4-amino-1-[2'-deoxy-β-D-erythro-pentofuranosyl]-7-nitro-1H-imidazo[4,5-c]pyridine | 750632-67-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 4-amino-1-[2'-deoxy-β-D-erythro-pentofuranosyl]-7-nitro-1H-imidazo[4,5-c]pyridine
• 英文别名: (2R,3S,5R)-5-(4-amino-7-nitroimidazo[4,5-c]pyridin-1-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 750632-67-8
• 化学式: C₁₁H₁₃N₅O₅
• 分子量: 295.255
• InChiKey: BNEYIHUXKZKRAV-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-amino-1-[2'-deoxy-β-D-erythro-pentofuranosyl]-7-nitro-1H-imidazo[4,5-c]pyridine 在 吡啶 、 咪唑 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 4-isobutyrylamino-1-[2'-deoxy-β-D-erythro-pentofuranosyl]-7-nitro-1H-imidazo[4,5-c]pyridine
  参考文献：
  名称：

  Synthesis of 3-deaza-3-nitro-2′-deoxyadenosine

  摘要：

  Photoactivable deoxyadenosine mimic, 3-deaza-3-nitro-2'-deoxyadetiosine (2), was prepared using two different synthetic routes. The first route involved base catalyzed glycosylation of 3-deaza-3-nitroadenine, which was prepared by regioselective nitration of 3-deazaadenine. In the second route, the convertible nucleoside 6-O-(2,4,6-trimethylphenyl)-3-deaza-2'-deoxyadenosine (28) was used to introduce 6-NH2 group in the last step. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.040
• 作为产物：
  描述：

  4-hydrazino-1H-imidazo[4,5-c]pyridine 在 吡啶 、 氢氧化钾 、 tris[2-(2-methoxyethyl)ethyl]amine 、 硫酸 、 氨 、 氢气 、 硝酸 、 镍 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 7.58h， 生成 4-amino-1-[2'-deoxy-β-D-erythro-pentofuranosyl]-7-nitro-1H-imidazo[4,5-c]pyridine
  参考文献：
  名称：

  Synthesis of 3-deaza-3-nitro-2′-deoxyadenosine

  摘要：

  Photoactivable deoxyadenosine mimic, 3-deaza-3-nitro-2'-deoxyadetiosine (2), was prepared using two different synthetic routes. The first route involved base catalyzed glycosylation of 3-deaza-3-nitroadenine, which was prepared by regioselective nitration of 3-deazaadenine. In the second route, the convertible nucleoside 6-O-(2,4,6-trimethylphenyl)-3-deaza-2'-deoxyadenosine (28) was used to introduce 6-NH2 group in the last step. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.040

文献信息

• 3-Nitro-3-deaza-2‘-deoxyadenosine as a Versatile Photocleavable 2‘-Deoxyadenosine Mimic
  作者：Caroline Crey-Desbiolles、Jean Lhomme、Pascal Dumy、Mitsuharu Kotera

  DOI：10.1021/ja047976m

  日期：2004.8.1

  A new photocleavable 2'-deoxyadenosine mimic, 3-nitro-3-deaza-2'-deoxyadenosine (NidA), was prepared and introduced into DNA fragments via its 6-O-trimethylphenyl precursor phophoramidite. Photocleavage of the resulting oligonucleotide is highly efficient in single and double strands. Hybridization properties of NidA are very similar to those of deoxyadenosine.