3-(phenylamino)quinoxalin-2(1H)-one | 1770-48-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(phenylamino)quinoxalin-2(1H)-one
• 英文别名: 2-Phenylaminochinoxalinon；3-anilino-1H-quinoxalin-2-one；3-(Phenylamino)quinoxalin-2-ol；3-anilino-1H-quinoxalin-2-one
• CAS: 1770-48-5
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: PBDYBTRQKOMYFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(phenylamino)quinoxalin-2(1H)-one 在 溶剂黄146 、 三乙胺 作用下， 以 二恶烷 、 乙醇 为溶剂， 反应 0.03h， 生成 3-choro-4-(furan-3-yl)-1-(2-((E)-((E)-3-(phenylimino)-3,4-dihydroquinoxalin-2-(1H)-ylidene)amino)phenyl)azetidin-2-one
  参考文献：
  名称：

  Synthesis, In Vitro Antitubercular Activity and 3D-QSAR of Novel Quinoxaline Derivatives

  摘要：

  Twenty new quinoxalines bearing azetidinone and thiazolidinone groups were synthesized by cyclocondensation of Schiff bases of quinoxaline‐2, 3‐dione and were characterized with several analytical tools. They were tested against Mycobacterium tuberculosis H37Rv at a concentration of 10 μg/mL by Microplate Alamar Blue Assay method. Quinoxaline derivatives with 2‐chloro, dimethylamino and nitro substitutions exhibited in vitro activity, comparable to that of the drug, isoniazid. Three‐dimensional quantitative structure–activity relationship studies indicated that electrostatic and steric field descriptors could explain the observed activity. The developed model fits the data well and has good predictive capability (r2 = 0.81, q2 = 0.71, F = 27.06, r2_pred = 0.84, r2 m = 0.84, r2 BS = 0.80). Electronegative groups play an important role in the antitubercular activity.

  DOI：

  10.1111/j.1747-0285.2011.01246.x
• 作为产物：
  描述：

  3-Phenoxyquinoxalin-2-amine 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 1.5h， 以53%的产率得到3-(phenylamino)quinoxalin-2(1H)-one
  参考文献：
  名称：

  通过微波介导的Smiles重排新颖合成3-苯胺基-吡嗪-2（1 H）-和3-苯胺基-喹喔啉-2-（1 H）-

  摘要：

  在这封信中，我们报告了一种从相应的3-卤代吡嗪-2-制备3-苯胺基-吡嗪-2（1 H）-和3-苯胺基-喹喔啉-2（1 H）-的新颖方法。胺和3-卤代喹喔啉-2-胺，使用微波介导的Smiles重排。

  DOI：

  10.1016/j.tetlet.2008.01.056

文献信息

• [EN] AZETIDINE-SUBSTITUTED QUINOXALINE-TYPE PIPERIDINE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE PIPÉRIDINE DE TYPE QUINOXALINE SUBSTITUÉE PAR UNE AZÉTIDINE ET LEURS UTILISATIONS
  申请人：PURDUE PHARMA LP

  公开号：WO2013080036A1

  公开（公告）日：2013-06-06

  The disclosure relates to Azetidine-Substituted Quinoxaline-Type Piperidine Compounds of Formula (I): and pharmaceutically acceptable derivatives thereof wherein the R1, R2, R3, Q, Y1, Z, A, B, a, and b are as defined herein, compositions comprising an effective amount of an Azetidine-Substituted Quinoxaline-Type Piperidine Compound, and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of an Azetidine-Substituted Quinoxaline-Type Piperidine Compound.

  该披露涉及公式(I)的氮杂环丙烷取代喹喔啉型哌啶化合物及其药用可接受的衍生物，其中R1、R2、R3、Q、Y1、Z、A、B、a和b如本文所定义，包含有效量氮杂环丙烷取代喹喔啉型哌啶化合物的组合物，以及治疗或预防疾病（如疼痛）的方法，包括向需要的动物施用有效量氮杂环丙烷取代喹喔啉型哌啶化合物。
• New α-Amido-α-aminonitrones As Building Blocks for Constructing ­Heterocyclic Systems
  作者：Bartosz Trzewik、Dariusz Cież、Maciej Hodorowicz、Katarzyna Stadnicka

  DOI：10.1055/s-2008-1067236

  日期：2008.9

  New, stable α-amido-α-aminonitrones were obtained in good yields from 3-oxobutyric acid N-pyridin-2-ylamides and nitrosobenzene. The α-amido-α-aminonitrones were then used as new, versatile building blocks to obtaining various heterocycles with both bielectrophilic and binucleophilic reagents. With diiodomethane as reagent, 1,2,5-oxadiazine derivatives were formed, whereas reactions with aromatic 1,2-, 1,3- and 1,4-diamines yielded quinoxaline, quinazoline, perimidine, and dibenzo[d,f][1,3]diazepine derivatives, respectively.

