Three-Step Synthesis of N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide from 4,7-Dichloroquinoline

被引:0
|
作者
Acevedo, Deiby F. Aparicio [1 ]
Villamizar, Marlyn C. Ortiz [1 ]
Kouznetsov, Vladimir V. [1 ]
机构
[1] Univ Ind Santander, Escuela Quim, Lab Quim Organ & Biomol, Cl 9 Cra 27, Bucaramanga 680006, Colombia
关键词
4,7-dichloroquinoline; N-oxides; C-H bond functionalization; C2-amide formation reaction; C4 SNAr reaction; N-(quinolinyl)morpholines; N-(quinolinyl)amides; Lipinski's descriptors; QUINOLINE N-OXIDES; DESIGN; IDENTIFICATION; FUNCTIONALIZATION; CHEMISTRY;
D O I
10.3390/M1796
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The quinoline derivative, N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide, was synthesized in a conventional three-step procedure from 4,7-dichloroquinoline using a N-oxidation reaction/C2-amide formation reaction/C4 SNAr reaction sequence. The structure of the compound was fully characterized by FT-IR, 1H-, C-13-NMR, DEPT-135(degrees), and ESI-MS techniques. Its physicochemical parameters (Lipinski's descriptors) were also calculated using the online SwissADME database. Such derivatives are relevant therapeutic agents exhibiting potent anticancer, antibacterial, antifungal, and antiparasitic properties.
引用
收藏
页数:8
相关论文
共 50 条
  • [31] Crystal structure of 4-chloro-N-[2-(piperidin-1-yl)ethyl]benzamide monohydrate
    Prathebha, K.
    Jonathan, D. Reuben
    Revathi, B. K.
    Sathya, S.
    Usha, G.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O39 - +
  • [32] N-[7-Chloro-4-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl]quinoline]-acetamide
    Coghi, Paolo
    Ng, Jerome P. L.
    Nasim, Ali Adnan
    Wong, Vincent Kam Wai
    MOLBANK, 2021, 2021 (02)
  • [33] A Three-Step Synthesis of 4H-Cyclopenta[def]phenanthrene from Pyrene
    van der Ham, Alex
    Overkleeft, Hermen S.
    Filippov, Dmitri V.
    Schneider, Gregory F.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (13) : 2013 - 2017
  • [34] Synthesis, Cytotoxic Evaluation, and Molecular Docking Studies of N-(7-hydroxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetamide/benzamide Analogues
    Ahsan, Mohamed Jawed
    Kumawat, Rupesh Kumar
    Jadav, Surender Singh
    Geesi, Mohammed H.
    Bakht, Mohammed Afroz
    Hassan, Mohd Zaheen
    Al-Tamimis, Abdulmalik Bin Saleh
    Riadi, Yassine
    Salahuddin
    Hussain, Afzal
    Ganta, Narayana Murthy
    Khalilullah, Habibullah
    LETTERS IN DRUG DESIGN & DISCOVERY, 2019, 16 (02) : 182 - 193
  • [35] N-(4-(quinazolin-2-yl)phenyl)benzamide derivatives with potent anti-angiogenesis activities: synthesis and evaluation
    Ming Sun
    Na Lv
    Zeng Li
    Qiru Xiong
    Liang Xu
    Zongsheng Yin
    Journal of the Iranian Chemical Society, 2016, 13 : 753 - 761
  • [36] N-{3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoyl}-N′-(4,6-dimethylpyrimidin-2-yl)thiourea
    Peng, Hao
    He, Hong-Wu
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2006, 62 : O5371 - O5372
  • [37] N-(4-Methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide
    Korlyukov, Alexander A.
    Dorovatovskii, Pavel V.
    Vologzhanina, Anna V.
    MOLBANK, 2022, 2022 (04)
  • [38] N-(4-(quinazolin-2-yl)phenyl)benzamide derivatives with potent anti-angiogenesis activities: synthesis and evaluation
    Sun, Ming
    Lv, Na
    Li, Zeng
    Xiong, Qiru
    Xu, Liang
    Yin, Zongsheng
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2016, 13 (04) : 753 - 761
  • [39] A New and Improved Process for N-(4-Chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide
    Mao, Yongjun
    Liu, Zheng
    Yang, Xiaojun
    Xia, Xiangfei
    Zhang, Rongxia
    Li, Jianfeng
    Jiang, Xiangrui
    Xie, Kai
    Zheng, Jin
    Zhang, Hui
    Suo, Jin
    Shen, Jingshan
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (12) : 1970 - 1973
  • [40] N-(1,10-phenanthrolin-5-yl)-4-(2-pyridyl)benzamide monohydrate
    Kobayashi, Masayuki
    Masaoka, Shigeyuki
    Sakai, Ken
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1979 - U4257