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New lactam-containing benzenesulfonamides: design, synthesis, and in silico and in vitro studies

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Abstract

A virtual set of new lactam-containing derivatives of arylsulfonylglycines 1a–d and 2a–d was designed and analyzed using structure–activity computer models (web-services PASS Online, AntiBac-Pred, and GUSAR Acutetoxicity). The antimicrobial activity against Staphylococcus aureus along with low toxicity was predicted for these derivatives. Compounds 1a–d and 2a–d were synthesized by the reactions of N-trimethylsilyl lactams with 4-substituted [(phenyl)sulfonyl]aminoacetyl chlorides. The structures of new compounds were confirmed by IR spectroscopy, NMR spectroscopy, and elemental analysis data. According to the results of studies in vitro, compounds 1a–d and 2a–d efficiently suppress the growth of S. aureus. Lactam-containing benzenesulfonamides bearing the bromine atom or methyl or nitro group at position 4 manifested the most pronounced activity.

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References

  1. N. A. Semina, E. P. Kovaleva, V. G. Akimkin, E. P. Sel’kova, I. A. Khrapunova, Profilaktika vnutribol’nichnogo infitsirovaniya meditsinskikh rabotnikov: prakticheskoe rukovodstvo [Prophylaxis of Intrahospital Infection of Medical Workers: A Practical Guide], Izd-vo RAMN, Moscow, 2006, 152 pp. (in Russian).

    Google Scholar 

  2. H. C. Neu, T. D. Gootz, in Medical Microbiology, Ed. S. Baron, The University of Texas Medical Branch at Galveston, Galveston, 1996.

  3. K. C. Van Meter, R. J. Hubert, in Microbiology for the Healthcare Professional, Elsevier, China, 2016, pp. 214–232.

    Google Scholar 

  4. V. M. Varagić, M. P. Milośević, Farmakologija, Elitmedica, Beograd, 2009, pp. 622–6

    Google Scholar 

  5. I. A. Sytinskii, Gamma-aminomaslyanaya kislota–mediator tormozheniya [γ-Aminobutyric Acid as an Inhibition Mediator], Nauka, Leningrad, 1977, 139 pp. (in Russian).

    Google Scholar 

  6. S. I. Shestakova, S. S. Kukalenko, Laktamy i ikh fiziologicheskaya aktivnost’ [Lactams and Their Physiological Activity], NIITEKhim, Moscow, 1981, pp. 1–37 (in Russian).

    Google Scholar 

  7. D. A. Borozdenko, D. N. Lyakhman, Ya. V. Golubev, D. V. Tarasenko, N. M. Kiseleva, Vad. V. Negrebetsky, Vestn. RGMU [Bulletin of Russian State Medical University], 2020, No. 1, 49–56 (in Russian).

  8. O. S. Stepanova, G. A. Mazurenko, N. Van Tkho, N. Ya. Derkach, in Fiziologicheski aktivnye veshchestva. Vyp. 8, Respubl. mezhved. sbornik [Physiologically Active Substances. Issue 8. Republic Interdepartmental Collection of Works], Naukova Dumka, Kiev, 1978, pp. 86–88 (in Russian).

    Google Scholar 

  9. A. D. Shagina, E. P. Kramarova, A. G. Shipov, D. V. Tarasenko, Vad. V. Negrebetsky, Yu. I. Baukov, Russ. Chem. Bull., 2020, 69, 398–400.

    Article  CAS  Google Scholar 

  10. M. Rothe, T. Tóth, R. Daser, Chem. Ber., 1966, 99, 3820–3829.

    Article  CAS  Google Scholar 

  11. Author’s Certificate 931104 USSR; Byul. Izobret. [Invention Bulletin], 1982, No. 19 (in Russian).

  12. H. R. Kricheldorf, E. Leppert, Synthesis, 1975, 592–593.

  13. H. R. Kricheldorf, Makromol. Chem., 1973, 170, 89–103.

    Article  CAS  Google Scholar 

  14. N. A. Anisimova, I. Yu. Belavin, Yu. I. Baukov, in Khimiya i prakticheskoe primenenie kremnii- i fosfororganicheskikh soedinenii (Mezhvuz. sb. nauchn. Trudov [Chemistry and Practical Use of Silicon- and Phosphorus-Containing Organic Compounds (Interuniversity Collection of Scientific Works], Leningrad Technological Institute named after Lensovet, Leningrad, 1980, pp. 18–21 (in Russian).

