7-methyl-10-oxo-9,10-dihydropyrimido[1,2-a]purine | 57325-61-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 7-methyl-10-oxo-9,10-dihydropyrimido[1,2-a]purine
• 英文别名: 7-Methylpyrimido<1,2-a>purin-10(3H)-one；7-methylpyrimido[1,2-a]purin-10(3H)-one；7-methyl-10-oxo-9,10-dihydropyrimido<1,2-a>purine；7-methyl-1H-pyrimido[1,2-a]purin-10-one
• CAS: 57325-61-8
• 化学式: C₉H₇N₅O
• 分子量: 201.187
• InChiKey: ZWFWEQKXMCRJPR-UHFFFAOYSA-N

物化性质

• 沸点：
  535.5±42.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methyl-10-oxo-9,10-dihydropyrimido[1,2-a]purine 在 sodium hydroxide 、 potassium carbonate 作用下， 反应 16.0h， 生成 9-(4-羟基丁基)鸟嘌呤
  参考文献：
  名称：

  Studies on the Alkylation of Guanine. 2. The Synthesis of Acyclic Guanosine Analogs via the Precursor 7-Methyl-10-oxo-9,10-dihydropyrimido[1,2-a]purine.

  摘要：

  DOI：

  10.3891/acta.chem.scand.40b-0310
• 作为产物：
  描述：

  4--5-imidazolecarboxamide 在 盐酸 、 manganese(IV) oxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.17h， 生成 7-methyl-10-oxo-9,10-dihydropyrimido[1,2-a]purine
  参考文献：
  名称：

  Confirmation of the structure of the guanine-methylmalondialdehyde reaction product by unequivocal synthesis

  摘要：

  DOI：

  10.1021/jo00317a037

文献信息

• Syntheses of 7-(2-Hydroxy-1-phenylethyl)- and 7-(2-Hydroxy-2-phenylethyl)guanine, DNA Adducts Derived from Styrene 7,8-Oxide
  作者：Jan Novák、Igor Linhart、Hana Dvorˇáková

  DOI：10.1002/ejoc.200300811

  日期：2004.6

  7-(2-Hydroxy-1-phenylethyl)- and 7-(2-hydroxy-2-phenylethyl)guanines are important DNA adducts which can be used as markers of exposure to styrene. Two synthetic routes leading to these compounds are presented using allyl-protected bromohydrins as synthetic equivalents of styrene oxide to alkylate 2-amino-6-chloropurine or 7-methyl-10-oxo-9,10-dihydropyrimido[1,2-a]purine as precursors to guanine. (© Wiley-VCH

  7-(2-羟基-1-苯乙基)-和7-(2-羟基-2-苯乙基)鸟嘌呤是重要的DNA加合物，可用作暴露于苯乙烯的标记。使用烯丙基保护的溴醇作为氧化苯乙烯的合成等效物来烷基化 2-amino-6-chloropurine 或 7-methyl-10-oxo-9,10-dihydropyrimido[1,2-a] 提出了导致这些化合物的两种合成路线嘌呤是鸟嘌呤的前体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Pyrimido[1,2-<i>α</i>]purin-10(3<i>H</i>)-one:  A Reactive Electrophile in the Genome
  作者：Nathalie Schnetz-Boutaud、J. Scott Daniels、Muhammed F. Hashim、Peter Scholl、Tamika Burrus、Lawrence J. Marnett

  DOI：10.1021/tx000135i

  日期：2000.10.1

  Previous studies have shown that tris(hydroxymethyl)aminomethane adds to 1 at elevated pH, forming an enaminoimine (2), but it is uncertain whether 1 reacts directly or hydrolyzes under basic conditions to N(2)-(3-oxo-1-propenyl)deoxyguanosine (3) prior to amine addition. We report that 1 reacts at neutral pH with hydroxylamines to form oximes. The rate of reaction of 1 with hydroxylamines at pH 7 is

