腺苷-5'-羧酸2-氯乙酯 | 41110-82-1

• 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: 腺苷-5'-羧酸2-氯乙酯
• 英文名称: adenosine-5'-carboxylic acid 2-chloroethyl ester
• 英文别名: adenosine-5'-(β-chloroethyl)carboxylate；1-(6-amino-purin-9-yl)-β-D-1-deoxy-ribofuranuronic acid 2-chloro-ethyl ester；Adenosin-5'-saeure-ss-chlorethylester；2-Chloraethyl-adenosin-5'-carboxylat；2-chloroethyl (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolane-2-carboxylate
• CAS: 41110-82-1
• 化学式: C₁₂H₁₄ClN₅O₅
• 分子量: 343.727
• InChiKey: AGNKIWHXJZQJIJ-MCHASIABSA-N

物化性质

• 沸点：
  687.0±65.0 °C(Predicted)
• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  5
• 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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  腺苷酸-5-羧酸	adenosine 5'-carboxylic acid	3415-09-6	C10H11N5O5	281.228

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-N-乙基酰胺基腺苷	5'-N-Ethylcarboxamidoadenosine	35920-39-9	C12H16N6O4	308.297
  ——	Adenosin-5'-carbonsaeue-N-(β-hydroxyethyl)-amid	35788-28-4	C12H16N6O5	324.296
  ——	Adenosin-5'-carbonsaeure-N-(2-dimethylaminoethyl)-amid	35788-31-9	C14H21N7O4	351.365
  ——	Adenosin-5'-carbonsaeure-N-allylamid	35788-26-2	C13H16N6O4	320.308
  ——	1-(6-amino-purin-9-yl)-β-D-1-deoxy-ribofuranuronic acid cyclopropylmethyl-amide	58048-25-2	C14H18N6O4	334.335
  ——	1-(6-amino-purin-9-yl)-β-D-1-deoxy-ribofuranuronic acid 2-diethylamino-ethylamide	58048-19-4	C16H25N7O4	379.419
  5-(N-环丙基)酰胺酰酐	5-(N-cyclopropyl)carboxamidoadenosine	50908-62-8	C13H16N6O4	320.308
  ——	(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-cyclobutyl-3,4-dihydroxytetrahydrofuran-2-carboxamide	55549-09-2	C14H18N6O4	334.335
  ——	1-(6-amino-purin-9-yl)-β-D-1-deoxy-ribofuranuronic acid 2-phenoxy-ethylamide	58048-18-3	C18H20N6O5	400.394
  ——	2',3'-di-O-acetyladenosine-5'-(N-rthyl)carboxamide	58048-26-3	C16H20N6O6	392.371

反应信息

• 作为反应物：
  描述：

  腺苷-5'-羧酸2-氯乙酯 在 palladium on activated charcoal 双氧水 、 溶剂黄146 作用下， 反应 2.5h， 生成 adenosine-5'-(N-cyclopropyl)carboxamide N¹-oxide
  参考文献：
  名称：

  嘌呤核苷5'位置的修饰。2.腺苷5′-（N-取代的）羧酰胺的合成和一些心血管性能。

  摘要：

  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。

  DOI：

  10.1021/jm00177a021
• 作为产物：
  描述：

  腺苷酸-5-羧酸 、 2-氯乙醇 在 氯化亚砜 作用下， 反应 60.0h， 以49%的产率得到腺苷-5'-羧酸2-氯乙酯
  参考文献：
  名称：

  Inactivation of S-Adenosyl-l-homocysteine Hydrolase by Amide and Ester Derivatives of Adenosine-5‘-carboxylic Acid

  摘要：

  S-Adenosyl-L-homocysteine (AdoHcy) hydrolase has been shown to have (5'/6') hydrolytic activity with vinyl (5') or homovinyl (6') halides derived from adenosine (Ado). This hydrolytic activity is independent of its 3'-oxidative activity. The vinyl (or homovinyl) halides are converted into 5'(or 6')-carboxaldehydes by the hydrolytic activity of the enzyme, and inactivation occurs via the oxidative activity. Amide and ester derivatives of Ado-5'-carboxylic acid were prepared to further probe the hydrolytic capability of AdoHcy hydrolase. The oxidative activity (but not the hydrolytic activity) is involved in the mechanism of inhibition of the enzyme by the ester and amide derivatives of Ado-5'-carboxylic acid, in contrast to the inactivation of this enzyme by adenosine-derived vinyl or homovinyl halide analogues during which both activities are manifested.

  DOI：

  10.1021/jm960313y

文献信息

• Inactivation of <i>S-</i>Adenosyl-<scp>l</scp>-homocysteine Hydrolase by Amide and Ester Derivatives of Adenosine-5‘-carboxylic Acid
  作者：Stanislaw F. Wnuk、Siming Liu、Chong-Sheng Yuan、Ronald T. Borchardt、Morris J. Robins

  DOI：10.1021/jm960313y

  日期：1996.1.1

  S-Adenosyl-L-homocysteine (AdoHcy) hydrolase has been shown to have (5'/6') hydrolytic activity with vinyl (5') or homovinyl (6') halides derived from adenosine (Ado). This hydrolytic activity is independent of its 3'-oxidative activity. The vinyl (or homovinyl) halides are converted into 5'(or 6')-carboxaldehydes by the hydrolytic activity of the enzyme, and inactivation occurs via the oxidative activity. Amide and ester derivatives of Ado-5'-carboxylic acid were prepared to further probe the hydrolytic capability of AdoHcy hydrolase. The oxidative activity (but not the hydrolytic activity) is involved in the mechanism of inhibition of the enzyme by the ester and amide derivatives of Ado-5'-carboxylic acid, in contrast to the inactivation of this enzyme by adenosine-derived vinyl or homovinyl halide analogues during which both activities are manifested.
• 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。