    Google Scholar 

  15. E. P. Kramarova, Yu. I. Baukov, in Khimiya i prakticheskoe primenenie kremnii- i fosfororganicheskikh soedinenii (Mezhvuz. sb. nauchn. Trudov [Chemistry and Practical Use of Silicon- and Phosphorus-Containing Organic Compounds (Interuniversity Collection of Scientific Works], Leningrad Technological Institute named after Lensovet, Leningrad, 1980, pp. 21–23 (in Russian).

    Google Scholar 

  16. N. A. Anisimova, E. P. Kramarova, I. Yu. Belavin, Yu. I. Baukov, Zh. Obshch. Khim. [Sov. J. Gen. Chem.], 1986, 56, 1845–1853 (in Russian).

    CAS  Google Scholar 

  17. A. I. Konovalov, I. S. Antipin, V. A. Burilov, T. I. Madzhidov, A. R. Kurbangalieva, A. V. Nemtarev, S. E. Solovieva, I. I. Stoikov, V. A. Mamedov, L. Ya. Zakharova, E. L. Gavrilova, O. G. Sinyashin, I. A. Balova, A. V. Vasiliev, I. G. Zenkevich, M. Yu. Krasavin, M. A. Kuznetsov, A. P. Molchanov, M. S. Novikov, V. A. Nikolaev, L. L. Rodina, A. F. Khlebnikov, I. P. Beletskaya, S. Z. Vatsadze, S. P. Gromov, N. V. Zyk, A. T. Lebedev, D. A. Lemenovsky, V. S. Petrosyan, V. G. Nenaydenko, Vad. V. Negrebetsky, Yu. I. Baukov, T. A. Shmigol, A. A. Korlyukov, A. S. Tikhomirov, A. E. Shchekotikhin, V. F. Traven, L. G. Voskresensky, F. I. Zubkov, O. A. Golubchikov, A. S. Semeikin, D. B. Berezin, P. A. Stuzhin, V. D. Filimonov, E. A. Krasnokutskaya, A. Yu. Fedorov, A. V. Nyuchev, A. Yu. Orlov, R. S. Begunov, A. I. Rusakov, A. V. Kolobov, E. R. Kofanov, O. V. Fedotova, A. Yu. Egorova, V. N. Charushin, O. N. Chupakhin, Y. N. Klimochkin, V. A. Osyanin, A. N. Reznikov, A. S. Fisyuk, G. P. Sagitullina, A. V. Aksenov, N. A. Aksenov, M. K. Grachev, V. I. Maslennikova, M. P. Koroteev, A. K. Brel, S. V. Lisina, S. M. Medvedeva, Kh. S. Shikhaliev, G. A. Suboch, M. S. Tovbis, L. M. Mironovich, S. M. Ivanov, S. V. Kurbatov, M. E. Kletskiy, O. N. Burov, K. I. Kobrakov, D. N. Kuznetsov, Russ. J. Org. Chem., 2018, 54, 161–360.

    Article  Google Scholar 

  18. Vad. V. Negrebetsky, S. V. Vorobiev, E. P. Kramarova, A. G. Shipov, T. A. Shmigol, Yu. I. Baukov, A. A. Lagunin, A. A. Korlyukov, D. E. Arkhipov, Russ. Chem. Bull., 2019, 67, 1518–1529.

    Article  Google Scholar 

  19. A. A. Korlyukov, D. E. Arkhipov, A. D. Volodin, Vad. V. Negrebetsky, A. A. Nikolin, E. P. Kramarova, A. G. Shipov, Yu. I. Baukov, Russ. Chem. Bull., 2019, 68, 137–148].

    Article  CAS  Google Scholar 

  20. A. A. Nikolin, A. A. Korlyukov, E. P. Kramarova, D. E. Arkhipov, A. G. Shipov, Yu. I. Baukov, Vad. V. Negrebetsky, Russ. Chem. Bull., 2019, 68, 1575–1579.

