6-氯-9-(2,3,5-三-O-乙酰基呋喃戊糖基)-1,9-二氢-2H-嘌呤-2-酮 | 161923-50-8

• 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: 6-氯-9-(2,3,5-三-O-乙酰基呋喃戊糖基)-1,9-二氢-2H-嘌呤-2-酮
• 中文别名: aD-laminarabioside七乙酸甲酯
• 英文名称: 6-chloro-2-hydroxy-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) purine
• 英文别名: 6-chloro-2-hydroxy-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine；2',3',5'-triacetyl-6-chloroguanosine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-chloro-2-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 161923-50-8
• 化学式: C₁₆H₁₇ClN₄O₈
• 分子量: 428.786
• InChiKey: UDPLUTIBYLKPII-SDBHATRESA-N

物化性质

• 溶解度：
  可溶于二氯甲烷、乙醚、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-氯-9-(2,3,5-三-O-乙酰基呋喃戊糖基)-1,9-二氢-2H-嘌呤-2-酮 在 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 7.0h， 生成 巴豆苷
  参考文献：
  名称：

  Napoli, Lorenzo De; Montesarchio, Daniela; Piccialli, Gennaro, Journal of the Chemical Society. Perkin transactions I, 1995, # 1, p. 15 - 18

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二氢-9-(2’,3’,5’-三-O-乙酰基-beta-D-呋喃核糖基)嘌呤 在 四氯化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以84%的产率得到6-氯-9-(2,3,5-三-O-乙酰基呋喃戊糖基)-1,9-二氢-2H-嘌呤-2-酮
  参考文献：
  名称：

  Napoli, Lorenzo De; Montesarchio, Daniela; Piccialli, Gennaro, Journal of the Chemical Society. Perkin transactions I, 1995, # 1, p. 15 - 18

  摘要：

  DOI：

文献信息

• Synthesis of 2-aralkoxyadenosines and 2-alkoxyadenosines
  申请人：——

  公开号：US20030199686A1

  公开（公告）日：2003-10-23

  The invention provides new methods for synthesis of 2-aralkyloxyadenosines and 2-alkoxyadenosines. The invention is particularly useful for synthesis of 2-[2-(4-chlorophenyl)ethoxy]adenosine. Preferred methods of the invention include activating a guanosine compound followed by hydrolysis; alkylating the hydrolyzed compound with subsequent animation to provide a 2-aralkyloxyadenosine or a 2-alkoxyadenosine compound.

  这项发明提供了合成2-芳基氧基腺苷和2-烷氧基腺苷的新方法。该发明特别适用于合成2-[2-(4-氯苯基)乙氧基]腺苷。该发明的首选方法包括激活鸟苷化合物，然后进行水解；烷基化水解后的化合物，随后进行胺化，以提供2-芳基氧基腺苷或2-烷氧基腺苷化合物。
• Structure−Activity Relationships of 2,<i>N</i>⁶,5‘-Substituted Adenosine Derivatives with Potent Activity at the A_2B Adenosine Receptor
  作者：Hayamitsu Adachi、Krishnan K. Palaniappan、Andrei A. Ivanov、Nathaniel Bergman、Zhan-Guo Gao、Kenneth A. Jacobson

  DOI：10.1021/jm061278q

  日期：2007.4.1

  2, N-6, and 5'-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A(2B)AR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N-6-ethyl or N-6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-( 3-( indolyl)ethyloxy) adenosine series. Indole 5 ''- or 6 ''-halo substitution was favored at the A(2B)AR, but a 5'-N-ethylcarboxyamide did not further enhance potency. 2-(3 ''-(6 ''-Bromoindolyl)ethyloxy)adenosine 28 displayed an A(2B)AR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5'-N-ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A(2B) and A(2A)ARs and a low efficacy partial agonist at A(1) and A(3)ARs. Thus, we have identified and optimized 2-(2-arylethyl) oxo moieties in AR agonists that enhance A(2B)AR potency and selectivity.
• [EN] A2 ADENOSINE RECEPTOR AGONISTS<br/>[FR] AGONISTES DES RÉCEPTEURS D'ADÉNOSINE A2
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2009006089A3

  公开（公告）日：2009-04-09
• 6-Chloroxanthosine, a Useful Intermediate for the Efficient Syntheses of [6-¹⁵N]-Isoguanosine, Isoinosine and Other Purine Nucleoside Analogues
  作者：L. De Napoli、A. Messere、D. Montesarchio、G. Piccialli、M. Varra

  DOI：10.1080/07328319708002532

  日期：1997.1

  6-Chloroxanthosine 1, when activated towards nucleophilic displacement at the 6-C position by conversion into the corresponding 3-N-(2,4-dinitrophenyl) derivative 4, reacted with aq. (NH3)-N-15 to afford [6-N-15]-isoguanosine 3b in 81% overall yield. Catalytic hydrogenation (Pd/C) of 1 led in 60% yield to isoinosine 8; alternatively, this could be obtained in 88% overall yield through alkaline hydrolysis of triphenylphosphonium salt 6, synthesized from 1 by reaction with PPh(3). The reactivity of 1 was further explored by treating it with primary and secondary amines: the 6-N propylamino and the 6-N piperidinyl derivatives (5a and 5b, respectively) could thus both be prepared in more than 90% yield.
• SYNTHESIS OF 2-ARALKOXY ADENOSINES AND 2-ALKOXYADENOSINES
  申请人：King Pharmaceuticals Research and Development Inc.

  公开号：EP1446413A1

  公开（公告）日：2004-08-18