5H-咪唑并[5,4-e]三嗪-4-胺 | 2308-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 中文名称: 5H-咪唑并[5,4-e]三嗪-4-胺
• 英文名称: 2-azaadenine
• 英文别名: 5(7)H-imidazo[4,5-d][1,2,3]triazin-4-ylamine；6-amino-2-azapurine；4-Amino-imidazo<4,5-d>-1,2,3-triazin；2-Aza-adenin；5H-imidazo[4,5-d]triazin-4-amine
• CAS: 2308-56-7
• 化学式: C₄H₄N₆
• mdl: MFCD20617180
• 分子量: 136.116
• InChiKey: QHVZREGCOXMZPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5H-咪唑并[5,4-e]三嗪-4-胺 在 xanthine oxide ase 作用下， 生成 4-amino-5,7-dihydro-imidazo[4,5-d][1,2,3]triazin-6-one
  参考文献：
  名称：

  Shaw; Woolley, Journal of Biological Chemistry, 1952, vol. 194, p. 641,651

  摘要：

  DOI：
• 作为产物：
  描述：

  Imidazo<4,5-d>-1,2,3-triazin-4-thion 生成 5H-咪唑并[5,4-e]三嗪-4-胺
  参考文献：
  名称：

  POSPELOVA, T. A.;SELEZNEVA, I. S.;USOVA, V. K.;MOKRUSHIN, V. S., KOMPONENTY NUKLEIN. KISLOT: 8 BCEC. SIMP. PO TSELENAPRAVL. IZYSKANIYU LEK+

  摘要：

  DOI：

文献信息

• Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells
  作者：Ivan Votruba、Antonín Holý、Hana Dvořáková、Jaroslav Günter、Dana Hocková、Hubert Hřebabecký、Tomas Cihlar、Milena Masojídková

  DOI：10.1135/cccc19942303

  日期：——

  Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs. All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N⁹-isomers in the purine and N¹-isomers in the pyrimidine series. Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety. The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N⁷-nitrogen atom. On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives. Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding N-dimethylaminomethylene derivative which is then ammonolyzed. The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-dideoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-dideoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.

  藻酸盐凝胶包埋的辅助胸腺嘧啶依赖菌株大肠杆菌细胞催化2'-脱氧尿嘧啶的2-脱氧-D-核糖呋喃基团转移到嘌呤和嘧啶碱基以及它们的氮杂和去氮类似物。所有实验都不可避免地产生β-异构体；在大多数情况下，反应是区域特异性的，产生嘌呤中的N⁹-异构体和嘧啶系列中的N¹-异构体。此外，2,3-二脱氧核苷酸可以作为糖基团的供体。嘌呤碱基的受体活性仅在取代上有少许影响，唯一的条件是存在N⁷-氮原子。另一方面，在嘧啶系列中，活性仅限于大多数短链5-烷基和5-卤代尿嘧啶衍生物的狭窄选择。含氨基的杂环碱基会发生脱氨作用；可以通过将碱基转化为相应的N-二甲氨基甲烯基衍生物来避免这种情况，然后进行氨解作用。该方法通过分离腺嘌呤、鸟嘌呤、2-氯腺嘌呤、6-甲基嘌呤、8-氮杂腺嘌呤、8-氮杂鸟嘌呤、1-去氮腺嘌呤、3-去氮腺嘌呤的9-(2-脱氧-β-D-核糖呋喃基)衍生物，5-乙基尿嘧啶、5-氟尿嘧啶的1-(2-脱氧-β-D-核糖呋喃基)衍生物，以及9-(2,3-二脱氧-β-D-戊呋喃基)缺氧嘌呤、9-(2,3-二脱氧-β-D-戊呋喃基)-6-甲基嘌呤和其他核苷酸的验证。
• Acyclic Nucleoside and Nucleotide Analogs Derived from 2-Azaadenine
  作者：Dana Hocková、Milena Masojídková、Miloš Buděšínský、Antonín Holý

  DOI：10.1135/cccc19950224

  日期：——

  Alkylation of cesium salt of 2-azaadenine with appropriate synthons afforded the following acyclic analogs of nucleosides and nucleotides: (S)-9-(2,3-dihydroxypropyl)-2-azaadenine (VI), 3-(2-azaadenin-9-yl)-2-hydroxypropanoic acid (VIII), 9-(2-phosphonomethoxyethyl)-2-azaadenine (Xb), (R)-9-(2-phosphonomethoxypropyl)-2-azaadenine (XIb) and (S)-9-(3-hydroxy-2-phosphonomethoxypropyl)-2-azaadenine (XVIb). In some cases the N-2 isomers were also isolated.

  用适当的合成物与2-azaadenine的铯盐进行烷基化，得到了以下的无环类似物：(S)-9-(2,3-二羟基丙基)-2-azaadenine (VI), 3-(2-azaadenin-9-yl)-2-羟基丙酸 (VIII), 9-(2-磷酸甲氧基乙基)-2-azaadenine (Xb), (R)-9-(2-磷酸甲氧基丙基)-2-azaadenine (XIb) 和 (S)-9-(3-羟基-2-磷酸甲氧基丙基)-2-azaadenine (XVIb)。在某些情况下，也分离出了N-2异构体。
• Woolley; Shaw, Journal of Biological Chemistry, 1951, vol. 189, p. 401,402
  作者：Woolley、Shaw

  DOI：——

  日期：——
• POSPELOVA, T. A.;SELEZNEVA, I. S.;USOVA, V. K.;MOKRUSHIN, V. S., KOMPONENTY NUKLEIN. KISLOT: 8 BCEC. SIMP. PO TSELENAPRAVL. IZYSKANIYU LEK+
  作者：POSPELOVA, T. A.、SELEZNEVA, I. S.、USOVA, V. K.、MOKRUSHIN, V. S.

  DOI：——

  日期：——
• PUSHKAREVA Z. V.; OFITSEROV V. I.; MOKRUSHIN V. S.; AGLITSKAYA K. V., XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1975, HO 8, 1141-1145
  作者：PUSHKAREVA Z. V.、 OFITSEROV V. I.、 MOKRUSHIN V. S.、 AGLITSKAYA K. V.

  DOI：——

  日期：——