8H-naphtho[1,2-g]pteridine-9,11-dione | 4707-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 8H-naphtho[1,2-g]pteridine-9,11-dione
• 英文别名: 8H-Naphtho[1,2-g]pteridin-9,11-dion；8H-naphtho[1,2-g]pteridine-9,11-dione
• CAS: 4707-30-6
• 化学式: C₁₄H₈N₄O₂
• 分子量: 264.243
• InChiKey: BAOZURWLCCLFQN-UHFFFAOYSA-N

物化性质

• 熔点：
  385 °C (decomp)
• 密度：
  1.501±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8H-naphtho[1,2-g]pteridine-9,11-dione 生成 1-[2'-deoxy-3',5'-di-O-(p-toluoyl)-α-D-ribofuranosyl]naphtho[1,2-g]pteridine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Pteridine Nucleosides—New Versatile Building Blocks in Oligonucleotide Synthesis

  摘要：

  Chemical syntheses of 1-(2-deoxy-beta-D-ribofuranosyl)lumazines and isopterins as well as 8-(2-deoxy-beta-D-ribofuranosyl)-4-amino-7(8H)pteridones and -isoxanthopterins have been developed to make the structural analogs of the naturally occurring 2'-deoxyribonucleosides in the pteridine series available. The corresponding phosphoramidites have been used in machine-aided solid-support syntheses leading to new types of fluorescence labeled oligonucleotides. The effects of the various fluorophors on duplex formation and as labels for enzyme reactions is demonstrated.

  DOI：

  10.1080/07328319708006188
• 作为产物：
  描述：

  (2-carbamoyl-benzo[f]quinoxalin-3-yl)-carbamic acid ethyl ester 在 sodium ethanolate 作用下， 生成 8H-naphtho[1,2-g]pteridine-9,11-dione
  参考文献：
  名称：

  Felton et al., Journal of the Chemical Society, 1954, p. 2895,2899

  摘要：

  DOI：

文献信息

• Nucleotides. Part LIV. Synthesis of condensedN1-(2?-deoxy-?-D-ribofuranosyl)lumazines, New fluorescent building blocks in oligonucleotide synthesis
  作者：Angelika Rosler、Wolfgang Pfleiderer

  DOI：10.1002/hlca.19970800611

  日期：1997.9.22

  3′-(2-cyanoethyI diisopropylphosphoramidites) 34–39 which function as monomeric building block in oligonucleotide syntheses as well as into the 3′-(hydrogen succinates) 40–45 which can be used for coupling with the solid-support material. A series of lumazine-modified oligonucleotides were synthesized and the influence of the new nucleobases on the stability of duplex formation studied by measuring the Tm values

  各种缩合areno [克] lumazine衍生物2，3，和5 - 7合成作为糖基化反应的新的荧光苷元与2-脱氧-3，5-二- Ö - （p甲苯甲酰）-α/β-D-在Hilbert - Johnson - Birkofer反应中，赤型-五氟呋喃糖酰氯（10）形成相应的N 1-（2'-deoxyribonucleosides）15 – 21。的βd端基异构体15，17，19，和21被解封为24 – 27，并与N 1-（2'-脱氧-β-D-呋喃呋喃糖基）lumazine（22）及其6，6，7-二苯基衍生物23一起在5'-位被二甲氧基三苯甲基化为28-33。然后将这些中间体转化成3' - （2- cyanoethyI diisopropylphosphoramidites）34 - 39，其功能如在寡核苷酸合成以及进3单体结构单元' - （氢琥珀酸酯）40 - 45可用于与固相支持材料偶联。合成
• Felton et al., Journal of the Chemical Society, 1954, p. 2895,2899
  作者：Felton et al.

  DOI：——

  日期：——
• Pteridine Nucleosides—New Versatile Building Blocks in Oligonucleotide Synthesis
  作者：Ramamurthy Charubala、Juris Maurinsh、Angelika Rösler、Manuel Melguizo、Oliver Jungmann、Margarete Gottlieb、Jörg Lehbauer、Mary Hawkins、Wolfgang Pfleiderer

  DOI：10.1080/07328319708006188

  日期：1997.7

  Chemical syntheses of 1-(2-deoxy-beta-D-ribofuranosyl)lumazines and isopterins as well as 8-(2-deoxy-beta-D-ribofuranosyl)-4-amino-7(8H)pteridones and -isoxanthopterins have been developed to make the structural analogs of the naturally occurring 2'-deoxyribonucleosides in the pteridine series available. The corresponding phosphoramidites have been used in machine-aided solid-support syntheses leading to new types of fluorescence labeled oligonucleotides. The effects of the various fluorophors on duplex formation and as labels for enzyme reactions is demonstrated.