6-氨基-5-硝基-2(1H)-吡啶酮 | 211555-30-5

• 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-5-硝基-2(1H)-吡啶酮
• 英文名称: 6-amino-5-nitro-1H-pyridin-2-one
• 英文别名: 6-amino-5-nitro-2(1H)-pyridinone
• CAS: 211555-30-5
• 化学式: C₅H₅N₃O₃
• 分子量: 155.113
• InChiKey: JFGLOZOVAGYLKU-UHFFFAOYSA-N

物化性质

• 沸点：
  305.9±42.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 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

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  6-氨基-5-硝基-2(1H)-吡啶酮 在 palladium diacetate 、 N-碘代丁二酰亚胺 、 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 241.08h， 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 potassium acetate 、 乙酸酐 、 间氯过氧苯甲酸 作用下， 以 丙酮 为溶剂， 反应 92.25h， 生成 6-氨基-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

• Methods for Chk2 inhibitor patient selection
  申请人：Altieri Dario

  公开号：US20080125358A1

  公开（公告）日：2008-05-29

  The present invention contemplates a method to identify subjects that either have a tumor, or are at risk for tumor development, that are responsive to various inhibitors of an activated-Chk2 protein. Such Chk2 inhibitors may comprise a benzimidazole core structure, and derivatives thereof. Other Chk2 inhibitors may comprise nucleic acids, such as silencing interference RNA's specific for a Chk2 expression. Other Chk2 inhibitors may comprises proteins, such as antibodies. For example, the present invention contemplates that when a Chk2 inhibitor is administered during, or after, ionizing radiation tumor cell apoptosis is increased.

  本发明考虑了一种用于识别患有肿瘤或患有肿瘤风险、对激活的Chk2蛋白的各种抑制剂具有响应的受试者的方法。这些Chk2抑制剂可能包括苯并咪唑核结构及其衍生物。其他Chk2抑制剂可能包括核酸，例如特异于Chk2表达的沉默干扰RNA。其他Chk2抑制剂可能包括蛋白质，例如抗体。例如，本发明考虑了当在电离辐射期间或之后给予Chk2抑制剂时，肿瘤细胞凋亡增加。
• 一种5（4H）-吡啶酮并呋咱氧化物的合成方法
  申请人：盐城师范学院

  公开号：CN103936766B

  公开（公告）日：2016-09-14

  本发明公开了一种5（4H）‑吡啶酮并呋咱氧化物（III，又称4H，5H‑[1，2，5]噁二唑[3，4‑b]吡啶‑5‑酮‑1‑氧化物）的合成方法，包括如下步骤（见下反应式）：在一定温度下，将2‑氨基‑3‑硝基‑6‑氯吡啶（I）在含水的醇类溶液中与氟化钾（或钠等）反应；或者将I在丙酮中和亚硝酸盐反应，制得2‑氨基‑3‑硝基‑6‑羟基吡啶（II）；然后在碱性条件下，经氧化、缩合反应制得III。本发明的合成工艺简单，操作方便，适于较大规模生产III，为制备这类具有释放一氧化氮（NO）作用的抗病毒、抗肿瘤化合物提供了新途径。
• 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。
• Zinc-promoted direct amination of nitropyridines with methoxyamine via vicarious nucleophilic substitution
  作者：Shinzo Seko、Kunihito Miyake

  DOI：10.1039/a803497d

  日期：——

  Direct amination of nitropyridines with methoxyamine in the presence of a stoichiometric amount of zinc(II) chloride under basic conditions proceeds to give aminonitropyridines.

  在碱性条件下，硝基吡啶与甲氧基胺在一定量的氯化锌（II）存在下直接胺化，生成氨基硝基吡啶。
• Novel non-benzimidazole chk2 kinase inhibitors
  作者：Kelly J. McClure、Liming Huang、Kristen L. Arienti、Frank U. Axe、Anders Brunmark、Jon Blevitt、J. Guy Breitenbucher

  DOI：10.1016/j.bmcl.2005.12.096

  日期：2006.4

  In a recent paper, [Arienti, K. L.; Brunmark, A.; Axe, F. U.; McClure, K. M.; Lee, A.; Blevitt, J.; Neff, D. K.; Huang, L.; Crawford, S.; Chermagiri, R. P.; Karlsson, L.; Brietenbucher, J. G. J. Med. Chem. 2005, 48, 1873], we described the discovery of a class of benzimidazole chk2 kinase inhibitors, exemplified by compound 1, which had radio-protective effects in human T-cells subjected to ionizing radiation. Here, a series of non-benzimidazole analogs intended to define the scope of the SAR about this new series of inhibitor, and allow for refinement of the binding model of these compounds to the chk2 kinase is described. (C) 2006 Elsevier Ltd. All rights reserved.