2-amino-6-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4(3H)-one | 341981-72-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-6-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4(3H)-one
• 英文别名: 2-amino-6-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one；2-amino-6-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one
• CAS: 341981-72-4
• 化学式: C₁₁H₁₄N₄O₅
• 分子量: 282.256
• InChiKey: BKUKJCDLKLFEJB-XUTVFYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  153
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-6-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4(3H)-one 在 吡啶 、 三甲基氯硅烷 作用下， 反应 6.0h， 生成 2-isobutyrylamino-6-[3,5-(1,1,3,3-tetraisopropyl-1,3-disiloxan-1,3-yl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  7-脱氮鸟嘌呤的C（8）-（2'-脱氧β-D-核糖呋喃糖苷）：具有异常连接的核碱基的寡核苷酸的合成和碱基配对。

  摘要：

  具有不寻常糖基化位点的7-脱氮鸟嘌呤（2-氨基吡咯并[2,3-d]嘧啶-4-酮）C（8）-（2'-脱氧β-D-核呋喃糖苷）（6b）为合成并掺入寡核苷酸。使用亚磷酰胺化学通过固相合成制备寡核苷酸，并将其杂交以形成双链DNA。化合物6b能够在具有反平行链方向的寡核苷酸双链体中与2'-脱氧-5-甲基异胞苷（m（5）isoC（d））形成碱基对，并在平行双链体DNA中与dC形成碱基对。因此，C（8）-核苷6b显示出与2'-脱氧异鸟苷类似的碱基识别，但与2'-脱氧鸟苷不同。这表明核酸识别不仅取决于核碱基的供体-受体模式，而且受糖基化位点影响。

  DOI：

  10.1021/jo001498q
• 作为产物：
  描述：

  1-乙酰基-三-苄氧基-罗伯糖 在 sodium methylate 、 四氯化锡 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 3.0h， 生成 2-amino-6-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4(3H)-one
  参考文献：
  名称：

  Direct C-glycosylation of guanine analogs: the synthesis and antiviral activity of certain 7- and 9-deazaguanine C-nucleosides

  摘要：

  C-Glycosylation of two guanine analogues, 9-deaza- and 7-deazaguanine, has been achieved under Friedel-Crafts conditions, providing a direct synthetic route to 9-deazaguanosine (4; 2-amino-7-beta-D-ribofuranosyl-5H-pyrrolo[3,2-d]pyrimidin-4(3H)-one) and 8-beta-D-ribofuranosyl-7-deazaguanine (16), respectively. This electrophilic C-glycosylation was applied successfully to six guanine and substituted-guanine analogues resulting in yields of approximately 50%. This represents the first reported C-ribosylation of preformed nitrogen heterocycles isosteric with guanine. These C-nucleosides were evaluated for their ability to provide protection against a lethal Semliki Forest virus infection in mice, relative to 7-thia-8-oxoguanosine which was used as a positive control. Two of the C-nucleosides, 2-amino-6-chloro-5-methyl-7-beta-D-ribofuranosyl-5H-pyrrolo [3,2-d]pyrimidin-4(3H)-one (12) and the corresponding 6-bromo derivative (13), showed good prophylactic activity in this virus model system.

  DOI：

  10.1021/jm00172a011

文献信息

• N8- and C8- linked purine bases as universal nucleosides used for oligonucleotide hybridization
  申请人：Roche Diagnostics GmbH

  公开号：EP1138688A1

  公开（公告）日：2001-10-04

  The present invention is directed to a nucleic acid binding compound comprising N8- or C8-linked purine bases or structurally related heterocycles, a compound useful for the preparation of such compound, a binding product of this nucleic acid binding compound with a nucleic acid, a method for the determination of a nucleic acid using said compound, and several uses of 8-linked purine bases and structurally related heterocycles. Compounds according to the present invention have advantageous properties when used in hybridization methods.

