N-methyl-2-hydroxy-5-nitrobenzylamine | 35039-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-methyl-2-hydroxy-5-nitrobenzylamine
• 英文别名: 2-[(Methylamino)methyl]-4-nitrophenol；2-(methylaminomethyl)-4-nitrophenol
• CAS: 35039-53-3
• 化学式: C₈H₁₀N₂O₃
• mdl: MFCD16661450
• 分子量: 182.179
• InChiKey: GBBPFSWFIBWIHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-2-hydroxy-5-nitrobenzylamine 在 镍 氢气 作用下， 以 甲醇 、 异丙醇 为溶剂， 生成 4-amino-2-<(methylamino)methyl>phenol
  参考文献：
  名称：

  N2-1H-Benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines as potential antifilarial agents

  摘要：

  A series of N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI) was synthesized for antifilarial evaluation. Condensation of the requisite beta-keto ester (VI) with N-cyanoguanidine afforded 2-pyrimidinylcyanamides (VIIa,b) and (5,6,7,8-tetrahydro-4-hydroxy-2-quinazolinyl)cyanamide (VIIc). Reaction of VII with a substituted o-phenylenediamine gave 2-(1H-benzimidazol-2-ylamino)-4-pyrimidinols and 2-[(5,6-dichloro-1H-benzimidazol-2-yl)amino]-5,6,7, 8-tetrahydro-4-quinazolinol (IX). Chlorination with phosphoryl chloride, followed by condensation with the appropriate substituted benzenamine, gave the desired N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI). None of these compounds possessed antifilarial activity against Litomosoides carinii or Brugia pahangi infections in jirds.

  DOI：

  10.1021/jm00363a017
• 作为产物：
  描述：

  2-氯甲基-4-硝基苯酚 、 甲胺 以 四氢呋喃 、 水 为溶剂， 反应 0.75h， 以49%的产率得到N-methyl-2-hydroxy-5-nitrobenzylamine
  参考文献：
  名称：

  N2-1H-Benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines as potential antifilarial agents

  摘要：

  A series of N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI) was synthesized for antifilarial evaluation. Condensation of the requisite beta-keto ester (VI) with N-cyanoguanidine afforded 2-pyrimidinylcyanamides (VIIa,b) and (5,6,7,8-tetrahydro-4-hydroxy-2-quinazolinyl)cyanamide (VIIc). Reaction of VII with a substituted o-phenylenediamine gave 2-(1H-benzimidazol-2-ylamino)-4-pyrimidinols and 2-[(5,6-dichloro-1H-benzimidazol-2-yl)amino]-5,6,7, 8-tetrahydro-4-quinazolinol (IX). Chlorination with phosphoryl chloride, followed by condensation with the appropriate substituted benzenamine, gave the desired N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI). None of these compounds possessed antifilarial activity against Litomosoides carinii or Brugia pahangi infections in jirds.

  DOI：

  10.1021/jm00363a017

文献信息

• DERIVATIVES OF STEROID BENZYLAMINES, HAVING AN ANTIPARASITIC ANTIBACTERIAL, ANTIMYCOTIC AND/OR ANTIVIRAL ACTION
  申请人：Becker Katja

  公开号：US20130266645A1

  公开（公告）日：2013-10-10

  The present invention relates to compounds derived from steroids of the general formula (I) wherein L represents a linker and R # represents a steroid residue, the use of compounds of the general formula (I) in medicine and for the prophylaxis and/or the treatment of infectious diseases. Furthermore described are pharmaceutical compositions containing at least one compound of the general formula (I). A further aspect of the invention relates to the synthesis of said compounds of the general formula (I).

  本发明涉及一般式(I)的类固醇衍生物，其中L代表连接剂，R#代表类固醇残基，以及一般式(I)化合物在医学中的使用以及用于传染病的预防和/或治疗。此外，还描述了包含至少一种一般式(I)化合物的药物组合物。本发明的另一个方面涉及一般式(I)化合物的合成。
• Cyclization of Substituted Phenyl N-(2-Hydroxybenzyl)carbamates in Aprotic Solvents. Synthesis of 4H-1,3-Benzoxazin-2(3H)-ones
  作者：Jaromír Mindl、Oldřich Hrabík、Vojeslav Štěrba、Jaromír Kaválek

