2(1H)-嘧啶酮,5,6-二氨基- | 23899-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2(1H)-嘧啶酮,5,6-二氨基-
• 英文名称: 5-aminocytosine
• 英文别名: 4,5-diaminopyrimidin-2(1H)-one；5-Amino-cytosin；4,5-Diaminopyrimidin-2-ol；5,6-diamino-1H-pyrimidin-2-one
• CAS: 23899-73-2
• 化学式: C₄H₆N₄O
• mdl: MFCD19203456
• 分子量: 126.118
• InChiKey: ZOAGFDYQEMSRDR-UHFFFAOYSA-N

物化性质

• 密度：
  1.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  2(1H)-嘧啶酮,5,6-二氨基- 在 genes from Klebsiella pneumoniae subsp. pneumoniae 作用下， 以 aq. buffer 为溶剂， 生成 5-氨基尿嘧啶
  参考文献：
  名称：

  Discovery of a Bacterial 5-Methylcytosine Deaminase

  摘要：

  5-Methylcytosine is found in all domains of life, but the bacterial cytosine deaminase from Escherichia coli (CodA) will not accept 5-methylcytosine as a substrate. Since significant amounts of 5-methylcytosine are produced in both prokaryotes and eukaryotes, this compound must eventually be catabolized and the fragments recycled by enzymes that have yet to be identified. We therefore initiated a comprehensive phylogenetic screen for enzymes that may be capable of deaminating 5-methylcytosine to thymine. From a systematic analysis of sequence homologues of CodA from thousands of bacterial species, we identified putative cytosine deaminases where a "discriminating" residue in the active site, corresponding to Asp-314 in CodA from E. coli, was no longer conserved. Representative examples from Klebsiella pneumoniae (locus tag: Kpn00632), Rhodobacter sphaeroides (locus tag: Rsp0341), and Corynebacterium glutamicum (locus tag: NCgl0075) were demonstrated to efficiently deaminate 5-methylcytosine to thymine with values of k(cat)/K-m of 1.4 x 10(5), 2.9 x 10(4), and 1.1 x 10(3) M-1 s(-1), respectively. These three enzymes also catalyze the deamination of 5-fluorocytosine to 5-fluorouracil with values of k(cat)/K-m of 1.2 x 10(5), 6.8 x 10(4), and 2.0 x 10(2) M-1 s(-1), respectively. The three-dimensional structure of Kpn00632 was determined by X-ray diffraction methods with 5-methylcytosine (PDB id: 4R85 ), 5-fluorocytosine (PDB id: 4R88 ), and phosphonocytosine (PDB id: 4R7W ) bound in the active site. When thymine auxotrophs of E. coli express these enzymes, they are capable of growth in media lacking thymine when supplemented with 5-methylcytosine. Expression of these enzymes in E. coli is toxic in the presence of 5-fluorocytosine, due to the efficient transformation to 5-fluorouracil.

  DOI：

  10.1021/bi5012767
• 作为产物：
  描述：

  6-氨基-5-硝基-2(1h)-嘧啶 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 以85%的产率得到2(1H)-嘧啶酮,5,6-二氨基-
  参考文献：
  名称：

  Regioselective addition of Grignard reagents to a 2-oxopurinium salt

  摘要：

  Treatment of 6-ethoxy-1,3,6,7-tetrahydro-1,3,7-tribanzyl-2H-purin-2-one with trimethyl-chlorosilane gave a stable tribenzylated 2-oxopurinium salt, which selectively added Grignard reagents in the 6-position. The structure of the adducts were established from long range HETCOR NMR experiments.

  DOI：

  10.1016/0040-4020(95)00080-r

文献信息

• Synthesis and Biological Evaluation of New Dipyridylpteridines, Lumazines, and Related Analogues
  作者：Zina A. A. Abbas、Najwa M. J. Abu-Mejdad、Zeenah W. Atwan、Najim A. Al-Masoudi

  DOI：10.1002/jhet.2651

  日期：2017.3

  methanolic ammonia under drastic conditions. Condensation of 2 or 29 with 2‐oxo‐2‐(thiophen‐2‐yl)acetaldehyde oxime (11) gave the 6‐(2‐thienyl)‐pteridine‐4‐one (12) and 5‐chloro‐2‐(2‐thienyl)pyrido[3,4‐b]pyrazine (31), respectively. All compounds were evaluated for their antiviral activity against the replication of HIV‐1 and HIV‐2 in MT‐4. Some of the synthesized compounds were tested against the bacterial