  本发明涉及一种核酸结合化合物，该化合物包含 N8-或 C8-连接的嘌呤碱基或结构相关的杂环，一种用于制备这种化合物的化合物，这种核酸结合化合物与核酸的结合产物，一种使用所述化合物测定核酸的方法，以及 8-连接的嘌呤碱基和结构相关的杂环的几种用途。根据本发明的化合物在杂交方法中使用时具有优势特性。
• N8- and C8-linked purine bases as universal nucleosides used for oligonucleotide hybridization
  申请人：Roche Diagnostics GmbH

  公开号：EP1138689A1

  公开（公告）日：2001-10-04

  The present invention is directed to a nucleic acid binding compound comprising N8- or C8-linked purine bases or structurally related heterocycles, a compound useful for the preparation of such compound, a binding product of this nucleic acid binding compound with a nucleic acid, a method for the determination of a nucleic acid using said compound, and several uses of 8-linked purine bases and structurally related heterocycles. Compounds according to the present invention have advantageous properties when used in hybridization methods.

  本发明涉及一种核酸结合化合物，该化合物包含 N8-或 C8-连接的嘌呤碱基或结构相关的杂环，一种用于制备这种化合物的化合物，这种核酸结合化合物与核酸的结合产物，一种使用所述化合物测定核酸的方法，以及 8-连接的嘌呤碱基和结构相关的杂环的几种用途。根据本发明的化合物在杂交方法中使用时具有优势特性。
• N8-and c8-linked purine based and structurally related heterocycles as universal nucleosides used oligonucleotides hybridization
  申请人：——

  公开号：US20040171820A1

  公开（公告）日：2004-09-02

  The present invention is directed to a nucleic acid binding compound comprising N 8 - or C 8 -linked purine bases or structurally related heterocycles, a compound useful for the preparation of such compound, a binding product of this nucleic acid binding compound with a nucleic acid, a method for the determination of a nucleic acid using said compound, and several uses of 8-linked purine bases and structurally related heterocycles. Compounds according to the present invention have advantageous properties when used in hybridization methods.

  本发明涉及一种核酸结合化合物，它包含 N 8 - 或 C 8 -连接的嘌呤碱基或结构相关的杂环的核酸结合化合物、一种可用于制备这种化合物的化合物、这种核酸结合化合物与核酸的结合产物、一种使用所述化合物测定核酸的方法，以及8-连接的嘌呤碱基和结构相关的杂环的几种用途。根据本发明的化合物在杂交方法中使用时具有优势特性。
• N8- and C8-linked purine bases and structurally related heterocycles as universal nucleosides used for oligonucleotides hybridization
  申请人：Seela Frank

  公开号：US20060135462A1

  公开（公告）日：2006-06-22

  The present invention is directed to a nucleic acid binding compound comprising N 8 - or C 8 -linked purine bases or structurally related heterocycles, a compound useful for the preparation of such compound, a binding product of this nucleic acid binding compound with a nucleic acid, a method for the determination of a nucleic acid using said compound, and several uses of 8-linked purine bases and structurally related heterocycles. Compounds according to the present invention have advantageous properties when used in hybridization methods.

  本发明涉及一种核酸结合化合物，它包含 N 8 - 或 C 8 -连接的嘌呤碱基或结构相关的杂环的核酸结合化合物、一种可用于制备这种化合物的化合物、这种核酸结合化合物与核酸的结合产物、一种使用所述化合物测定核酸的方法，以及8-连接的嘌呤碱基和结构相关的杂环的几种用途。根据本发明的化合物在杂交方法中使用时具有优势特性。
• GIRGIS, NABIH S.;MICHAEL, MAGED A.;SMEE, DONALD F.;ALAGHAMANDAN, HASSAN A+, J. MED. CHEM., 33,(1990) N0, C. 2750-2755
  作者：GIRGIS, NABIH S.、MICHAEL, MAGED A.、SMEE, DONALD F.、ALAGHAMANDAN, HASSAN A+

  DOI：——

  日期：——