Synthesis, DFT and Antitumor Activity Screening of Some New Heterocycles Derived from 2,2'-(2-(1,3-Diphenyl-1H-Pyrazol-4-yl)Ethene-1,1-Diyl)Bis(4H-Benzo[d][1,3]Oxazin-4-One)

被引:23
|
作者
Abdelrahman, Aya M. [1 ]
Fahmi, Abdelgawad A. [2 ]
Rizk, Sameh A. [1 ]
El-Helw, Eman A. E. [1 ]
机构
[1] Ain Shams Univ, Fac Sci, Dept Chem, Cairo 11566, Egypt
[2] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt
关键词
Antitumor; DFT; bis-benzoxazinone; bis-triazolethione; pyrazole; RAPID COLORIMETRIC ASSAY; QUINAZOLINONE DERIVATIVES; SURVIVAL; GROWTH;
D O I
10.1080/10406638.2021.2020310
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The broad spectrum of biological activity of pyrazole derivatives coupled with our interest in the chemistry of nitrogen heterocycles led us to synthesize a bis-benzoxazinone derivative bearing a pyrazole scaffold and utilize it as a key material for the construction of some bisimidazole, bistriazole, and bisbenzimidazole derivatives obtained by reactions with some mono- and bidentate nitrogen nucleophiles. The density functional theory studies of the synthesized compounds were calculated. The synthesized compounds were screened for their in vitro antitumor activity against two human tumor cell lines; HepG2 and MCF-7. Some compounds displayed satisfactory activities.
引用
收藏
页码:721 / 739
页数:19
相关论文
共 50 条
  • [41] Unexpected formation of 1,6-bis[3,5-dimethyl-4-(1,4,6-oxadithiocan-5-yl)-1H-pyrazol-1-yl]hexane in the reaction of 1,1’-(hexane-1,6-diyl)bis[3,5-dimethyl-1H-pyrazole-4-carbaldehyde] with 2-sulfanylethanol
    L. K. Papernaya
    E. V. Rudyakova
    A. I. Albanov
    G. G. Levkovskaya
    Russian Journal of Organic Chemistry, 2008, 44 : 1554 - 1555
  • [42] The complex Eu(phen)L3·5CH2Cl2 (HL is 1,3-bis(1,3-dimethyl-1H-pyrazol-4-yl)propane-1,3-dione): synthesis, crystal structure, and luminescent properties
    I. V. Taydakov
    B. E. Zaitsev
    S. S. Krasnosel’skiy
    Z. A. Starikova
    R. S. Borisov
    Russian Chemical Bulletin, 2011, 60 : 1595 - 1600
  • [43] Synthesis, XRD, characterization and antibacterial activity of novel α,β unsaturated carbonyl compound: (Z)-2-((3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one (C26H19ClN2O)
    Dodeja, Khushbu K.
    Bhola, Yogesh O.
    Naliapara, Y. T.
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2021, 714 (01) : 89 - 102
  • [44] Synthesis and crystal structure of 2-((1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)methylene)-2,3-dihydro-1H-inden-1-one, C23H16N2OS
    Alqahtani, Alaa
    Abdel-Wahab, Bakr F.
    Hegazy, Amany S.
    Kariuki, Benson M.
    El-Hiti, Gamal A.
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2019, 234 (05): : 969 - 971
  • [45] The complex Eu(phen)L3•5CH2Cl2 (HL is 1,3-bis(1,3-dimethyl-1H-pyrazol-4-yl)propane-1,3-dione): synthesis, crystal structure, and luminescent properties
    Taydakov, I. V.
    Zaitsev, B. E.
    Krasnosel'skiy, S. S.
    Starikova, Z. A.
    Borisov, R. S.
    RUSSIAN CHEMICAL BULLETIN, 2011, 60 (08) : 1595 - 1600
  • [46] Synthesis, biological screening and in silico studies of new N-phenyl-4-(1,3-diaryl-1H-pyrazol-4-yl)thiazol-2-amine derivatives as potential antifungal and antitubercular agents
    Nandurkar, Yogesh
    Bhoye, Manish R.
    Maliwal, Deepika
    Pissurlenkar, Raghuvir R. S.
    Chavan, Abhijit
    Katade, Sushma
    Mhaske, Pravin C.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2023, 258
  • [47] Synthesis of 2,2′-bis(1-(2-aryl)-1H-pyrazol-4-yl)-3,3,3′,3′-tetramethyl-3H,3′H-5,5′-biindoles and 2,7-bis(1-(3-aryl)-1H-pyrazol-4-yl)-1,1,6,6-tetramethyl-1,6-dihydroindolo[7,6-g]indoles
    Rashidi, Ahmad
    Baradarani, Mehdi M.
    Joule, John A.
    ARKIVOC, 2011, : 252 - 259
  • [48] Studies on the synthesis, in vitro antitumor activity of 4H-benzo[h]chromene, 7H-benzo[h]chromene[2,3-d]pyrimidine derivatives and structure–activity relationships of the 2-,3- and 2,3-positions
    Ahmed M. El-Agrody
    Ahmed M. Fouda
    Al-Anood M. Al-Dies
    Medicinal Chemistry Research, 2014, 23 : 3187 - 3199
  • [49] 2-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(4-nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene
    Albooye, Fereshteh
    Kiyani, Hamzeh
    MOLBANK, 2013, (03)
  • [50] Microwave assisted synthesis of substituted (Z)-2-{[1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl]methylene}benzofuran-3(2H)-ones and their antimicrobial activity
    Ashok, D.
    Ziauddin, M.
    Lakshmi, B. Vijaya
    Sarasija, M.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2016, 86 (07) : 1753 - 1757