N-(pyridin-2-ylmethyl)-2-nitroaniline | 126991-23-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(pyridin-2-ylmethyl)-2-nitroaniline
• 英文别名: 2-nitro-N-(pyridin-2-ylmethyl)aniline；N-2-picolyl-o-nitroaniline
• CAS: 126991-23-9
• 化学式: C₁₂H₁₁N₃O₂
• mdl: MFCD09862614
• 分子量: 229.238
• InChiKey: BCJOYUPKFXCHHS-UHFFFAOYSA-N

物化性质

• 沸点：
  393.9±27.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(pyridin-2-ylmethyl)-2-nitroaniline 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 三氯氧磷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 2-chloro-N-picolylbenzimidazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-dihydroimidazo[1,2-a]benzimidazole derivatives against Leishmania donovani and Trypanosoma cruzi

  摘要：

  A high-throughput (HTS) and high-content screening (HCS) campaign of a commercial library identified 2,3-dihydroimidazo[1,2-a]benzimidazole analogues as a novel class of anti-parasitic agents. A series of synthetic derivatives were evaluated for their in vitro anti-leishmanial and anti-trypanosomal activities against Leishmania donovani and Trypanosoma cruzi, which have been known as the causative parasites for visceral leishmaniasis and Chagas disease, respectively. In the case of Leishmania, the compounds were tested in both intracellular amastigote and extracellular promastigote assays. Compounds 4 and 24 showed promising anti-leishmanial activity against intracellular L. donovani (3.05 and 5.29 μM, respectively) and anti-trypanosomal activity against T. cruzi (1.10 and 2.10 μM, respectively) without serious cytotoxicity toward THP-1 and U2OS cell lines.

  DOI：

  10.1016/j.ejmech.2014.07.038
• 作为产物：
  描述：

  2-溴甲基吡啶 、 2-硝基苯胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-(pyridin-2-ylmethyl)-2-nitroaniline
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-dihydroimidazo[1,2-a]benzimidazole derivatives against Leishmania donovani and Trypanosoma cruzi

  摘要：

  A high-throughput (HTS) and high-content screening (HCS) campaign of a commercial library identified 2,3-dihydroimidazo[1,2-a]benzimidazole analogues as a novel class of anti-parasitic agents. A series of synthetic derivatives were evaluated for their in vitro anti-leishmanial and anti-trypanosomal activities against Leishmania donovani and Trypanosoma cruzi, which have been known as the causative parasites for visceral leishmaniasis and Chagas disease, respectively. In the case of Leishmania, the compounds were tested in both intracellular amastigote and extracellular promastigote assays. Compounds 4 and 24 showed promising anti-leishmanial activity against intracellular L. donovani (3.05 and 5.29 μM, respectively) and anti-trypanosomal activity against T. cruzi (1.10 and 2.10 μM, respectively) without serious cytotoxicity toward THP-1 and U2OS cell lines.

  DOI：

  10.1016/j.ejmech.2014.07.038

文献信息

• Substituted pyrido (1,2-c)imidazo(1,2-a)benzimidazoles, processes for
  申请人：Hoechst Aktiengesellschaft

  公开号：US04585775A1

  公开（公告）日：1986-04-29

  The invention relates to compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen, alkyl, trifluoromethyl, halogen, alkoxycarbonyl, alkoxy or alkanoyl, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, methyl, alkoxy or alkoxyethoxy, and R is hydrogen or a group SR.sup.6, in which R.sup.6 is the lone, unpaired electron of the 12-sulfenyl radical, hydrogen, optionally substituted alkyl, alkenyl, alkynyl, alkanoyl, optionally mono- or poly-substituted benzoyl, fuoryl, phenacyl, phenoxyacetyl, phenylacetyl or another conventional thiol-protective group, and to physiologically acceptable salts thereof, and to processes for their preparation, to their use as a gastric acid secretion inhibitor and to pharmaceutical preparations based on these compounds.

  本发明涉及公式## STR1 ##的化合物，其中R.sup.1和R.sup.2相同或不同，可以是氢、烷基、三氟甲基、卤素、烷氧羰基、烷氧基或烷酰基，R.sup.3、R.sup.4和R.sup.5相同或不同，可以是氢、甲基、烷氧基或烷氧乙氧基，而R是氢或SR.sup.6基团，其中R.sup.6是12-硫醇基团的孤立未成对电子，可以是氢、可选取代的烷基、烯基、炔基、烷酰基、可选取代的单或多取代苯甲酰基、氟苯基、苯乙酰基、苯氧乙酰基、苯乙酸基或其他常规硫醇保护基团，以及其生理上可接受的盐，并且涉及制备这些化合物的过程，以及它们作为胃酸分泌抑制剂的用途和基于这些化合物的制药制剂。
• Pendent supported rare coordination for flavin: Structural, photophysical and morphological characterization of flavin-silver(I) complexes
  作者：M.S.S. Vinod Mouli、Ashutosh Kumar Mishra

