ethyl adenosine-5'-carboxylate | 35803-57-7

• 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: ethyl adenosine-5'-carboxylate
• 英文别名: ethyl adenosine-5'-uronate；1-(6-amino-purin-9-yl)-β-D-1-deoxy-ribofuranuronic acid ethyl ester；ethyl 1-(6-amino-9H-purin-9-yl)-1-deoxy-β-D-ribofuranuronate；Adenosin-5'-carbonsaeureaethylester；Adenosin-5'-carbonsaeureethylester；Aethyl-adenosin-5'-carboxylat；ethyl (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolane-2-carboxylate
• CAS: 35803-57-7
• 化学式: C₁₂H₁₅N₅O₅
• 分子量: 309.282
• InChiKey: IHTXJAFDKUQWOX-MCHASIABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl adenosine-5'-carboxylate 在 硼氘化钠 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以1.06 g的产率得到<5',5'-2H2>adenosine
  参考文献：
  名称：

  Mass spectrometry of nucleic acid constituents. Trimethylsilyl derivatives of nucleosides

  摘要：

  DOI：

  10.1021/jo00141a023
• 作为产物：
  描述：

  2',3'-isopropylideneadenosine-5'-carboxylic acid 在 盐酸 、 氯化亚砜 作用下， 反应 18.5h， 生成 ethyl adenosine-5'-carboxylate
  参考文献：
  名称：

  N6-Substituted N-alkyladenosine-5'-uronamides: bifunctional ligands having recognition groups for A1 and A2 adenosine receptors

  摘要：

  The coronary vasoactivity of N-ethyl-1'-deoxy-1'-(6-amino-9H-purin-9-yl)-beta-D-ribofuranuronamide (NECA, 1) is over 2 orders of magnitude greater than that of adenosine, and the vasoactivity of certain N6-substituted adenosines is as much as 1 order of magnitude greater. Such results suggest that a combination of appropriate modifications at N6 and C-5' might additively augment the agonist potency of adenosine. At low temperatures 1-deoxy-1-(6-chloro-9H-purin-9-yl)-2',3'-O-isopropylidene- beta-D-ribofuranosyl chloride (5), obtained in three steps from inosine, reacts with amines to yield uronamides. The subsequent reaction of such uronamides with amines at elevated temperatures displaces the purine 6-chloro group to yield, after deblocking, N-alkyl(or aryl)-N6-alk(ar)yl-adenosine-5'-uronamides. At the coronary artery A2 receptor the potency of N6-modified analogues of 1 is similar to that of the N6-substituted adenosine, rather than equal to or greater than 1. As agonists in the A2 receptor-mediated stimulation of adenylate cyclase in plasma membranes of PC12 pheochromocytoma cells or human platelets, N6-substituted analogues of 1 are intermediate between the high potency of 1 and the lower potency of the N6-substituted adenosines. At the A1 receptor of rat brain the potency of an N6-substituted analogue of 1 is often greater than that of the corresponding N6-substituted adenosine. At all four receptors, replacing the ethyl group of N-ethyl-N6-3-pentyladenosine-5'-uronamide by larger alkyl groups reduces potency; amides of secondary amines are inactive or have only marginal activity. Analogues of 1 containing a chiral center in the N6 substituent retain the stereoselectivity characteristic of each of the four receptors. Thus, at either A1 or A2 adenosine receptors, adenosine analogues interact with both the N6 and the C-5' receptor regions. However, the effects of N6 and C-5' modifications on potency are less than additive, evidence that the interaction of a substituent with its receptor region influences the interaction of other substituents with their respective receptor regions.

  DOI：

  10.1021/jm00159a020

文献信息

• Modification of the 5' position of purine nucleosides. 2. Synthesis and some cardiovascular properties of adenosine-5'-(N-substituted)carboxamides
  作者：Raj Nandan Prasad、Dilbagh S. Bariana、Anthony Fung、Milica Savic、Karin Tietje、Herman H. Stein、Harold Brondyk、Richard S. Egan

  DOI：10.1021/jm00177a021

  日期：1980.3

  of the esters of adenosine-5'-carboxylic acid, a systematic study of the corresponding amides (14--50) was undertaken. In addition, several other analogues containing the N1-oxide function (51--52) or 2',3' substituents (3--9, 53--54) were studied.

