Synthesis and Anticancer Evaluation of Novel 7-Aza-Coumarine-3-Carboxamides

被引:5
|
作者
Trifonov, Alexey V. [1 ]
Gazizov, Almir S. [1 ]
Tapalova, Anipa S. [2 ]
Kibardina, Lyudmila K. [1 ]
Appazov, Nurbol O. [2 ]
Voloshina, Alexandra D. [1 ]
Sapunova, Anastasiia S. [1 ]
Luybina, Anna P. [1 ]
Abyzbekova, Gulmira M. [2 ]
Dobrynin, Alexey B. [1 ]
Litvinov, Igor A. [1 ]
Tauekel, Akerke K. [3 ]
Yespenbetova, Sholpan O. [2 ]
Burilov, Alexander R. [1 ]
Pudovik, Michail A. [1 ]
机构
[1] Russian Acad Sci, Arbuzov Inst Organ & Phys Chem, FRC Kazan Sci Ctr, Arbuzova Str 8, Kazan 420088, Russia
[2] Korkyt Ata Kyzylorda Univ, Aiteke Bi St 29A, Kyzylorda 120014, Kazakhstan
[3] Kazan Natl Res Technol Univ, Dept Oil Chem & Nanotechnol, Karl Marx Str 68, Kazan 420015, Russia
基金
俄罗斯科学基金会;
关键词
aza-coumarine; amides; cytotoxicity; selectivity; anti-tumor; OPTICAL-PROPERTIES; SCAFFOLD; DERIVATIVES; COUMARINS; AGENTS;
D O I
10.3390/ijms24129927
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Herein, we report the design and synthesis of novel 7-aza-coumarine-3-carboxamides via scaffold-hopping strategy and evaluation of their in vitro anticancer activity. Additionally, the improved non-catalytic synthesis of 7-azacoumarin-3-carboxylic acid is reported, which features water as the reaction medium and provides a convenient alternative to the known methods. The anticancer activity of the most potent 7-aza-coumarine-3-carboxamides against the HuTu 80 cell line is equal to that of reference Doxorubicin, while the selectivity towards the normal cell line is 9-14 fold higher.
引用
收藏
页数:19
相关论文
共 50 条
  • [1] Novel quinoline-3-carboxamides (Part 2): Design, optimization and synthesis of quinoline based scaffold as EGFR inhibitors with potent anticancer activity
    Aly, Rasha M.
    Serya, Rabah A. T.
    El-Motwally, Amira M.
    Esmat, Ahmed
    Abbas, Safinaz
    Abou El Ella, Dalal A.
    BIOORGANIC CHEMISTRY, 2017, 75 : 368 - 392
  • [2] Design, synthesis and biological evaluation of novel α-acyloxy carboxamides via Passerini reaction as caspase 3/7 activators
    Ayoup, Mohammed Salah
    Wahby, Yasmin
    Abdel-Hamid, Hamida
    Ramadan, El Sayed
    Teleb, Mohamed
    Abu-Serie, Marwa M.
    Noby, Ahmed
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 168 : 340 - 356
  • [3] Synthesis and in vitro anticancer activity of some novel cyclohepta[b]thiophene-3-carboxamides bearing pyrazole moiety
    Al-Ghorbani, Mohammed
    Gouda, Moustafa A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (08) : 3213 - 3221
  • [4] Design, synthesis and in vitro anticancer evaluation of 4,6-diamino-1,3,5-triazine-2-carbohydrazides and -carboxamides
    Kothayer, Hend
    Elshanawani, Abdalla A.
    Abu Kull, Mansour E.
    El-Sabbagh, Osama I.
    Shekhar, Malathy P. V.
    Brancale, Andrea
    Jones, Arwyn T.
    Westwell, Andrew D.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (24) : 6886 - 6889
  • [5] 2-(3′-Indolyl)-N-arylthiazole-4-carboxamides: Synthesis and evaluation of antibacterial and anticancer activities
    Tantak, Mukund P.
    Wang, Jing
    Singh, Rajnish Prakash
    Kumar, Anil
    Shah, Kavita
    Kumar, Dalip
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (19) : 4225 - 4231
  • [6] Synthesis and biological evaluation of chromone-3-carboxamides
    Gordon, Allen T.
    Ramaite, Isaiah D. I.
    Mnyakeni-Moleele, Simon S.
    ARKIVOC, 2020, : 148 - 160
  • [7] Synthesis, DNA Interactions and Anticancer Evaluation of Novel Diamidine Derivatives of 3,4-Ethylenedioxythiophene
    Stolic, Ivana
    Avdicevic, Monika
    Bregovic, Nikola
    Piantanida, Ivo
    Glavas-Obrovac, Ljubica
    Bajic, Miroslav
    CROATICA CHEMICA ACTA, 2012, 85 (04) : 457 - 467
  • [8] Synthesis and biological evaluation of novel bavachinin analogs as anticancer agents
    Gupta, Nidhi
    Qayum, Arem
    Raina, Arun
    Shankar, Ravi
    Gairola, Sumeet
    Singh, Shashank
    Sangwan, Payare L.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 145 : 511 - 523
  • [9] Synthesis, in vitro anticancer and antimicrobial evaluation of novel substituted dihydropyrimidines
    Rana, K.
    Arora, A.
    Bansal, S.
    Chawla, R.
    INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2014, 76 (04) : 339 - 347
  • [10] Synthesis and evaluation of in vitro anticancer activity of novel solasodine derivatives
    Zha, Xiao Ming
    Zhang, Fei Ran
    Shan, Jia Qi
    Zhang, Yi Hua
    Liu, Jun O.
    Sun, Hong Bin
    CHINESE CHEMICAL LETTERS, 2010, 21 (09) : 1087 - 1090