9-bromo-3-(β-D-ribofuranosyl)pyrazolo<3,2-i>purine | 146462-37-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-bromo-3-(β-D-ribofuranosyl)pyrazolo<3,2-i>purine
• 英文别名: (2R,3R,4S,5R)-2-(9-bromopyrazolo[5,1-f]purin-3-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 146462-37-5
• 化学式: C₁₂H₁₂BrN₅O₄
• 分子量: 370.162
• InChiKey: MOAAHIWXADZJIO-XYHAGOFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-bromo-3-(β-D-ribofuranosyl)pyrazolo<3,2-i>purine 在 吡啶 、 氨 、 乙酸酐 、 copper(II) nitrate 作用下， 反应 3.0h， 生成 (2R,3S,4R,5R)-2-Hydroxymethyl-5-(9-nitro-pyrazolo[5,1-i]purin-3-yl)-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  新的荧光核苷，3-β-D-呋喃核糖基吡唑啉（3,2-i）嘌呤衍生物的合成及其细胞毒活性。

  摘要：

  新型核苷3-β-D-呋喃核糖基吡唑并（3,2-i）嘌呤（8）及其9-取代的溴，硝基和氨基化合物（3、6和11）是由完全保护的3-β- D-核呋喃糖基（3,2-i）嘌呤-9-羧酰胺1，通过溴代酰胺化（ipso溴化）。化合物3、8和11对培养的小鼠白血病L5178Y细胞显示抗白血病活性，而9-取代的硝基，酯和酰胺化合物（6、12和13）没有细胞毒性。

  DOI：

  10.1248/cpb.40.2585
• 作为产物：
  描述：

  6-chloro-9-<2,3-O-isopropylidene-5-O-(2-tetra-hydropyranyl)-β-D-ribofuranosyl>purine 在 palladium on activated charcoal potassium phosphate buffer 、 氨 、 水 、 氢气 、 溴 、 sodium hydride 、 碳酸氢钠 、 一水合肼 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 100.0 ℃ 、405.3 kPa 条件下， 反应 147.92h， 生成 9-bromo-3-(β-D-ribofuranosyl)pyrazolo<3,2-i>purine
  参考文献：
  名称：

  Design and Synthesis of a New Fluorescent Tricyclic Nucleoside, 3-.beta.-D-Ribofuranosylpyrazolo[3,2-i]purine

  摘要：

  The novel nucleoside, 3-beta-D-ribofuranosylpyrazolo[3,2-i]purine, has been prepared in seven steps from a fully protected 6-chloropurine derivative including a one-step reaction for the preparation of an ethyl 3-beta-D-ribofuranosylpyrazolo[3,2-i]purine derivative from 6-enamino purine and hydrazine. The mechanism for the preparation of 9-ethyl-substituted pyrazolo[3,2-i]purines was elucidated. First, the hydrazino moiety of 6-enamino purine attacks at the C-6 carbon of the purine ring to give a spiro intermediate; this is followed by ring opening and cyclization. The new tricyclic nucleoside exhibited stronger fluorescence than that of 1,N6-ethenoadenosine. Also, the compound and the 9-bromo-substituted pyrazolo[3,2-i]purine nucleoside showed cytotoxic activities against human leukemia CCRF-HSB-2 cells in culture.

  DOI：

  10.1021/jo00085a046

文献信息

• Synthesis of 3-(β-D-ribofuranosyl)pyrazolo[3,2-<i>i</i>]-purine derivatives and their cytotoxic activities
  作者：Norimitsu Hamamichi、Tadashi Miyasaka

  DOI：10.1002/jhet.5570300203

  日期：1993.3

  9-Amino-3-(β-D-ribofuranosyl)pyrazolo[3,2-i|purine (6) has been prepared from a fully protected 3-(β-D-ribofuranosyl)pyrazolo[3,2-i]purine (2) and the 9-bromo substituted derivative 3 by nitration, followed by reduction. Reaction of 9-bromo-3-(β-D-ribofuranosyl)pyrazolo[3,2-i)purine (1b) with alkali gave the (pyrazol-3-yl)imidazole derivative, followed by diazocyclization with sodium nitrate to give

  9-氨基-3-（β-d-D-呋喃核糖基）吡唑并[3,2-我|嘌呤（6）已经从完全保护的制备3-（β-d-D-呋喃核糖基）吡唑并[3,2-我〕嘌呤（2）和9-溴取代的衍生物3通过硝化，然后还原。9-溴-3-（β-D-呋喃呋喃糖基）吡唑并[3,2- i ]嘌呤（1b）与碱反应，得到（吡唑-3-基）咪唑衍生物，然后用硝酸钠重氮环化得到9脱乙酰基后生成-溴-3-（β-D-呋喃核糖基）咪唑并[ 4,5- d ]吡唑并[2,3- c ] [1,2,3]三嗪（10）。化合物6和10 对白血病细胞表现出细胞毒活性。
• Design and Synthesis of a New Fluorescent Tricyclic Nucleoside, 3-.beta.-D-Ribofuranosylpyrazolo[3,2-i]purine
  作者：Norimitsu Hamamichi、Tadashi Miyasaka

  DOI：10.1021/jo00085a046

  日期：1994.3

  The novel nucleoside, 3-beta-D-ribofuranosylpyrazolo[3,2-i]purine, has been prepared in seven steps from a fully protected 6-chloropurine derivative including a one-step reaction for the preparation of an ethyl 3-beta-D-ribofuranosylpyrazolo[3,2-i]purine derivative from 6-enamino purine and hydrazine. The mechanism for the preparation of 9-ethyl-substituted pyrazolo[3,2-i]purines was elucidated. First, the hydrazino moiety of 6-enamino purine attacks at the C-6 carbon of the purine ring to give a spiro intermediate; this is followed by ring opening and cyclization. The new tricyclic nucleoside exhibited stronger fluorescence than that of 1,N6-ethenoadenosine. Also, the compound and the 9-bromo-substituted pyrazolo[3,2-i]purine nucleoside showed cytotoxic activities against human leukemia CCRF-HSB-2 cells in culture.
• Synthesis of new fluorescent nucleosides, 3-.BETA.-D-ribofuranosylpyrazolo(3,2-i)purine derivatives and their cytotoxic activities.
  作者：Norimitsu HAMAMICHI、Tadashi MIYASAKA

  DOI：10.1248/cpb.40.2585

  日期：——

  The novel nucleosides 3-beta-D-ribofuranosylpyrazolo(3,2-i) purine (8) and their 9-substituted bromo, nitro and amino compounds (3, 6 and 11) have been prepared from a fully protected 3-beta-D-ribofuranosyl(3,2-i)purine-9-carboxyamide 1 by bromodeamidation (ipso bromination). Compounds 3, 8 and 11 exhibited antileukemic activity against mouse leukemia L5178Y cells in culture, while the 9-substituted

  新型核苷3-β-D-呋喃核糖基吡唑并（3,2-i）嘌呤（8）及其9-取代的溴，硝基和氨基化合物（3、6和11）是由完全保护的3-β- D-核呋喃糖基（3,2-i）嘌呤-9-羧酰胺1，通过溴代酰胺化（ipso溴化）。化合物3、8和11对培养的小鼠白血病L5178Y细胞显示抗白血病活性，而9-取代的硝基，酯和酰胺化合物（6、12和13）没有细胞毒性。