4-甲氧基-2,2'-联吡啶氮氧化物 | 14163-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-甲氧基-2,2'-联吡啶氮氧化物
• 英文名称: 4-methoxy-2,2’-bipyridine N-oxide
• 英文别名: 4-methoxy-[2,2']bipyridinyl N-oxide；4-methoxy-2,2'-bipyridine N-oxide；4-Methoxy-2,2'-bipyridyl N-Oxide；4-methoxy-2,2'-bipyridyl 1-oxide；4-methoxy-[2,2']bipyridinyl 1-oxide；4-Methoxy-[2,2'-bipyridine]1-oxide；4-methoxy-1-oxido-2-pyridin-2-ylpyridin-1-ium
• CAS: 14163-05-4
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: RXPZDZCWNPJLKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C
• 沸点：
  441.2±30.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲氧基-2,2'-联吡啶氮氧化物 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以94%的产率得到6-iodo-4-methoxy-2,2'-bipyridine N-oxide
  参考文献：
  名称：

  First Syntheses of Caerulomycin E and Collismycins A and C. A New Synthesis of Caerulomycin A

  摘要：

  Caerulomycins produced by Streptomyces caeruleus, and collismycins more recently isolated from Streptomyces species, are bipyridinic molecules endowed with antibiotic and cytotoxic activities. The first syntheses of caerulomycin E (1), as well as new syntheses of caerulomycin A (2), are reported. Methodologies involving efficiently controlled reactions such as metalation and cross-coupling reactions have been developed from 2,2'-bipyridine. The functionalization at C-6 could be achieved by metalation of 2,2'-bipyridine N-oxides 5 and 12. 6-Halo-4-methoxy-2,2'-bipyridines (6, 10, 11) became key-molecules of these different pathways, and further functionalization at C-5 allowed the first syntheses of collismycins A (3) and C (4).

  DOI：

  10.1021/jo972022i
• 作为产物：
  描述：

  2,2′-二吡啶基 N-氧化物 在 硫酸 、 potassium nitrate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 4-甲氧基-2,2'-联吡啶氮氧化物
  参考文献：
  名称：

  First Syntheses of Caerulomycin E and Collismycins A and C. A New Synthesis of Caerulomycin A

  摘要：

  Caerulomycins produced by Streptomyces caeruleus, and collismycins more recently isolated from Streptomyces species, are bipyridinic molecules endowed with antibiotic and cytotoxic activities. The first syntheses of caerulomycin E (1), as well as new syntheses of caerulomycin A (2), are reported. Methodologies involving efficiently controlled reactions such as metalation and cross-coupling reactions have been developed from 2,2'-bipyridine. The functionalization at C-6 could be achieved by metalation of 2,2'-bipyridine N-oxides 5 and 12. 6-Halo-4-methoxy-2,2'-bipyridines (6, 10, 11) became key-molecules of these different pathways, and further functionalization at C-5 allowed the first syntheses of collismycins A (3) and C (4).

  DOI：

  10.1021/jo972022i

文献信息

• Palladium-Catalyzed Directed Halogenation of Bipyridine <i>N</i>-Oxides
  作者：Sina P. Zucker、Friedrich Wossidlo、Manuela Weber、Dieter Lentz、C. Christoph Tzschucke

  DOI：10.1021/acs.joc.7b00444

  日期：2017.6.2

  The palladium-catalyzed directed C–H halogenation of bipyridine N-oxides was investigated. Using NCS or NBS (N-chloro- or N-bromosuccinimide) and 5 mol % Pd(OAc)2 in chlorobenzene (0.10 molar) at 110 °C, pyridine-directed functionalization took place and 3-chloro- or 3-bromobipyridine N-oxides were obtained in high yields. The reaction is sensitive to steric hindrance by 4- and 6′-substituents. Only

  研究了钯催化的联吡啶N-氧化物的直接CH卤代反应。在110°C下使用NCS或NBS（N-氯-或N-溴代琥珀酰亚胺）和5 mol％Pd（OAc）2在氯苯中（0.10摩尔），进行吡啶定向的官能化反应，生成3-氯-或3-溴代联吡啶N -氧化物以高收率获得。该反应对4-和6'-取代基的空间位阻敏感。仅在后一种情况下，吡啶与钯的配位受阻，才观察到由N-氧化物官能团引导的3'-卤化。卤化产物通过PCl 3或PBr 3脱氧。
• USE OF COLLISMYCIN AND DERIVATIVES THEREOF AS OXIDATIVE STRESS INHIBITORS
  申请人：Martinez Gil Ana

  公开号：US20100048635A2

  公开（公告）日：2010-02-25

  The present invention relates to the use of Collismycin and derivatives thereof as inhibitors of oxidative stress in cells and their use for the preparation of medicaments for the treatment and/or prevention of oxidative stress-induced diseases or conditions, especially neurodegenerative diseases, such as Alzheimer's Disease and Parkinson's Disease.

  本发明涉及使用Collismycin及其衍生物作为细胞内氧化应激的抑制剂，以及它们用于制备治疗和/或预防氧化应激引起的疾病或病状的药物，尤其是神经退行性疾病，如阿尔茨海默病和帕金森病。
• Use of Collismycin and Derivatives Thereof as Oxidative Stress Inhibitors
  申请人：Martinez Gil Ana

  公开号：US20080275088A1

  公开（公告）日：2008-11-06

  The present invention relates to the use of Collismycin and derivatives thereof as inhibitors of oxidative stress in cells and their use for the preparation of medicaments for the treatment and/or prevention of oxidative stress-induced diseases or conditions, especially neurodegenerative diseases, such as Alzheimer's Disease and Parkinson's Disease.

  本发明涉及使用Collismycin及其衍生物作为细胞内氧化应激抑制剂及其用于制备治疗和/或预防氧化应激引起的疾病或症状的药物，特别是神经退行性疾病，如阿尔茨海默病和帕金森病。
• Use of collismycin and derivatives thereof as oxidative stress inhibitors
  申请人：Neuropharma S.A.

  公开号：EP1749552A1

  公开（公告）日：2007-02-07

  The present invention relates to the use of Collismycin and derivatives thereof as inhibitors of oxidative stress in cells and their use for the preparation of medicaments for the treatment of oxidative stress-induced diseases or conditions, specially neurodegenerative diseases, such as Alzheimer's Disease and Parkinson's Disease.

  本发明涉及科利霉素及其衍生物作为细胞氧化应激抑制剂的用途，以及它们用于制备治疗氧化应激引起的疾病或病症的药物，特别是神经退行性疾病，如阿尔茨海默氏症和帕金森氏症。
• 联吡啶类化合物、其可药用的盐以及制备方法和应用
  申请人：杭州科兴生物化工有限公司

  公开号：CN116751195A

  公开（公告）日：2023-09-15

  本发明公开了一类联吡啶类化合物或其可药用的盐，以及制备方法和在医药上的应用。本发明还公开了该类型具体46个化合物及其化学合成方法，合成路线简单，易于操作和实施，并且所需试剂易于购买。同时测试了46个化合物对9种肿瘤细胞的增殖抑制活性，结果显示相比于此类天然产物的增殖抑制活性的30μM(IC50)，化合物的增殖抑制活性有了极大的提高，经过结构修饰之后活性可以达到几十至几百纳摩尔。另外，多个化合物的对多种癌细胞的增殖活性优于阿霉素的作用效果，与5‑氟尿嘧啶结果相当，可以作为多种癌症相关疾病的治疗药物，也可作为蛋白抑制剂用于治疗相关疾病或病症的用途。