3-[(4-fluorophenyl)amino]-4-nitropyridin-1-ium-1-olate | 99822-90-9

• 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
• 英文名称: 3-[(4-fluorophenyl)amino]-4-nitropyridin-1-ium-1-olate
• 英文别名: 3-((4-Fluorophenyl)amino)-4-nitropyridine 1-oxide；N-(4-fluorophenyl)-4-nitro-1-oxidopyridin-1-ium-3-amine
• CAS: 99822-90-9
• 化学式: C₁₁H₈FN₃O₃
• 分子量: 249.201
• InChiKey: URCTUTMZCTWEHB-UHFFFAOYSA-N

物化性质

• 熔点：
  223 °C (decomp)
• 沸点：
  481.8±40.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(4-fluorophenyl)amino]-4-nitropyridin-1-ium-1-olate 在 水 、 铁粉 、 potassium carbonate 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 0.08h， 生成 N-[3-(4-fluorophenylamino)pyridin-4-yl]trifluoromethanesulfonamide
  参考文献：
  名称：

  N-(3-Arylaminopyridin-4-yl)alkanesulfonamides as pyridine analogs of nimesulide: Cyclooxygenases inhibition, anti-inflammatory studies and insight on metabolism

  摘要：

  Nimesulide, a COX-2 preferential inhibitor with a favorable gastric and cardiovascular safety profile, was responsible for some cases of acute liver failure attributed to the nitrobenzene ring. A series of analogs of nimesulide resulting from isosteric replacement of the nitrobenzene ring by the pyridine nucleus, was synthesized and their ability to inhibit both cyclooxygenases (COXs) isoforms was evaluated in vitro using a human whole blood model. Compounds 19c, 23b and 23c displayed an important inhibitory activity associated to a COX-2/COX-1 selectivity ratio similar to or higher than that of celecoxib. The anti-inflammatory activity and the ability of several compounds to decrease leukocyte infiltration were further evaluated in vivo in a model of a X carrageenan-induced pleurisy. Plasma assays were performed on blood samples collected from rats and allowed us to identify the 4-position of the phenyl ring as a major metabolism site explaining the occasionally observed lack of correlation between in vitro and in vivo results. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.033
• 作为产物：
  描述：

  3-溴吡啶-N-氧化物 在 吡啶 、 硫酸 、 硝酸 作用下， 生成 3-[(4-fluorophenyl)amino]-4-nitropyridin-1-ium-1-olate
  参考文献：
  名称：

  N-(3-Arylaminopyridin-4-yl)alkanesulfonamides as pyridine analogs of nimesulide: Cyclooxygenases inhibition, anti-inflammatory studies and insight on metabolism

  摘要：

  Nimesulide, a COX-2 preferential inhibitor with a favorable gastric and cardiovascular safety profile, was responsible for some cases of acute liver failure attributed to the nitrobenzene ring. A series of analogs of nimesulide resulting from isosteric replacement of the nitrobenzene ring by the pyridine nucleus, was synthesized and their ability to inhibit both cyclooxygenases (COXs) isoforms was evaluated in vitro using a human whole blood model. Compounds 19c, 23b and 23c displayed an important inhibitory activity associated to a COX-2/COX-1 selectivity ratio similar to or higher than that of celecoxib. The anti-inflammatory activity and the ability of several compounds to decrease leukocyte infiltration were further evaluated in vivo in a model of a X carrageenan-induced pleurisy. Plasma assays were performed on blood samples collected from rats and allowed us to identify the 4-position of the phenyl ring as a major metabolism site explaining the occasionally observed lack of correlation between in vitro and in vivo results. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.033

文献信息

• [EN] IMIDAZO[4,5-C]PYRIDINE AND PYRROLO[2,3-C]PYRIDINE DERIVATIVES AS SSAO INHIBITORS<br/>[FR] DÉRIVÉS D'IMIDAZO[4,5-C]PYRIDINE ET DE PYRROLO[2,3-C]PYRIDINE EN TANT QU'INHIBITEURS SSAO
  申请人：PROXIMAGEN LTD

  公开号：WO2014140592A1

  公开（公告）日：2014-09-18

  The compounds of formula (I) are inhibitors of semicarbazide- sensitive amine oxidase (SSAO) activity useful in the treatment of inflammation, an inflammatory disease, an immune or an autoimmune disorder, or inhibition of tumour growth.

