A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives

被引:0
|
作者
Muhammad Shoaib Ali Gill
Nursyuhada Azzman
Sharifah Syed Hassan
Syed Adnan Ali Shah
Nafees Ahemad
机构
[1] Monash University Malaysia,School of Pharmacy
[2] Monash University Malaysia,Jeffrey Cheah School of Medicine and Health Sciences
[3] University of Veterinary and Animal Sciences,Institute of Pharmaceutical Sciences
[4] Syed Abdul Qadir Jillani,Faculty of Pharmacy
[5] Universiti Teknologi MARA,Faculty of Pharmacy
[6] Universiti Teknologi MARA Cawangan Selangor Kampus Puncak Alam,Tropical Medicine and Biology Multidisciplinary Platform
[7] Monash University Malaysia,undefined
来源
BMC Chemistry | / 16卷
关键词
Green synthesis; 4-Quinolone; N-Alkylation; Carboxamide; Scalable;
D O I
暂无
中图分类号
学科分类号
摘要
Quinolone is a privileged scaffold in medicinal chemistry and 4-Quinolone-3-Carboxamides have been reported to harbor vast therapeutic potential. However, conversion of N-1 substituted 4-Quinolone 3-Carboxylate to its corresponding carbamates is highly restrictive. This motivated us to adopt a much simpler, scalable and efficient methodology for the synthesis of highly pure N-1 substituted 4- Quinolone-3-Carboxamides with excellent yields. Our adopted methodology not only provides a robust pathway for the convenient synthesis of N-1 substituted 4- Quinolone-3-Carboxamides which can then be explored for their therapeutic potential, this may also be adaptable for the derivatization of other such less reactive carboxylate species.
引用
收藏
相关论文
共 50 条
  • [21] Synthesis of 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide and 3-oxo-3, 4-dihydrobenzo[b][1,4]oxazine-8-carboxamide derivatives as PARP1 inhibitors
    Shao, Xuwei
    Pak, Steven
    Velagapudi, Uday Kiran
    Gobbooru, Shruthi
    Kommaraju, Sai Shilpa
    Low, Woon-Kai
    Subramaniam, Gopal
    Pathak, Sanjai Kumar
    Talele, Tanaji T.
    BIOORGANIC CHEMISTRY, 2020, 102
  • [22] Discovery of N-(2,4-Di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (VX-770, Ivacaftor), a Potent and Orally Bioavailable CFTR Potentiator
    Hadida, Sabine
    Van Goor, Fredrick
    Zhou, Jinglan
    Arumugam, Vijayalaksmi
    McCartney, Jason
    Hazlewood, Anna
    Decker, Caroline
    Negulescu, Paul
    Grootenhuis, Peter D. J.
    JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (23) : 9776 - 9795
  • [23] A NEW AND PRACTICAL SYNTHESIS OF 7-(3-CHLOROPROPOXY)-6-METHOXY-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBONITRILE
    Mao, Yongjun
    Qin, Jianfeng
    He, Haijun
    Liu, Gang
    Gao, Bingyi
    Wang, Han
    HETEROCYCLES, 2014, 89 (08) : 1885 - 1891
  • [24] Regioselective nucleophilic substitution of halogen derivatives of 1-substituted 4-oxo-1,4-dihydroquinoline-3-carboxylic acids
    Hermecz, I
    Vasvari-Debreczy, L
    Podanyi, B
    Kereszturi, G
    Balogh, M
    Horvath, A
    Varkonyi, P
    HETEROCYCLES, 1998, 48 (06) : 1111 - 1116
  • [25] Design, synthesis and pharmacological evaluation of 1,3,6-trisubstituted-4-oxo-1,4-dihydroquinoline-2-carboxylic acid derivatives as selective ETA antagonists
    Khadtare, Nikhil
    Stephani, Ralph
    Korlipara, Vijaya
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [26] 1-ethyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
    Lou, Benyong
    Bostrom, Dan
    Velaga, Sitaram P.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O4281 - U3023
  • [27] 1-Cyclopropyl-6-fluoro-7-(4-nitrosopiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
    Li, Tao
    Tang, Li-Rong
    Zeng, Qiao-Ling
    Chen, Wei-Jin
    Huang, Biao
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2053 - U4652
  • [28] 1-Cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
    Li, XW
    Zhi, F
    Shen, JH
    Hu, YQ
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O2235 - O2236
  • [29] A Practical Synthesis of 7-(3-Chloropropoxy)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile, a Key Intermediate to Bosutinib
    Mao, Yongjun
    Tian, Xin
    Jiang, Luobin
    Zhu, Guoqing
    Wang, Han
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2015, 47 (03) : 207 - 213
  • [30] 1-ethyl-6-fluoro-7-(4-methylpiperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate hexahydrate
    An, Zhe
    Liang, Qing-Cheng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O441 - U2316