N²,N²-diethyl-2'-deoxyguanosine | 236389-19-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N²,N²-diethyl-2'-deoxyguanosine
• 英文别名: N2,N2-diethyl-2'-deoxyguanosine；2-(diethylamino)-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 236389-19-8
• 化学式: C₁₄H₂₁N₅O₄
• 分子量: 323.352
• InChiKey: JLKDOZVYGPEKBD-IVZWLZJFSA-N

物化性质

• 密度：
  1.57±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜；甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

制备方法与用途

2'-脱氧-N₂,N₂二乙基鸟苷是一种嘌呤核苷类似物，具有广泛抗肿瘤活性，尤其针对惰性淋巴系统恶性肿瘤。其抗癌机制主要通过抑制DNA合成和诱导细胞凋亡来实现。

反应信息

• 作为反应物：
  描述：

  N²,N²-diethyl-2'-deoxyguanosine 在 水 、 一氧化二氮 作用下， 生成
  参考文献：
  名称：

  New Insights into the Reaction Paths of Hydroxyl Radicals with 2′-Deoxyguanosine

  摘要：

  The reaction of HO(center dot) radical with 2'-deoxyguanosine is intensively studied as a model for DNA damage. Several aspects related to the reaction paths responsible for the most relevant lesions are not well understood. We have reinvestigated the reaction of HO(center dot) with 2'-deoxyguanosine by pulse radiolysis and extended our studies to a variety of substituted derivatives. The main path of hydrogen abstraction was confirmed to be from the exocyclic NH(2) group, followed by a water-assisted tautomerization. The rate constant (k = 2.3 x 10(4) s(-1)) obtained from the spectral changes at 620 rim is influenced by the substituent at the C8 position. When N1-H is replaced by N1-CH(3), the tautomerization does not occur. The spectral changes at 370 nm that correspond to a rate constant of 6.9 x 10(5) s(-1) were assigned to the cyclization of 2'-deoxyguanosin-5'-yl radical with formation of 5',8-cyclo-2'-deoxyguanosine as the product. When NEt(2) replaces the exocyclic NH(2), the spectral changes at all wavelengths follow second-order kinetics, suggesting a "slow" ring-opening of the 8-hydroxyl adduct of 2'-deoxyguanosine.

  DOI：

  10.1021/tx2003245
• 作为产物：
  描述：

  2'-脱氧鸟苷 、 乙醛 在 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以80%的产率得到N²-ethyl-2'-deoxyguanosine
  参考文献：
  名称：

  一种方便的方法来制备N（2）-乙基鸟嘌呤核苷和核苷酸。

  摘要：

  DOI：

  10.1021/jo990500e

文献信息

• A Convenient Method for the Preparation of <i>N</i>²-Ethylguanine Nucleosides and Nucleotides
  作者：Magoichi Sako、Hiroyoshi Kawada、Kosaku Hirota

  DOI：10.1021/jo990500e

  日期：1999.7.1
• New Insights into the Reaction Paths of Hydroxyl Radicals with 2′-Deoxyguanosine
  作者：Chryssostomos Chatgilialoglu、Mila D’Angelantonio、Gabriel Kciuk、Krzysztof Bobrowski

  DOI：10.1021/tx2003245

  日期：2011.12.19

  The reaction of HO(center dot) radical with 2'-deoxyguanosine is intensively studied as a model for DNA damage. Several aspects related to the reaction paths responsible for the most relevant lesions are not well understood. We have reinvestigated the reaction of HO(center dot) with 2'-deoxyguanosine by pulse radiolysis and extended our studies to a variety of substituted derivatives. The main path of hydrogen abstraction was confirmed to be from the exocyclic NH(2) group, followed by a water-assisted tautomerization. The rate constant (k = 2.3 x 10(4) s(-1)) obtained from the spectral changes at 620 rim is influenced by the substituent at the C8 position. When N1-H is replaced by N1-CH(3), the tautomerization does not occur. The spectral changes at 370 nm that correspond to a rate constant of 6.9 x 10(5) s(-1) were assigned to the cyclization of 2'-deoxyguanosin-5'-yl radical with formation of 5',8-cyclo-2'-deoxyguanosine as the product. When NEt(2) replaces the exocyclic NH(2), the spectral changes at all wavelengths follow second-order kinetics, suggesting a "slow" ring-opening of the 8-hydroxyl adduct of 2'-deoxyguanosine.