N-乙酰基-6-氯-9-(2,3,5-三-O-乙酰基呋喃戊糖基)-9H-嘌呤-2-胺 | 137896-02-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: N-乙酰基-6-氯-9-(2,3,5-三-O-乙酰基呋喃戊糖基)-9H-嘌呤-2-胺
• 中文别名: 2-乙酰氨基-6-氯-9-(2,3,5-三-O-乙酰基Β-D-D-呋喃核糖基)嘌呤
• 英文名称: 2-acetamido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-chloropurine
• 英文别名: 6-chloro-2-acetamido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine；2-acetamide-6-chloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine；2-Acetamido-6-chloro-9-(2',3',5'-tri-O-acetyl-b-D-ribofuranosyl)purine；[(2R,3R,4R,5R)-5-(2-acetamido-6-chloropurin-9-yl)-3,4-diacetyloxyoxolan-2-yl]methyl acetate
• CAS: 137896-02-7
• 化学式: C₁₈H₂₀ClN₅O₈
• 分子量: 469.839
• InChiKey: OVXYEIBYTBNNFE-LSCFUAHRSA-N

物化性质

• 熔点：
  71-73°C
• 密度：
  1.63±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮、氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-乙酰基-6-氯-9-(2,3,5-三-O-乙酰基呋喃戊糖基)-9H-嘌呤-2-胺 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到2-acetamido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-azidopurine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹

  摘要：

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.

  DOI：

  10.1021/jo051256w
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以69%的产率得到N-乙酰基-6-氯-9-(2,3,5-三-O-乙酰基呋喃戊糖基)-9H-嘌呤-2-胺
  参考文献：
  名称：

  A NEW METHOD FOR THE SYNTHESIS OFN²-ALKYLGUANOSINES USING MITSUNOBU REACTION AS A KEY STEP

  摘要：

  Peracetylated guanosine was reacted With POCl3 to give an 2-acetamido-6-chloro-9H-purine derivative, which was condensed with primary or secondary alcohols to give N-2-alkylated analogues. The products were treated with mercaptoethanol in the presence of sodium methoxide to afford N-2-alkylguanosines.

  DOI：

  10.1081/ncn-100105245

文献信息

• Nucleosides and nucleotides. 103. 2-Alkynyladenosines: a novel class of selective adenosine A2 receptor agonists with potent antihypertensive effects
  作者：Akira Matsuda、Misao Shinozaki、Toyofumi Yamaguchi、Hiroshi Homma、Rie Nomoto、Tadashi Miyasaka、Yohko Watanabe、Toichi Abiru

  DOI：10.1021/jm00080a007

  日期：1992.1

  Additionally, we describe how hypotensive activity and heart rate decrease brought on by 5 and some other compounds with spontaneously hypertensive rats are proportional to the order of the potency to both A1 and A2 binding affinities. Thus, 2-alkynyladenosines are interesting and promising as antihypertensive agents that should be considered for further detailed preclinical evaluation.

  描述了一系列2-炔基腺苷在A1和A2腺苷受体上的合成和受体结合活性。在含三乙胺的N，N-二甲基甲酰胺中，在双（三苯基膦）二氯化钯和碘化亚铜的存在下，钯催化的2-碘腺苷（4a）与各种末端炔的交叉偶联反应生成2-炔基腺苷（5a-r）。一种经济的合成方法，用于制备9a（2,3,5-三-O-乙酰基-1-β-D-呋喃呋喃糖基）-6-氯-2-碘代嘌呤++ +（2），这是4a的前体，也包括在内。2-（1-辛炔-1-基）腺苷（5e）和2-（1-乙炔-1-基）腺苷（9）的几种转化反应以及6-氯嘌呤衍生物11和8的相似交叉偶联反应还报道了带有1-辛炔的-溴腺苷（13）。在大鼠脑中针对A1和A2腺苷受体结合活性进行测试的许多这类2-炔基腺苷对A2腺苷受体具有选择性。其中，2-（1-己炔-1-基）腺苷（5c）对A1和A2受体的亲和力最高，Ki值分别为126.5和2.8 nM。讨论了这一系列化合物的结构活性关系，包
• SYNTHESIS OF<i>N</i>²-ALKYLGUANOSINE USING MITSUNOBU REACTION AS A KEY STEP
  作者：Tokumi Maruyama、Aya Yorikane、Shigetada Kozai

  DOI：10.1081/ncn-100002462

  日期：2001.3.31

  Peracetylated guanosine was reacted with POCl3 to give an 2-acetamido-6-chloro-9H-purine derivative, which was condensed with primary or secondary alcohols to give N-2-alkylated analogues. The products were treated with mercaptoethanol in the presence of sodium methoxide to afford N-2-alkylguanosines.
• Synthesis of 3-(2-deoxy-β-d-ribofuranosyl)pyridin-2-one and 2-amino-6-(N,N-dimethylamino)-9-(2-deoxy-β-d-ribofuranosyl)purine derivatives for an unnatural base pair
  作者：Masahide Ishikawa、Ichiro Hirao、Shigeyuki Yokoyama

  DOI：10.1016/s0040-4039(00)00520-7

  日期：2000.5

  An unnatural base pair, 2-amino-6-(N,N-dimethylamino)purine (denoted x) and pyridin-2-one (denoted y), was designed to prove the structural requirements for base pair formation involving shape complementarity. It was expected that y might satisfy the structural requirements for pairing with x, in which the bulky 6-dimethylamino group may eliminate base pairing with the natural bases. As chemical or biological substrates for DNA synthesis, the phosphoramidite of x and the 2'-deoxy-C3-ribonucleoside triphosphate of y (dyTP) were synthesized, and the incorporation experiment was demonstrated by using the Klenow fragment of Escherichia call DNA polymerase I. (C) 2000 Elsevier Science Ltd. All rights reserved.