3-羟基-3,7-二氢-6H-嘌呤-6-酮 | 19765-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 3-羟基-3,7-二氢-6H-嘌呤-6-酮
• 英文名称: hypoxanthine-3-N-oxide
• 英文别名: H3NO；3-oxy-1,7(9)-dihydro-purin-6-one；Hypoxanthin 1-N-oxid；Hypoxanthin-3-N-oxid
• CAS: 19765-65-2
• 化学式: C₅H₄N₄O₂
• mdl: MFCD12912670
• 分子量: 152.112
• InChiKey: CPIUTOFQEKHTNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.34
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.74
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  6-methoxypurine-3-N-oxide 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以76%的产率得到3-羟基-3,7-二氢-6H-嘌呤-6-酮
  参考文献：
  名称：

  摘要：

  In laboratory and field-trapping studies, we exposed fathead minnows (Pimephales promelas) and finescale dace (Chrosomus neogaeus) to hypoxanthine-3-N-oxide and a suite of structurally and functionally similar compounds in order to determine if: (1) hypoxanthine-3-N-oxide functions as a chemical alarm signal in ostariophysan fishes and (2) the purine skeleton, a structural component, or the nitrogen oxide, a functional component, or both act as the molecular trigger in this chemical alarm signaling system. Minnows and dace exhibited significant antipredator responses when exposed to conspecific skin extract or hypoxanthine-3-N-oxide (increased shoaling and decreased area use) and the functionally similar pyridine-N-oxide (increased shoaling) but not to structurally similar molecules lacking a nitrogen oxide functional group or to a swordtail skin extract control. Field-trapping studies revealed similar results. Traps labeled with fathead minnows skin extract, hypoxanthine-3-N-oxide, or pyridine-N-oxide caught significantly fewer fish than did those labeled with distilled water. These data strongly suggest that the nitrogen oxide functional group acts as the chief molecular trigger in the Ostariophysan alarm pheromone system and that, contrary to previous research, hypoxanthine-3-N-oxide may be one of several possible molecules that function as a chemical alarm signal. Here we report the first example of a single functional group capable of eliciting a suite of behavioral responses.

  DOI：

  10.1023/a:1005445629144

文献信息

• ——
  作者：Grant E. Brown、James C. Adrian, Jr.、Erin Smyth、Heather Leet、Scott Brennan

  DOI：10.1023/a:1005445629144

  日期：——

  In laboratory and field-trapping studies, we exposed fathead minnows (Pimephales promelas) and finescale dace (Chrosomus neogaeus) to hypoxanthine-3-N-oxide and a suite of structurally and functionally similar compounds in order to determine if: (1) hypoxanthine-3-N-oxide functions as a chemical alarm signal in ostariophysan fishes and (2) the purine skeleton, a structural component, or the nitrogen oxide, a functional component, or both act as the molecular trigger in this chemical alarm signaling system. Minnows and dace exhibited significant antipredator responses when exposed to conspecific skin extract or hypoxanthine-3-N-oxide (increased shoaling and decreased area use) and the functionally similar pyridine-N-oxide (increased shoaling) but not to structurally similar molecules lacking a nitrogen oxide functional group or to a swordtail skin extract control. Field-trapping studies revealed similar results. Traps labeled with fathead minnows skin extract, hypoxanthine-3-N-oxide, or pyridine-N-oxide caught significantly fewer fish than did those labeled with distilled water. These data strongly suggest that the nitrogen oxide functional group acts as the chief molecular trigger in the Ostariophysan alarm pheromone system and that, contrary to previous research, hypoxanthine-3-N-oxide may be one of several possible molecules that function as a chemical alarm signal. Here we report the first example of a single functional group capable of eliciting a suite of behavioral responses.