  4,5-二氨基嘧啶2和3与2,2ʹ-联吡啶（4）的缩合分别得到6,7-双（2-吡啶基）蝶啶-2-一类似物5和7。类似地，6,7-双（2-吡啶基）luamzine衍生物13，15，17，和23，从5,6-二氨基-2- thiopyrimidines反应合成13，14，和22与4，分别，而缩合4,5,6-三氨基嘧啶（25）或5,6-二氨基类似物26与4分别提供了4-氨基蝶啶类似物27和28。得到4-硫代类似物的新蝶啶和lumazines的硫杂化6，8，16，和24。用甲醇氨水处理6和8分别得到4-异is呤类似物9和10。用取代的苯甲酰氯将15烷基化，得到18和19，它们环化为噻唑并蝶啶衍生物20和21分别用多磷酸处理。或者，在剧烈条件下，用甲醇氨处理24，制得27。2或29与2-氧代-2-（噻吩-2-基）乙醛肟（11）的缩合得到6-（2-噻吩基）-哌啶-4-基（12）和5-氯-2-（- 2-噻吩基]吡啶并[3
• Heterocyclic Amplifiers of Phleomycin. VI. Some Phenylpurines, Phenylpteridines, Phenylquinazolines and Related Compounds
  作者：DJ Brown、K Mori

  DOI：10.1071/ch9850467

  日期：——

  Synthetic routes are described to a series of 2-, 6- and 8- phenylpurines , each with an appropriate S-or NH-linked side chain elsewhere in the molecule; to 2- and 4-phenylpteridines, each with a similar side chain and some with two additional C-methyl groups, to 2- and 4-phenylquinazolines, each equipped with an analogous side chain; and to two pyridinyl analogues of the above. Three of the above components are shown to have considerable activity as amplifiers of phleomycin -G in an in vitro bacterial system.

  本研究描述了一系列 2-、6-和 8-苯基嘌呤的合成路线，每种嘌呤在分子的其他部位都有适当的 S 或 NH 链接侧链；2-和 4-苯基蝶啶，每种蝶啶都有类似的侧链，有些蝶啶还带有两个额外的 C-甲基；2-和 4-苯基喹唑啉，每种喹唑啉都带有类似的侧链；以及上述喹唑啉的两种吡啶类似物。在体外细菌系统中，上述成分中的三种被证明具有相当高的活性，可作为 phleomycin -G 的扩增剂。
• Compound instability in dimethyl sulphoxide, case studies with 5-aminopyrimidines and the implications for compound storage and screening
  作者：Eliška Procházková、Petr Jansa、Anna Březinová、Lucie Čechová、Helena Mertlíková-Kaiserová、Antonín Holý、Martin Dračínský

  DOI：10.1016/j.bmcl.2012.08.065

  日期：2012.10

  The oxidation reactions of 5-aminopyrimidine derivatives in dimethyl sulphoxide (DMSO) were studied. The DMSO solutions of the studied compounds became deeply coloured within a few hours or days. The oxidation products can undergo further condensation reactions with the starting pyrimidines to yield bipyrimidines and/or pyrimidopteridines. The reaction mechanism of the oxidation-condensation reaction

  研究了5-氨基嘧啶衍生物在二甲基亚砜（DMSO）中的氧化反应。所研究化合物的DMSO溶液在数小时或数天内会变深。氧化产物可与起始嘧啶进行进一步的缩合反应，以产生联嘧啶和/或嘧啶蝶啶。5-氨基嘧啶与四氧嘧啶（2,4,5,6-四氧嘧啶）的反应也支持了氧化-缩合反应的反应机理。DMSO通常在生物活性的体外测试中用作溶剂，但它也是氧化剂，可能与溶质分子发生反应，并显着影响生成的生化数据的质量。
• Johnson; Johns; Heyl, American Chemical Journal, 1906, vol. 36, p. 176
  作者：Johnson、Johns、Heyl

  DOI：——

  日期：——
• Mapping the Landscape of Potentially Primordial Informational Oligomers: Oligodipeptides Tagged with 2,4-Disubstituted 5-Aminopyrimidines as Recognition Elements
  作者：Gopi Kumar Mittapalli、Yazmin M. Osornio、Miguel A. Guerrero、Kondreddi Ravinder Reddy、Ramanarayanan Krishnamurthy、Albert Eschenmoser

  DOI：10.1002/anie.200603209

  日期：2007.3.26

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