5-硝基-2-哌啶苯胺 | 5367-58-8

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 5-硝基-2-哌啶苯胺
• 中文别名: 5-硝基-2-哌啶子基苯胺
• 英文名称: 5-nitro-2-(piperidin-1-yl)aniline
• 英文别名: 5-Nitro-2-piperidino-anilin；5-nitro-2-piperidinoaniline；5-nitro-2-piperidin-1-ylaniline
• CAS: 5367-58-8
• 化学式: C₁₁H₁₅N₃O₂
• mdl: MFCD00852821
• 分子量: 221.259
• InChiKey: DMIMWGHYIPFAIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光，并保存在惰性气体环境中。

反应信息

• 作为反应物：
  描述：

  5-硝基-2-哌啶苯胺 在 碘苯 、 Selectfluor 、 三氟乙酸 作用下， 以76 %的产率得到7-nitro-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyridine
  参考文献：
  名称：

  碘(III)催化芳基胺氧化环化构建N-烷基苯并咪唑

  摘要：

  开发了一种使用 selectflu 作为氧化剂的 I(III) 催化氧化环化反应，将邻位取代的苯胺转化为苯并咪唑。该反应温和，仅需要0.5 mol%的碘苯，且其范围很广：苯胺部分上的吸电子或释放电子基团是可以接受的，并且允许环状或无环N-烷基胺作为邻位取代基。初步机理研究表明，苯并咪唑的形成是通过阳离子反应中间体发生的，并且测量到了 1.98 ± 0.05 的分子内动力学同位素效应。

  DOI：

  10.1021/acs.joc.4c00346
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 tin(ll) chloride 作用下， 生成 5-硝基-2-哌啶苯胺
  参考文献：
  名称：

  Spiegel; Kaufmann, Chemische Berichte, 1908, vol. 41, p. 682

  摘要：

  DOI：

文献信息

• [EN] SMALL MOLECULE AGONISTS OF MUCOLIPIN 1 AND USES THEREOF<br/>[FR] PETITES MOLÉCULES AGONISTES DE LA MUCOLIPINE 1 ET LEURS UTILISATIONS
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2021041866A1

  公开（公告）日：2021-03-04

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a phenyl-sulfonic amide (or similar) structure which function as agonists of mucolipin 1 (ML1), and their use as therapeutics for the treatment of Duchenne muscular dystrophy (DMD) and related disorders.

  这项发明属于药物化学领域。特别是，该发明涉及一类新的小分子，具有苯磺酰胺（或类似）结构，作为肌球脂蛋白1（ML1）的激动剂，以及它们作为治疗杜氏肌肉萎缩症（DMD）和相关疾病的疗法的用途。
• Synthesis of quinoxaline derivatives from substituted acetanilides through intramolecular quaternization reactions
  作者：Sonia de Castro、Roberto Chicharro、Vicente J. Arán

  DOI：10.1039/b109725c

  日期：2002.3.8

  The cyclization of 2-dialkylamino-2′-halogeno- and 2-chloro-2′-(dialkylamino)acetanilides to quinoxaline derivatives has been studied in detail. These reactions proceed, respectively, through intramolecular aromatic nucleophilic or aliphatic nucleophilic substitution reactions and depending on the substituents and the experimental conditions, they lead to 3-oxoquinoxalinium salts or, after an alkyl chloride elimination, to quinoxalin-2-ones. Some new cases of the little known intramolecular quaternization of tertiary amines with aryl halides are described.

  对2-二烷基氨基-2′-卤烷基和2-氯-2′-(二烷基氨基)乙酰苯胺环化为喹喏啉衍生物的反应进行了详细研究。根据取代基和实验条件，这些反应通过分子内芳香族亲核或脂肪族亲核取代反应进行，分别生成3-氧喹喏啉盐，或者在消除烷基氯之后生成喹喏啉-2-酮。还描述了一些关于芳基卤化物与三氟氨基化物的分子内季铵化的新案例。
• Sodium dithionite in the regioselective reduction of the ortho-positioned nitro group in 1-R-2,4-dinitrobenzenes
  作者：Michael D. Tsymliakov、Anita I. Maksutova、Elena N. Bezsonova、Daria V. Zakharova、Yuri K. Grishin、Victor A. Tafeenko、Sergey E. Sosonyuk、Natalia A. Lozinskaya

  DOI：10.1016/j.mencom.2023.01.038

  日期：2023.1

  1-R-2,4-Dinitrobenzenes are regioselectively reduced with sodium dithionite at near-neutral pH into the product having amino group ortho to the substituent R. Although the yields of products varied from moderate to good, the procedure does not involve the use of transition metals.

