Silatrane-sulfonamide hybrids: Synthesis, characterization, and evaluation of biological activity

被引:12
作者
Adamovich, Sergey N. [1 ]
Ushakov, Igor A. [1 ]
Oborina, Elizaveta N. [1 ]
Vashchenko, Alexander V. [1 ]
机构
[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, 1 Favorsky St, Irkutsk 664033, Russia
关键词
Silatrane; Sulfonamide; Hybrids; Antimicrobial activity; DRUG DISCOVERY; VINYLSILANES; DESIGN; AMIDES;
D O I
10.1016/j.jorganchem.2021.122150
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of novel sulfonamide-bridged silatranes 3,4,6,7 has been synthesized by the reaction of N,N-dichloroarylsulfonamides la-d with 1-vinylsilatrane 2 and 1-allylsilatrane 5. The structure of the silatrane-sulfonamide hybrids is characterized by elemental analysis, FT-IR, NMR (H-1, C-13, Si-29 and N-15) spectroscopy, high-resolution mass spectrometry, and X-ray diffraction analysis. The resulting hybrids 4ad and 7a-d have been investigated by computational screening via ADMET and PASS. These compounds exhibit drug-like features, bioavailability and may have high enzyme-inhibitory activity. The screening (in vitro) of hybrids 4a,b,d and 7a,b for antimicrobial activities against pathogenic bacterial strains shows that these compounds possess antibacterial properties. (C) 2021 Elsevier B.V. All rights reserved.
引用
收藏
页数:10
相关论文
共 61 条
  • [11] Design and Applications of Bifunctional Small Molecules: Why Two Heads Are Better Than One
    Corson, Timothy W.
    Aberle, Nicholas
    Crews, Craig M.
    [J]. ACS CHEMICAL BIOLOGY, 2008, 3 (11) : 677 - 692
  • [12] Synthesis, characterization and antimicrobial activity of some novel 4-(4-(arylamino)-6-(piperidin-1-yl)-1,3,5-triazine-2-ylamino)-N-(pyrimidin-2-yl)benzenesulfonamides
    Desai, N. C.
    Makwana, Atul H.
    Senta, R. D.
    [J]. JOURNAL OF SAUDI CHEMICAL SOCIETY, 2016, 20 (06) : 686 - 694
  • [13] Switching the site-selectivity of C-H activation in aryl sulfonamides containing strongly coordinating N-heterocycles
    Dong, Yi
    Zhang, XuePeng
    Chen, Jiajing
    Zou, Wenxing
    Lin, Songwen
    Xu, Heng
    [J]. CHEMICAL SCIENCE, 2019, 10 (38) : 8744 - 8751
  • [14] N-Pyrrylarylsulfones with High Therapeutic Potential
    Famiglini, Valeria
    Castellano, Sabrina
    Silvestri, Romano
    [J]. MOLECULES, 2017, 22 (03):
  • [15] Heterocyclization and solvent interception upon oxidative triflamidation of allyl ethers, amines and silanes
    Ganin, Anton S.
    Moskalik, Mikhail Yu
    Astakhova, Vera V.
    Sterkhova, Irina, V
    Shainyan, Bagrat A.
    [J]. TETRAHEDRON, 2020, 76 (33)
  • [16] Synthesis, anticancer and radiosensitizing evaluation of some novel sulfonamide derivatives
    Ghorab, Mostafa M.
    Ragab, Fatma A.
    Heiba, Helmy I.
    El-Gazzar, Marwa G.
    Zahran, Sally S.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 : 682 - 692
  • [17] Treatment of Human Plague: A Systematic Review of Published Aggregate Data on Antimicrobial Efficacy, 1939-2019
    Godfred-Cato, Shana
    Cooley, Katharine M.
    Fleck-Derderian, Shannon
    Becksted, Heidi A.
    Russell, Zachary
    Meaney-Delman, Dana
    Mead, Paul S.
    Nelson, Christina A.
    [J]. CLINICAL INFECTIOUS DISEASES, 2020, 70 : S11 - S19
  • [18] The Structural and Functional Basis for Recurring Sulfa Drug Resistance Mutations in Staphylococcus aureus Dihydropteroate Synthase
    Griffith, Elizabeth C.
    Wallace, Miranda J.
    Wu, Yinan
    Kumar, Gyanendra
    Gajewski, Stefan
    Jackson, Pamela
    Phelps, Gregory A.
    Zheng, Zhong
    Rock, Charles O.
    Lee, Richard E.
    White, Stephen W.
    [J]. FRONTIERS IN MICROBIOLOGY, 2018, 9
  • [19] Possibility of Protic Ionic Liquids Formation From Triethanolamine with Sulfonamides
    Gruzdev, M. S.
    Krestyaninov, M. A.
    Krylov, E. N.
    Shmukler, L. E.
    Safonova, L. P.
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2018, 122 (25) : 6586 - 6594
  • [20] Rh-catalyzed alkene oxidation:: a highly efficient and selective process for preparing N-alkoxysulfonyl aziridines
    Guthikonda, Kiran
    Wehn, Paul M.
    Caliando, Brian J.
    Du Bois, J.
    [J]. TETRAHEDRON, 2006, 62 (49) : 11331 - 11342