6-氨基-3-碘-5-硝基-2(1H)-吡啶酮 | 642460-96-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 6-氨基-3-碘-5-硝基-2(1H)-吡啶酮
• 英文名称: 6-amino-3-iodo-5-nitro-1H-pyridin-2-one
• 英文别名: 2-amino-3-nitro-5-iodo-6-(1H)-pyridinone
• CAS: 642460-96-6
• 化学式: C₅H₄IN₃O₃
• 分子量: 281.01
• InChiKey: YPSCFDIDAMTMKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 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：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-氨基-3-碘-5-硝基-2(1H)-吡啶酮 在 palladium diacetate 、 四丁基氟化铵 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 145.08h， 生成 6-amino-5-nitro-3-(1'-β-D-2'-deoxyribofuranosyl)-2(1H)-pyridone
  参考文献：
  名称：

  Expanding the Genetic Alphabet:  Non-Epimerizing Nucleoside with the pyDDA Hydrogen-Bonding Pattern

  摘要：

  6-Amino-3-(2'-deoxy-beta-D-ribofuranosyl)-5-nitro-1H-pyridin-2-one (4), a C-glycoside exhibiting the nonstandard pgammaDDA hydrogen-bonding pattern, was synthesized via Heck coupling. The nitro group greatly enhances the stability of the nucleoside toward acid-catalyzed epimerization without leading to significant deprotonation of the heterocycle at physiological pH. These results make nucleoside 4 a promising candidate for an expanded genetic alphabet.

  DOI：

  10.1021/jo034900k
• 作为产物：
  描述：

  2-氨基-3-硝基吡啶 在 N-碘代丁二酰亚胺 、 potassium acetate 、 乙酸酐 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 188.25h， 生成 6-氨基-3-碘-5-硝基-2(1H)-吡啶酮
  参考文献：
  名称：

  Expanding the Genetic Alphabet:  Non-Epimerizing Nucleoside with the pyDDA Hydrogen-Bonding Pattern

  摘要：

  6-Amino-3-(2'-deoxy-beta-D-ribofuranosyl)-5-nitro-1H-pyridin-2-one (4), a C-glycoside exhibiting the nonstandard pgammaDDA hydrogen-bonding pattern, was synthesized via Heck coupling. The nitro group greatly enhances the stability of the nucleoside toward acid-catalyzed epimerization without leading to significant deprotonation of the heterocycle at physiological pH. These results make nucleoside 4 a promising candidate for an expanded genetic alphabet.

  DOI：

  10.1021/jo034900k

文献信息

• Non-standard nucleoside analogs with reduced epimerization
  申请人：——

  公开号：US08053212B1

  公开（公告）日：2011-11-08

  This invention relates to nucleoside, nucleotide, and oligonucleotide analogs that incorporate non-standard nucleobase analogs, defined to be those that present a pattern of hydrogen bonds to a paired nucleobase analog in a complementary strand that is different from the pattern presented by adenine, guanine, cytosine, and thymine. The invention is specifically concerned with compositions of matter that present the donor-donor-acceptor, donor-acceptor-donor, and acceptor-donor-donor non-standard hydrogen bonding patterns on pyrimidine analogs, where nucleoside analogs bearing these pyrimidine analogs do not epimerize as easily as those known in the art. The heterocycles on these nucleoside analogs are diaminopyridines and aminopyridones that have electron withdrawing groups attached to the position analogous to the 5-position of the ring in standard pyrimidines, including nitro, cyano, and carboxylic acid derivatives.

  这项发明涉及核苷酸、核苷酸和寡核苷酸类似物，其包含非标准核碱类似物，定义为这些类似物与互补链中的配对核碱类似物呈现的氢键模式不同于腺嘌呤、鸟嘌呤、胞嘧啶和胸腺嘧啶呈现的模式。该发明特别涉及呈现供体-供体-受体、供体-受体-供体和受体-供体-供体非标准氢键模式的嘧啶类似物的物质组合，其中带有这些嘧啶类似物的核苷类似物不像已知的那样容易发生对映异构。这些核苷类似物上的杂环是二氨基吡啶和氨基吡啶酮，它们带有连接到与标准嘧啶环中的5-位置类似的位置的电子吸引基团，包括硝基、氰基和羧酸衍生物。
• [EN] COMPOSITIONS FOR EDITING MECP2 TRANSCRIPTS AND METHODS THEREOF<br/>[FR] COMPOSITIONS POUR L'ÉDITION DE TRANSCRITS MECP2 ET PROCÉDÉS ASSOCIÉS
  申请人：[en]WAVE LIFE SCIENCES LTD.

  公开号：WO2023049477A2

  公开（公告）日：2023-03-30

  Among other things, the present disclosure provides oligonucleotides, compositions and methods thereof that can bring about specific editing of a target adenosine in a target RNA molecule. Such oligonucleotides, compositions and methods are useful to treat, prevent, or ameliorate MECP2 associated disorders, diseases and syndromes that can benefit from adenosine modification.
• Expanding the Genetic Alphabet:  Non-Epimerizing Nucleoside with the <i>py</i>DDA Hydrogen-Bonding Pattern
  作者：Daniel Hutter、Steven A. Benner

  DOI：10.1021/jo034900k

  日期：2003.12.1

  6-Amino-3-(2'-deoxy-beta-D-ribofuranosyl)-5-nitro-1H-pyridin-2-one (4), a C-glycoside exhibiting the nonstandard pgammaDDA hydrogen-bonding pattern, was synthesized via Heck coupling. The nitro group greatly enhances the stability of the nucleoside toward acid-catalyzed epimerization without leading to significant deprotonation of the heterocycle at physiological pH. These results make nucleoside 4 a promising candidate for an expanded genetic alphabet.