  式(I)的化合物是半羧肼敏感胺氧化酶（SSAO）活性的抑制剂，可用于治疗炎症、炎症性疾病、免疫或自身免疫性疾病，或抑制肿瘤生长。
• NEW COMPOUNDS
  申请人：Proximagen Limited

  公开号：US20150258101A1

  公开（公告）日：2015-09-17

  The present invention provides certain compounds according to formula (I) which are inhibitors of SSAO activity wherein V, W, X, Y, Z, R 1 and R 2 are as defined in the specification.

  本发明提供了一些按照式(I)的化合物，这些化合物是SSAO活性的抑制剂，其中V、W、X、Y、Z、R1和R2如规范中所定义。
• [EN] IMIDAZO[4,5-C]PYRIDINE DERIVED SSAO INHIBITORS<br/>[FR] INHIBITEUR DE SSAO DÉRIVÉ D'IMIDAZO[4,5-C]PYRIDINE
  申请人：PROXIMAGEN LTD

  公开号：WO2016042331A1

  公开（公告）日：2016-03-24

  A compound as set out in claim 1, and the use of the same in therapy.

  权利要求1中所述的化合物，以及将其用于治疗。
• [EN] IMIDAZO[4,5-C]PYRIDINE DERIVED SSAO INHIBITORS<br/>[FR] INHIBITEURS D'UNE SSAO DÉRIVÉS D'UNE IMIDAZO[4,5-C]PYRIDINE
  申请人：PROXIMAGEN LTD

  公开号：WO2016042332A1

  公开（公告）日：2016-03-24

  A compound of formula (I) or a pharmaceutically acceptable salt, or N-oxide thereof and the use of the same in therapy: wherein Z, Y, R1, W, V, and R3 are as defined in claim 1.

  化合物的公式（I）或其药用盐，或N-氧化物及其在治疗中的应用：其中Z、Y、R1、W、V和R3如权利要求1中定义的。
• [EN] NEW THERAPEUTIC USES OF COMPOUNDS<br/>[FR] NOUVELLES UTILISATIONS THÉRAPEUTIQUES DE COMPOSÉS
  申请人：PROXIMAGEN LLC

  公开号：WO2021195406A1

  公开（公告）日：2021-09-30

  The present invention relates to the treatment and prevention of pulmonary inflammation using a compound of Formula (I) or a pharmaceutically acceptable salt, solvate, hydrate, N-oxide, and/or prodrug thereof. The pulmonary inflammation may be associated with acute lung injury (ALI) and/or acute respiratory distress syndrome (ARDS), which in turn may be associated with viral induced cytokine surge. Such diseases and conditions may be caused by a coronavirus, i.e., severe acute respiratory syndrome coronavirus 2 (SARS- CoV-2), severe acute respiratory syndrome coronavirus (SARS-CoV), or Middle East respiratory syndrome coronavirus (MERS-CoV). This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本发明涉及使用化合物I式或其药用可接受的盐、溶剂化合物、水合物、N-氧化物和/或前药来治疗和预防肺部炎症。肺部炎症可能与急性肺损伤（ALI）和/或急性呼吸窘迫综合征（ARDS）相关联，而这些可能与病毒引起的细胞因子激增有关。这些疾病和状况可能由冠状病毒引起，即严重急性呼吸综合征冠状病毒2（SARS-CoV-2）、严重急性呼吸综合征冠状病毒（SARS-CoV）或中东呼吸综合征冠状病毒（MERS-CoV）引起。本摘要旨在作为特定领域搜索的扫描工具，不限制本发明。