  DOI：10.1016/j.ica.2023.121752

  日期：2023.12

  stabilizing the rare bidentate coordinate mode for the flavin entity, via pendent supported secondary coordination; thereby resulting in a polymeric structure. Subtle chemical modification around the flavin core structure incorporating allyl and picolyl functionality in proximity to the secondary coordinate site was envisaged and two novel flavin analogues allylflavin (AF) and picolylflavin (PiF) was

  本手稿讨论了我们通过悬垂支持的二级配位来稳定黄素实体罕见的双齿配位模式的努力；从而产生聚合结构。设想围绕黄素核心结构进行微妙的化学修饰，在二级配位位点附近结合烯丙基和吡啶甲基官能团，并设想两种新型黄素类似物烯丙基黄素 ( AF ) 和吡啶甲基黄素 ( PiF )）被合成并进行固态X射线衍射研究以阐明其银配合物的结构特征。有趣的是，发现两个晶体学上独特的银离子是特征，根据银离子在黄素单元的初级或次级位点的配位情况，观察到银离子周围有不同的几何形状。此外，通过光物理技术探讨了络合行为，并进行了形态学研究以确定配位聚合物基序轻松转移到表面上。
• Imidazoquinoxaline compounds and their preparation and use
  申请人：NOVO NORDISK A/S

  公开号：EP0344943A1

  公开（公告）日：1989-12-06

  New imidazoquinoxaline compounds having the general formula wherein R³ is or CO₂R′ wherein R′ is C₃₋₇-cycloalkyl; R⁵ is methyl, which is substituted with hydrogen, alkoxycar­bonyl, heteroaryl, morpholino C₃₋₇-cycloalkyl, C₁₋₆-alkenyl, arylacyl, alkylacyl, alkoxyalkyl, alkoxy, phthalimidophenyl, aralkyl or aryl, all of which are substituted with hydrogen, halogen, C₁₋₆-alkyl, amino, azido, of C₁₋₆-alkoxy; and R₆ is H, C₁₋₆-alkyl, halogen, or CF₃. The compounds are useful in psychopharmaceutical preparati­ons as anticonvulsants, anxiolytics, hypnotics, and in improving the cognitive function of the brain of mammals.

  通式如下的新咪唑喹喔啉化合物 其中 R³ 是 或 CO₂R′ 其中 R′是 C₃₋₇-环烷基； R⁵ 是甲基，它被氢、烷氧羰基、杂芳基、吗啉基 C₃₋₇-环烷基、C₁₋₆-烯基、芳基酰基、烷基酰基取代、烷氧基烷基、烷氧基、邻苯二甲酰亚胺基苯基、芳基或芳基，所有这些都被氢、卤素、C₁₋₆-烷基、氨基、叠氮、C₁₋₆-烷氧基取代； R₆ 是 H、C₁₋₆-烷基、卤素或 CF₃。 这些化合物可作为抗惊厥药、抗焦虑药、催眠药和改善哺乳动物大脑认知功能的精神药物制剂。
• Translocator protein ligands based on N -methyl-(quinolin-4-yl)oxypropanamides with properties suitable for PET radioligand development
  作者：Chad Brouwer、Kimberly J. Jenko、Sami S. Zoghbi、Cheryl L. Morse、Robert B. Innis、Victor W. Pike

  DOI：10.1016/j.ejmech.2016.08.046

  日期：2016.11

  Modifications to an N-methyl-(quinolin-4-yl)oxypropanamide scaffold were explored to discover leads for developing new radioligands for PET imaging of brain TSPO (translocator protein), a biomarker of neuroinfiammation. Whereas contraction of the quinolinyl portion of the scaffold or cyclization of the tertiary amido group abolished high TSPO affinity, insertion of an extra nitrogen atom into the 2-arylquinolinyl portion was effective in retaining sub-nanomolar affinity for rat TSPO, while also decreasing lipophilicity to within the moderate range deemed preferable for a PET radioligand. Replacement of a phenyl group on the amido nitrogen with an isopropyl group was similarly effective. Among others, compound 20 (N-methyl-N-phenyl-2-[2-(pyridin-2-yl)-1,8-naphthyridin-4-yloxy]propanamide) appears especially appealing for PET radioligand development, based on high selectivity and high affinity (K-i = 0.5 nM) for rat TSPO, moderate lipophilicity (logD = 2.48), and demonstrated amenability to labeling with carbon-11. Published by Elsevier Masson SAS.
• Substituierte Pyrido(1,2-c)imidazo((1,2-a)benzimidazole, Verfahren zu ihrer Herstellung, ihre Verwendung sowie pharmazeutische Präparate auf Basis dieser Verbindungen
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0138034B1

  公开（公告）日：1989-03-29