    Article  CAS  Google Scholar 

  21. A. A. Lagunin, A. V. Stepanchikova, D. A. Filimonov, V. V. Poroikov, Bioinformatics, 2000, 16, 747–748.

    Article  CAS  Google Scholar 

  22. D. A. Filimonov, A. A. Lagunin, T. A. Gloriozova, A. V. Rudik, D. S. Druzhilovskii, P. V. Pogodin, V. V. Poroikov, Chem. Heterocycl. Compd., 2014, 50, 444–457.

    Article  CAS  Google Scholar 

  23. P. V. Pogodin, A. A. Lagunin, A. V. Rudik, D. S. Druzhilovskiy, D. A. Filimonov, V. V. Poroikov, J. Chem. Inf. Model., 2019, 59, 4513–4518.

    Article  CAS  Google Scholar 

  24. A. Gaulton, A. Hersey, M. Nowotka, A. P. Bento, J. Chambers, D. Mendez, P. Mutowo, F. Atkinson, L. J. Bellis, E. Cibrián-Uhalte, M. Davies, N. Dedman, A. Karlsson, M. P. Magariños, J. P. Overington, G. Papadatos, I. Smit, A. R. Leach, Nucleic Acids Res., 2017, 45, 945–954.

    Article  Google Scholar 

  25. A. A. Lagunin, A. V. Zakharov, D. A. Filimonov, V. V. Poroikov, Mol. Inform., 2011, 30, 241–250.

    Article  CAS  Google Scholar 

  26. A. G. Shipov, E. P. Kramarova, Vad. V. Negrebetsky, V. I. Akhapkina, S. A. Pogozhikh, Yu. I. Baukov, Vestn. RGMU [Bulletin of Russian State Medical University], 2006, No. 1, 56–61 (in Russian).

  27. J. DeRuiter, A. N. Brubaker, M. A. Garner, J. M. Barksdale, C. A. Mayfield, J. Pharm. Sci., 1987, 76, 149–152.

    Article  CAS  Google Scholar 

  28. L. Birkofer, P. Richter, A. Ritter, Chem. Ber., 1960, 93, 2804–2809.

    Article  CAS  Google Scholar 

  29. V. Prisacari, in Ghid de supraveghere şi control în infecţiile nosocomiale, Coord. şt V. Prisacari, Chişinău, 2008, p. 48–57; http://89.32.227.76/_files/3514-Ghid_INV_PHH.pdf (in Romanian).

  30. V. Prisacari, I. Berdeu, Akademos, 2014, Nr. 1 (32), 92–100; http://www.akademos.asm.md/files/Problema%20antibioticorezistentei%20bicrobiene.pdf (in Romanian).

  31. Opredelenie chuvstvitel’nosti mikroorganizmov k antibakterial’nym preparatam. Metodicheskie ukazaniya [Determination of Sensitivity of Microorganisms to Antibacterial Drugs. Methodical Guideline], MUK 4.2.1890-04 approved by Head Sanitary Inspector of the Russian Federation of 04.03.2004 (in Russian).

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Authors and Affiliations

  1. Pirogov Russian National Research Medical University, 1 ul. Ostrovityanova, 117997, Moscow, Russian Federation

    A. D. Shagina, E. P. Kramarova, D. V. Tarasenko, D. I. Gonchar, D. N. Lyakhman, A. A. Lagunin, K. A. Sobyanin, T. A. Shmigol’, Yu. I. Baukov & Vad. V. Negrebetsky

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  1. A. D. Shagina
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  2. E. P. Kramarova
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  3. D. V. Tarasenko
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  4. D. I. Gonchar
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  5. D. N. Lyakhman
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  6. A. A. Lagunin
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  7. K. A. Sobyanin
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  8. T. A. Shmigol’
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  9. Yu. I. Baukov
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Correspondence to A. D. Shagina.

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This work was financially supported by the Russian Foundation for Basic Research (Project No. 20-03-00858).

This work does not involve human participants and animal subjects.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 479–486, March, 2021.

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Shagina, A.D., Kramarova, E.P., Tarasenko, D.V. et al. New lactam-containing benzenesulfonamides: design, synthesis, and in silico and in vitro studies. Russ Chem Bull 70, 479–486 (2021). https://doi.org/10.1007/s11172-021-3112-8

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  • DOI: https://doi.org/10.1007/s11172-021-3112-8

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