  1-R-2,4-二硝基苯在接近中性的 pH 条件下被连二亚硫酸钠区域选择性还原成具有取代基 R邻位氨基的产物。虽然产物的产率从中等到良好不等，但该过程不涉及使用过渡金属。
• Antiprotozoan lead discovery by aligning dry and wet screening: Prediction, synthesis, and biological assay of novel quinoxalinones
  作者：Miriam A. Martins Alho、Yovani Marrero-Ponce、Stephen J. Barigye、Alfredo Meneses-Marcel、Yanetsy Machado Tugores、Alina Montero-Torres、Alicia Gómez-Barrio、Juan J. Nogal、Rory N. García-Sánchez、María Celeste Vega、Miriam Rolón、Antonio R. Martínez-Fernández、José A. Escario、Facundo Pérez-Giménez、Ramón Garcia-Domenech、Norma Rivera、Ricardo Mondragón、Mónica Mondragón、Froylán Ibarra-Velarde、Atteneri Lopez-Arencibia、Carmen Martín-Navarro、Jacob Lorenzo-Morales、Maria Gabriela Cabrera-Serra、Jose Piñero、Jan Tytgat、Roberto Chicharro、Vicente J. Arán

  DOI：10.1016/j.bmc.2014.01.036

  日期：2014.3

  Protozoan parasites have been one of the most significant public health problems for centuries and several human infections caused by them have massive global impact. Most of the current drugs used to treat these illnesses have been used for decades and have many limitations such as the emergence of drug resistance, severe side-effects, low-to-medium drug efficacy, administration routes, cost, etc. These drugs have been largely neglected as models for drug development because they are majorly used in countries with limited resources and as a consequence with scarce marketing possibilities. Nowadays, there is a pressing need to identify and develop new drug-based antiprotozoan therapies. In an effort to overcome this problem, the main purpose of this study is to develop a QSARs-based ensemble classifier for antiprotozoan drug-like entities from a heterogeneous compounds collection. Here, we use some of the TOMO-COMD-CARDD molecular descriptors and linear discriminant analysis (LDA) to derive individual linear classification functions in order to discriminate between antiprotozoan and non-antiprotozoan compounds as a way to enable the computational screening of virtual combinatorial datasets and/or drugs already approved. Firstly, we construct a wide-spectrum benchmark database comprising of 680 organic chemicals with great structural variability (254 of them antiprotozoan agents and 426 to drugs having other clinical uses). This series of compounds was processed by a k-means cluster analysis in order to design training and predicting sets. In total, seven discriminant functions were obtained, by using the whole set of atom-based linear indices. All the LDA-based QSAR models show accuracies above 85% in the training set and values of Matthews correlation coefficients (C) vary from 0.70 to 0.86. The external validation set shows rather-good global classifications of around 80% (92.05% for best equation). Later, we developed a multi-agent QSAR classification system, in which the individual QSAR outputs are the inputs of the aforementioned fusion approach. Finally, the fusion model was used for the identification of a novel generation of lead-like antiprotozoan compounds by using ligand-based virtual screening of 'available' small molecules (with synthetic feasibility) in our 'in-house' library. A new molecular subsystem (quinoxalinones) was then theoretically selected as a promising lead series, and its derivatives subsequently synthesized, structurally characterized, and experimentally assayed by using in vitro screening that took into consideration a battery of five parasite-based assays. The chemicals 11(12) and 16 are the most active (hits) against apicomplexa (sporozoa) and mastigophora (flagellata) subphylum parasites, respectively. Both compounds depicted good activity in every protozoan in vitro panel and they did not show unspecific cytotoxicity on the host cells. The described technical framework seems to be a promising QSAR-classifier tool for the molecular discovery and development of novel classes of broad-antiprotozoan-spectrum drugs, which may meet the dual challenges posed by drug-resistant parasites and the rapid progression of protozoan illnesses. (C) 2014 Elsevier Ltd. All rights reserved.
• Syntheses in the pyrido- and piperido-(1′ : 2′-1 : 2)benziminazole series
  作者：K. H. Saunders

  DOI：10.1039/jr9550003275

  日期：——