  新、稳定的α-酰胺-α-氨基亚硝胺以良好的产率从3-氧代丁酸N-吡啶-2-基酰胺和亚硝基苯获得。然后，α-酰胺-α-氨基亚硝胺被用作新的、多功能的构建块，利用双电亲和体和双核亲和体试剂获得各种杂环化合物。使用二碘甲烷作为试剂，形成了1,2,5-噁二嗪衍生物，而与芳香性1,2、1,3和1,4-二胺的反应分别产生了喹喔啉、喹唑啉、苯并咪唑和二苯并[d,f][1,3]二氮杂萘衍生物。
• Synthesis, Leptospirocidal Activity and QSAR Analysis of Novel Quinoxaline Derivatives
  作者：Ayarivan Puratchikody、Ramalakshmi Natarajan、Mukesh Doble、Shanmugam Hema Iswarya、Raj Vijayabharathi

  DOI：10.2174/1573406411309020010

  日期：2013.1.1

  A simple and efficient method has been developed for the synthesis of series of N-Mannich bases of (E)-3- (phenylimino/4-chlorophenylimino)-2,3-dihydro-1-[(N-substituted piperazinyl) methyl]quinoxaline-2-(1H)-one 3a-f and 4a-f. The requisite 2a and 2b were obtained by reaction between quinoxaline-2,3-dione 1 and aniline/p-chloroaniline. These compounds underwent NMannich reaction with various substituted

  已开发出一种简单有效的方法来合成（E）-3-（苯基亚氨基/ 4-氯苯基亚氨基）-2,3-二氢-1-[（N-取代的哌嗪基）甲基]的一系列N-曼尼希碱喹喔啉-2-（1H）-1 3a-f和4a-f。通过喹喔啉-2，3-二酮1与苯胺/对氯苯胺之间的反应获得所需的2a和2b。这些化合物与各种取代的哌嗪进行NMannich反应生成（分别为标题化合物3a-f和4a-f。通过光谱研究（IR，1H NMR，13C NMR和质量）和元素分析确认合成的化合物的结构。筛选这些化合物对问号钩端螺旋体的体外杀钩虫活性，对在体外研究中表现出最大活性的有效化合物4a，4b和4c进行体内研究。确定了羧肽酶和转肽酶对钩端螺旋体病的抑制活性。开发的3D-QSAR研究模型表明，需要更多的疏水性和更少的空间基团作为取代基，以增强体外活性。
• Synthesis, Characterization and Antimicrobial Activity of 1,2-dihydroquinoxaline-3-yl-3-Substitutedphenyl-1<i>H</i>-pyrazole-4-Carbaldehyde
  作者：Visagaperumal Dhanapal、Jayakumar Ramalingam、Anbalagan Navaneetha Raman

  DOI：10.1002/jhet.2663

  日期：2017.3

  A series of 1,2‐dihydroquinoxaline‐3‐yl‐3‐substitutedphenyl‐1H‐pyrazole‐4‐carbaldehyde were synthesized and evaluated for their antimicrobial activity against two Gram‐positive and two Gram‐negative organisms and two fungal organisms. The study has shown that pyrazole‐4‐carbaldehyde‐incorporated quinoxaline was essential for activity. Among the compounds, 5a, 5c, 5d had shown significant activity against

  合成了一系列1,2-二氢喹喔啉-3-基-3-取代苯基-1 H-吡唑-4-甲醛，并评估了它们对两种革兰氏阳性和两种革兰氏阴性生物和两种真菌生物的抗菌活性。研究表明，吡唑-4-甲醛与喹喔啉的结合对于活性至关重要。在这些化合物中，与对照相比，5a，5c，5d对所有选定的菌株均表现出显着的活性。这些化合物可能被证明可用作抗菌剂。
• QUINAZOLIN-4(3H)-ONE-TYPE PIPERIDINE COMPOUNDS AND USES THEREOF
  申请人：TADESSE Dawit

  公开号：US20160002203A1

  公开（公告）日：2016-01-07

  The present disclosure relates to Quinazolin-4(3H)-one-Type Piperidine Compounds, such as those of Formula (I) and the pharmaceutically acceptable salts and solvates thereof, wherein R 1 , R 2 , R 3 , Q, Y 1 , Z, A, B, E, and a are as defined herein; compositions comprising an effective amount of a Quinazolin-4(3H)-one-Type Piperidine Compound, and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of a Quinazolin-4(3H)-one-Type Piperidine Compound.

  本公开涉及喹唑啉-4(3H)-酮型哌啶化合物，例如公式（I）中的化合物及其药学上可接受的盐和溶剂化物，其中R1、R2、R3、Q、Y1、Z、A、B、E和a的定义如本文所述；包含有效量喹唑啉-4(3H)-酮型哌啶化合物的组合物；以及通过向需要治疗或预防疾病，例如疼痛的动物施用有效量喹唑啉-4(3H)-酮型哌啶化合物的方法。