  DOI：10.1135/cccc20001262

  日期：——

  The kinetics of cyclization of substituted phenyl N-(2-hydroxybenzyl)carbamates and their N-methyl analogs, prepared by the reaction of 2-(aminomethyl)phenols with substituted phenyl chloroformates, was studied in dioxane or toluene at the temperatures 110-180 °C. Electron-withdrawing substituents in the leaving phenoxy group strongly accelerate the rate of cyclization (ρ = 2.45 ± 0.15) while the substituents in the other ring have virtually no effect. The cyclization was catalyzed with triethylamine in toluene but not in dioxane. On the basis of these results, the most convenient method for preparation of substituted 4H-1,3-benzoxazin-2(3H)-ones was a one-hour reflux of substituted 4-nitrophenyl N-(2-hydroxybenzyl)carbamates in dioxane. Based on the influence of substituents, solvents (dioxane and toluene) and triethylamine, the reaction mechanism and structure of the transition state were proposed.

  取代苯基N-(2-羟基苯甲基)氨基甲酸酯及其N-甲基类似物的环化动力学，通过2-(氨基甲基)酚与取代苯基氯甲酸酯反应制备，在二氧六环或甲苯中在110-180°C下进行研究。离去的苯氧基团中的电子吸引取代基强烈加速环化速率（ρ = 2.45 ± 0.15），而另一环中的取代基几乎没有影响。在甲苯中三乙胺催化了环化，但在二氧六环中没有。基于这些结果，制备取代4H-1,3-苯并噁唑-2(3H)-酮的最便捷方法是在二氧六环中将取代4-硝基苯基N-(2-羟基苯甲基)氨基甲酸酯回流一小时。根据取代基、溶剂（二氧六环和甲苯）和三乙胺的影响，提出了反应机理和过渡态的结构。
• Synthesis of Substituted Phenyl N-(2-hydroxybenzyl)-N-Methylcarbamates
  作者：Oldřich Hrabík、Petr Šimůnek、Jaromír Mindl、Jaromír Kaválek

  DOI：10.3390/70200200

  日期：——

  Thirteen previously unreported substituted phenyl N-(2-hydroxybenzyl)-Nmethylcarbamates were prepared by the reaction of substituted 2-hydroxybenzyl-Nmethylamines with phenyl chlorocarbonates. They were identified by their 1H- and 13C-NMR spectra.

  通过取代的 2-羟基苄基甲基胺与苯基氯甲酸酯的反应，制备了 13 种以前未报道过的取代苯基 N-(2-羟基苄基)-甲基氨基甲酸酯。通过 1H 和 13C-NMR 光谱对它们进行了鉴定。
• US9382288B2
  申请人：——

  公开号：US9382288B2

  公开（公告）日：2016-07-05
• [EN] COMPOUNDS BASED ON FOUR AROMATIC RINGS, PREPARATION AND USES THEREOF<br/>[FR] COMPOSES A BASE DE QUATRE CYCLES AROMATIQUES, PREPARATION ET UTILISATIONS
  申请人：CEREP

  公开号：WO2007071840A2

  公开（公告）日：2007-06-28

  [EN] The present invention relates to novel compounds, to the preparation thereof and to uses, in particular therapeutic uses, thereof. It relates more particularly to derived compounds which have at least four aromatic rings, to the preparation thereof and to uses thereof, in particular in the field of human or animal health. These compounds have in particular a certain affinity for neuropeptide Y, NPY, biological receptors, and more particularly for NPY Y1 receptors, present in the central and peripheral nervous systems. The compounds according to the invention are preferably NPY antagonists, and can therefore be used in the therapeutic or prophylactic treatment of any disorder involving NPY. The present invention also relates to pharmaceutical compositions comprising such compounds, to the preparation thereof and to uses thereof, and also to methods of treatment using said compounds.
  [FR] La présente invention concerne de nouveaux composés, leur préparation et leurs utilisations, notamment thérapeutiques. Elle concerne plus particulièrement des composés dérivés présentant au moins quatre cycles aromatiques, leur préparation et leurs utilisations, notamment dans le domaine de la santé humaine ou animale. Ces composés ont en particulier une certaine affinité pour les récepteurs biologiques du neuropeptide Y, NPY et plus particulièrement pour les récepteurs NPY Yl, présents dans les systèmes nerveux central et périphérique. Les composés selon l'invention sont préférentiellement des antagonistes de NPY, et sont donc utilisables dans le traitement thérapeutique ou prophylactique de tout désordre impliquant NPY. La présente invention concerne également des compositions pharmaceutiques comprenant de tels composés, leur préparation et leurs utilisations, ainsi que des méthodes de traitement utilisant lesdits composés.