该工艺是制备某些腺苷及其药学上可接受的酸盐中间体的过程。这些腺苷具有理想的中枢神经系统和心血管活性，如抗精神病、镇静、降压和抗心绞痛作用。

  公开号：

  US04833273A1

文献信息

• Method of treating heart failure and medicaments therefor
  申请人：Warner-Lambert Company

  公开号：US04693996A1

  公开（公告）日：1987-09-15

  The present invention relates to a combination of selected cardiotonic agents with selected adenosine receptor agonist antihypertensive agents resulting in a synergistic increase in myocardial contractility and cardiac output thereby rendering such combinations useful in treating heart failure.

  本发明涉及选定的心力衰竭药物与选定的腺苷受体激动剂降压药物的组合，从而产生协同增加心肌收缩力和心输出量，因此这些组合在治疗心力衰竭方面是有用的。
• N6-(1- and 2-benzocycloalkyl) adenosines
  申请人：Warner-Lambert Company

  公开号：US04501735A1

  公开（公告）日：1985-02-26

  N.sup.6 -(1 and 2-Benzocycloalkyl)adenosines and pharmaceutically acceptable acid addition salts having highly desirable central nervous system and cardiovascular properties, process for their manufacture, pharmaceutical compositions and methods for using said compounds and compositions are described.

  本文描述了具有高度理想的中枢神经系统和心血管特性的N.sup.6-(1和2-苯并环烷基)腺苷和药学上可接受的酸盐加成物，其制造过程，制药组合物以及使用该化合物和组合物的方法。
• Use of N6-[(1,2-dihydro-1-acenaphthylenyl) methyl]-adenosine in the preparation of pharmaceutical compounds for treating congestive heart failure
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0266504A2

  公开（公告）日：1988-05-11

  This application refers to the use of N⁶-[(1,2-dihydro-1-­acenaphthylenyl)-methyl]adenosine or a pharmaceutically acceptable salt thereof for the preparation of pharmaceuticals for treating congestive heart failure.

  本申请涉及 N⁶-[(1,2-二氢-1-苊烯基)-甲基]腺苷或其药学上可接受的盐用于制备治疗充血性心力衰竭的药物。
• Dog coronary artery adenosine receptor. Structure of the N6-aryl subregion
  作者：Shozo Kusachi、Robert D. Thompson、Noboyuki Yamada、Daniel T. Daly、R. A. Olsson

  DOI：10.1021/jm00156a016

  日期：1986.6

  Previous structure-coronary vasoactivity correlations of the N6-alkyladenosine analogues of N6-[(R)-1-phenyl-2-propyl]adenosine, 1, support the hypothesis that the coronary artery A2 adenosine receptor contains an N6 region of specialized structure. The part of this receptor region that binds the 2-propyl moiety of 1 determines stereoselectivity and contributes to coronary vasoactivity. The present study uses 92 adenosine analogues containing an aryl group in the N6 substituent to test the hypothesis that the N6 receptor region contains an aryl subregion that binds the phenyl moiety of 1 and thereby contributes to its coronary vasoactivity. N6-Aralkyladenosines are often more potent than their alkyl congeners. Two methylene residues seem to provide optimum separation of the aryl group from N6. Among adenosines with semirigid N6 substituents, N6-[(1R,2S)-trans-2-phenylcyclohexyl]adenosine was uniquely active, evidence that when 1 occupies the receptor, the axis of the propyl C-1 to phenyl C-1 bond is nearly in the plane described by N6 and propyl C-1 and C-2. The torsion angle around this bond is unknown. Replacing the phenyl group of N6-2-phenethyladenosine with a thienyl or a 3-pyridyl group raises activity. The structure-activity relationships of the N6-(arylethyl)-, the N6-(arylmethyl)-, and the N6-phenyladenosines differ strinkingly from each other. Taken together, such results support the idea that the N6 region of the dog coronary artery A2 adenosine receptor includes an aryl subregion.
• N6-Substituted adenosine receptor agonists: potential antihypertensive agents
  作者：B. K. Trivedi、C. J. Blankley、J. A. Bristol、H. W. Hamilton、W. C. Patt、W. J. Kramer、S. A. Johnson、R. F. Bruns、D. M. Cohen、M. J. Ryan

  DOI：10.1021/jm00107a025

  日期：1991.3

  Adenosine is known to exert a wide range of pharmacological effects including hypotension. This effect of adenosine suggested that modified analogues of adenosine might provide useful antihypertensive agents. Thus, we prepared a series of novel N6-benzocycloalkyladenosines and studied their receptor binding and antihypertensive activity. The structure-activity relationship study shows that the adenosine analogues having the hydrophobic phenyl moiety one carbon away from the C6-nitrogen have modest affinity and selectivity for the A1 receptor, whereas those with the phenyl moiety two carbons away from the C6-nitrogen have excellent affinity and selectivity for the A1 receptor. Many of these analogues showed excellent antihypertensive activity with a wide range of effects on heart rate. There is no direct correlation between the receptor binding affinities and antihypertensive activity; however, it is more closely associated with A1 than A2 affinity. The bradycardic effect of these agonists seems to be due to the A1 affinity. From this set, compound 3 was further evaluated in secondary antihypertensive screens. It lowered the blood pressure dose dependently with effects lasting for over 20 h following administration of a 30 mg/kg dose. Compound 3 was also effective in lowering blood pressure in a renal hypertensive rat model. Thus, appropriately modified N6-substituted adenosines represent a novel class of antihypertensive agents.