2-氨基-6H-嘌呤-6-酮3-氧化物 | 18905-29-8

• 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: 2-氨基-6H-嘌呤-6-酮3-氧化物
• 英文名称: Guanine 3-N-oxide
• 英文别名: 3-oxoguanine
• CAS: 18905-29-8；68375-46-2
• 化学式: C₅H₅N₅O₂
• 分子量: 167.127
• InChiKey: NHFYUOGLANHPMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  295.68°C (rough estimate)
• 密度：
  1.5442 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.53
• 重原子数：
  12.0
• 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：
  114.5
• 氢给体数：
  3.0
• 氢受体数：
  4.0

安全信息

• 海关编码：
  2933990090

文献信息

• Synthesis and Base-Pairing of Self-Complementary Mesomeric Betaines of Guanine
  作者：Andreas Schmidt、Nikoloz Kobakhidze

  DOI：10.1246/cl.2002.222

  日期：2002.2

  Substitution of 8-H of guanine-N-oxide was accomplished by pyridine, 4-dimethylaminopyridine and acetyl chloride, respectively, to give a cationic purine base after hydrolysis. Deprotonation formed mesomeric betaines of guanine. ESI mass spectrometry and 1H NMR revealed their self-complementarity. Base-pairing to cytosine was observed with a fully protected DNA model compound.

  分别用吡啶、4-二甲氨基吡啶和乙酰氯取代鸟嘌呤-N-氧化物的8-H，水解后得到阳离子嘌呤碱。去质子化形成鸟嘌呤的中间体甜菜碱。ESI 质谱和 1 H NMR 揭示了它们的自互补性。使用完全保护的 DNA 模型化合物观察到与胞嘧啶的碱基配对。
• Synthesis of 2-amino-6-chloro- and 2,6-diammopunne 3-oxides
  作者：Israel Scheinfeld、James C. Parham、George Bosworth Brown

  DOI：10.1002/jhet.5570190551

  日期：1982.9

  N-Oxidation of 2-amino-6-chloropurine to the 3-oxide provided a convenient intermediate for the synthesis of 2-amino-6-substituted purine 3-oxides, including the previously unavailable 2,6-diaminopurine 3-oxide. Thiation of the 6-halogen was accompanied by reduction of the N-oxide. The properties of the 1- and 3-oxides of 2,6-diaminopurine are compared.

  Ñ 2-氨基-6-氯嘌呤与3-氧化物的氧化作用为2-氨基-6-取代的嘌呤-3-氧化物，包括先前不可用的2,6-二氨基-3-氧化物的合成中提供了一个方便的中间体。6-卤素的硫原子伴随着N-氧化物的还原。比较了2，6-二氨基嘌呤的1-和3-氧化物的性质。
• Deoxyribonucleic acid modification by mutagenic 3-amino-1-methyl-5H-pyrido(4,3-b)indole: The chemical events.
  作者：YUICHI HASHIMOTO、KOICHI SHUDO、TOSHIHIKO OKAMOTO

  DOI：10.1248/cpb.32.4300

  日期：——

  3-Amino-1-methyl-5H-pyrido [4, 3-b] indole (Trp-P-2) is a mutagen/carcinogen isolated from a pyrolysate of L-tryptophan. The active metabolite of Trp-P-2, 3-hydroxyamino-1-methyl-5H-pyrido [4, 3-b] indole (N-OH-Trp-P-2), was synthesized and the chemical reactions of N-OH-Trp-P-2 with deoxyribonucleic acid were investigated. The structure of the nucleic acid base covalently bound with Trp-P-2 was elucidated as 3-(C8-guanyl) amino-1-methyl-5H-pyrido [4, 3-b] indole (Gua-Trp-P-2) by comparison with a synthetic sample. The initial chemical events in carcinogenesis caused by Trp-P-2 were established.

  3-氨基-1-甲基-5H-吡啶并[4，3-b]吲哚（Trp-P-2）是从 L-色氨酸的热解产物中分离出来的一种诱变剂/致癌物质。研究人员合成了 Trp-P-2 的活性代谢物--3-羟基氨基-1-甲基-5H-吡啶并[4，3-b]吲哚（N-OH-Trp-P-2），并研究了 N-OH-Trp-P-2 与脱氧核糖核酸的化学反应。通过与合成样品的对比，阐明了与 Trp-P-2 共价结合的核酸碱基的结构为 3-(C8-鸟嘌呤基)氨基-1-甲基-5H-吡啶并[4, 3-b] 吲哚（Gua-Trp-P-2）。确定了 Trp-P-2 致癌的最初化学事件。
• Synthesis, Tautomerism and Calculations of Mesomeric Betaines of Guanine
  作者：Andreas Schmidt、Nikoloz Kobakhidze

  DOI：10.3987/com-02-9634

  日期：——

  Reaction of purine-N-oxide (4) with 4-(dimethylamino)pyridine and acetyl chloride, followed by the treatment with hydrochloric acid gave the purine-pyridinium salt (6) which was deprotonated to the mesomeric betaine (7). Depending on the reaction conditions, 4-methylpyridine and pyridine, respectively, converted the nucleoside (8) into the pyridinium salts (9) and (10), or into the mesomeric betaines (11) and (12). According to calculations, the conjugated tautomers (A-D) of betaine (7) are more stable than the cross-conjugated tautomer (7E).
• SCHEINFELD, I.;PARHAM, J. C.;BROWN, G. B., J. HETEROCYCL. CHEM., 1982, 19, N 5, 1231-1233
  作者：SCHEINFELD, I.、PARHAM, J. C.、BROWN, G. B.

  DOI：——

  日期：——