  丙二醛和基础丙二醛与DNA中的脱氧鸟嘌呤残基反应形成环外加合物，嘧啶并[1，2-α嘌呤-10（3H）-一（1），已在健康人的基因组DNA中以高水平检测到。先前的研究表明，三（羟甲基）氨基甲烷在pH升高时会添加到1中，形成一个烯氨基亚胺（2），但尚不确定1是否在碱性条件下直接反应或水解成N（2）-（3-oxo-1-胺加成前先用丙烯基）脱氧鸟苷（3）。我们报告1在中性pH下与羟胺反应形成肟。1与羟胺在pH 7下的反应速率比1至3的水解速率至少快150倍。因此，1与亲核试剂直接反应。
• New Approach to the Synthesis of<i>N</i>⁷-Arylguanines and<i>N</i>⁷-Aryladenines
  作者：Roman Keder、Hana Dvořáková、Dalimil Dvořák

  DOI：10.1002/ejoc.200801002

  日期：2009.4

  The copper-mediated arylation of 7-methylpyrimido[1,2-a]purin-10(3H)-one (1) in dichloromethane or of N2-(dimethylamino)methyleneguanine (2) in methanol in the presence of TMEDA as a base/ligand led to the preferential formation of 1-aryl-7-methylpyrimido[1,2-a]purin-10(3H)-ones (4) and 7-aryl-N2-(dimethylamino)methyleneguanines (7), respectively. These compounds can be easily hydrolysed to the corresponding

  铜介导的 7-甲基嘧啶并 [1,2-a]purin-10(3H)-one (1) 在二氯甲烷中或 N2-(二甲氨基)亚甲基鸟嘌呤 (2) 在甲醇中在 TMEDA 作为碱存在下的芳基化/配体分别导致优先形成 1-芳基-7-甲基嘧啶并[1,2-a]嘌呤-10(3H)-酮 (4) 和 7-芳基-N2-(二甲氨基) 亚甲基鸟嘌呤 (7)。这些化合物可以很容易地水解成相应的 7-芳基鸟嘌呤。在邻菲咯啉而不是 TMEDA 存在下，N6-（二甲氨基）亚甲基腺嘌呤 (15) 的类似芳基化反应在水解后主要提供 7-芳基腺嘌呤。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009）
• Pentenyl ribosides: new reagents for purine nucleoside synthesis
  作者：Marie Christine Chapeau、Lawrence J. Marnett

  DOI：10.1021/jo00077a057

  日期：1993.12

  Protected pent-4-enyl ribosides and deoxyribosides were synthesized as reagents for the preparation of nucleosides and deoxynucleosides. Reaction of pent-4-enyl 2',3',5'-tri-O-benzoyl-D-erythro-pentofuranoside with five nucleobases in the presence of N-iodosuccinimide/trifluoromethanesulfonic acid (NIS/TfOH) produced the N-9-beta-nucleosides in 50-70% yields. Pent-4-enyl-2-deoxy-3',5'-di-O-p-toluyl-alpha-D-erythro-pentofuranoside coupled with 6-chloropurine in the presence of iodonium dicollidine perchlorate (IDCP) to produce a mixture of deoxynucleoside isomers (N-9, N-7, alpha,beta) in 91% yield. Under the same conditions, coupling of 6-chloropurine with pent-4-enyl 2'-deoxy-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-D-erythro-pentofuranoside produced only N-9alpha and N-9beta products in 40% total yield. The N-9beta nucleoside was the only product of the reaction of 6-chloropurine with pent-4-enyl 2'-O-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-D-erythro-pentofuranoside in the presence of NIS/TfOH. Pent-4-enyl ribosides appear to be useful reagents for the synthesis of ribo- and deoxyribonucleosides under mild (NIS/TfOH) or neutral (IDCP) conditions.
• KJELLBERG, J.;HAGBERG, C. -E.;MALM, A.;NOREN, J. O.;JOHANSSON, N. G., ACTA CHEM. SCAND., 1986, 40, N 4, 310-312
  作者：KJELLBERG, J.、HAGBERG, C. -E.、MALM, A.、NOREN, J. O.、JOHANSSON, N. G.

  DOI：——

  日期：——