  先前我们已经表明，腺苷5'-羧酸酯（10）代表了一类新的有效的无毒冠状血管扩张剂。例如，在犬中通过十二指肠内或静脉内途径具有活性的乙酯（12）会导致冠状窦PO2和冠状动脉血流大量增加。由于腺苷5'-羧酸的酯具有明显的血管活性，因此对相应的酰胺（14--50）进行了系统的研究。此外，还研究了其他几种含有N1-氧化物官能团（51--52）或2'，3'取代基（3--9、53--54）的类似物。
• MEDICINAL COMPOSITION FOR PREVENTION OR TREATMENT OF HEPATOPATHY
  申请人：Nippon Shinyaku Co., Ltd.

  公开号：EP0983768A1

  公开（公告）日：2000-03-08

  A medicinal composition containing an adenosine A2 receptor agonist as the active ingredient. It is effective in the prevention or treatment of hepatopathy.

  一种以腺苷 A2 受体激动剂为活性成分的药物组合物。它可有效预防或治疗肝病。
• Timoshchuk, V. A., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 3.1, p. 427 - 441
  作者：Timoshchuk, V. A.

  DOI：——

  日期：——
• TIMOSHCHUK, V. A., ZH. ORGAN. XIMII, 26,(1990) N, S. 498-516
  作者：TIMOSHCHUK, V. A.

  DOI：——

  日期：——
• N6-Substituted N-alkyladenosine-5'-uronamides: bifunctional ligands having recognition groups for A1 and A2 adenosine receptors
  作者：R. A. Olsson、Shozo Kusachi、Robert D. Thompson、Dieter Ukena、William Padgett、John W. Daly

  DOI：10.1021/jm00159a020

  日期：1986.9

  The coronary vasoactivity of N-ethyl-1'-deoxy-1'-(6-amino-9H-purin-9-yl)-beta-D-ribofuranuronamide (NECA, 1) is over 2 orders of magnitude greater than that of adenosine, and the vasoactivity of certain N6-substituted adenosines is as much as 1 order of magnitude greater. Such results suggest that a combination of appropriate modifications at N6 and C-5' might additively augment the agonist potency of adenosine. At low temperatures 1-deoxy-1-(6-chloro-9H-purin-9-yl)-2',3'-O-isopropylidene- beta-D-ribofuranosyl chloride (5), obtained in three steps from inosine, reacts with amines to yield uronamides. The subsequent reaction of such uronamides with amines at elevated temperatures displaces the purine 6-chloro group to yield, after deblocking, N-alkyl(or aryl)-N6-alk(ar)yl-adenosine-5'-uronamides. At the coronary artery A2 receptor the potency of N6-modified analogues of 1 is similar to that of the N6-substituted adenosine, rather than equal to or greater than 1. As agonists in the A2 receptor-mediated stimulation of adenylate cyclase in plasma membranes of PC12 pheochromocytoma cells or human platelets, N6-substituted analogues of 1 are intermediate between the high potency of 1 and the lower potency of the N6-substituted adenosines. At the A1 receptor of rat brain the potency of an N6-substituted analogue of 1 is often greater than that of the corresponding N6-substituted adenosine. At all four receptors, replacing the ethyl group of N-ethyl-N6-3-pentyladenosine-5'-uronamide by larger alkyl groups reduces potency; amides of secondary amines are inactive or have only marginal activity. Analogues of 1 containing a chiral center in the N6 substituent retain the stereoselectivity characteristic of each of the four receptors. Thus, at either A1 or A2 adenosine receptors, adenosine analogues interact with both the N6 and the C-5' receptor regions. However, the effects of N6 and C-5' modifications on potency are less than additive, evidence that the interaction of a substituent with its receptor region influences the interaction of other substituents with their respective receptor regions.