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Synthesis and antimicrobial and antinociceptive activity of 4-substituted 2-trichloromethyl-3H-1,5-benzodiazepines

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Abstract

The reaction of 1-substituted 4,4,4-trichloromethylbutane-1,3-diones with o-phenylenediamine afforded 4-substituted 2-trichloromethyl-3H-1,5-benzodiazepines with antimicrobial and antinociceptive activities.

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References

  1. J. B. Paine, J. R. Brough, K. K. Buller, E. E. Erikson, J. Org. Chem., 1987, 52, 3986; DOI: https://doi.org/10.1021/jo00227a009.

    Article  CAS  Google Scholar 

  2. W. A. Kleschick, J. Bordner, J. Heterocycl. Chem., 1989, 26, 1489; DOI: https://doi.org/10.1002/jhet.5570260545.

    Article  CAS  Google Scholar 

  3. B. Lu Wang, Y. W. Jiang, Y. H. Zhang, D. W. Ma, Org. Lett., 2008, 10, 2761; DOI: https://doi.org/10.1021/ol800900a.

    Article  Google Scholar 

  4. M. A. P. Martins, A. Sinhorin, N. E. K. Zimmermann, H. G. Bonacorso, N. Zanatta, G. P. A. Bastos, Synthesis, 2001, 13, 1959; DOI: https://doi.org/10.1055/s-2001-17701.

    Article  Google Scholar 

  5. M. A. P. Martins, A. F. C. Flores, G. P. Bastos, A. Sinhorin, H. G. Bonacorso, N. Zanatta, Tetrahedron Lett., 2000, 41, 293; DOI: https://doi.org/10.1016/S0040-4039(99)02047-X.

    Article  CAS  Google Scholar 

  6. M. A. P. Martins, R. A. Freitag, A. Rosa, A. F. C. Flores, N. Zanatta, H. G. Bonacorso, J. Heterocycl. Chem., 1999, 36, 217; DOI: https://doi.org/10.1002/jhet.5570360133.

    Article  CAS  Google Scholar 

  7. A. F. C. Flores, G. M. Siqueira, R. Freitag, N. Zanatta, M. A. P. Martins, Quim Nova, 1994, 17(4), 298.

    CAS  Google Scholar 

  8. H. G. Bonacorso, S. R. Bittencout, A. D. Wastowski, A. P. Wenz, N. Zanatto, M. A. Martins, J. Hetecocycl. Chem., 1999, 36, 45; DOI: https://doi.org/10.1002/jhet.5570360108.

    Article  CAS  Google Scholar 

  9. P. Aastha, K. Navneet, A. Anshu, S. Pratima, K. R. Dharma, Res. J. Chem. Sci., 2013, 3, 90.

    Google Scholar 

  10. A. Misra, D. Kishore, V. P. Verma, S. Dubey, S. Chander, N. Gupta, S. Bhagyawant, J. Dwivedi, Z. A. Alothman, S. M. Wabaidur, S. Sharma, J. King-Saud-Univ. Sci., 2020, 32, 1486; DOI: https://doi.org/10.1016/j.jksus.2019.12.002.

    Article  Google Scholar 

  11. D. Donati, A. Ursini, M. Korsi, WO Patent WO95/03285 2005, 2135485.

  12. A. A. Gaponov, E. T. Zlenko, S. V. Shishkina, O. V. Shishkin, O. M. Antypenko, S. V. Tretiakov, V. A. Palchikov, Med. Chem. Res., 2016, 25, 1768; DOI: https://doi.org/10.1007/s00044-016-1605-z.

    Article  CAS  Google Scholar 

  13. W. Ben-Cherif, R. Gharbi, H. Sebai, D. Dridi, N. A. Boughattas, M. Ben-Attia, C. R. Biol., 2010, 333, 214; DOI: https://doi.org/10.1016/j.crvi.2009.09.015.

    Article  CAS  Google Scholar 

  14. A. Misra, J. Dwivedi, S. Shukla, D. Kishore, S. Sharma, J. Heterocycl. Chem., 2020, 57, 1545; DOI: https://doi.org/10.1002/jhet.3879.

    Article  CAS  Google Scholar 

  15. A. I. Samigullina, A. T. Gubaidullin, L. V. Mustakimova, V. A. Mamedov, Russ. Chem. Bull., 2014, 63, 1444; DOI: https://doi.org/10.1007/s11172-014-0617-4.

    Article  CAS  Google Scholar 

  16. G. Ahumada, D. Carrillo, C. Manzur, M. Fuentealba, T. Roisnel, J. R. Hamon, J. Mol. Struct., 2016, 1125, 781; DOI: https://doi.org/10.1016/j.molstruc.2016.07.047.

    Article  CAS  Google Scholar 

  17. E. S. Lang, H. G. Bonacorso, S. R. T. Bittencourt, Z. Kristallogr. — New Cryst. Struct., 2000, 215, 242; DOI: https://doi.org/10.1515/ncrs-2000-0225.

    Article  CAS  Google Scholar 

  18. A. Bondi, J. Phys. Chem., 1964, 68, 441; DOI: https://doi.org/10.1021/j100785a001.

    Article  CAS  Google Scholar 

  19. G. R. Desiraju, P. S. Ho, L. Kloo, A. C. Legon, R. Marquardt, P. Metrangolo, P. Politzer, G. Resnati, K. Rissanen, Pure Appl. Chem., 2013, 85, 1711; DOI: https://doi.org/10.1351/PAC-REC-12-05-10.

    Article  CAS  Google Scholar 

  20. N. F. Izmerov, I. V. Sanotskiy, K. K. Sidorov, Parametry toksikometrii promyshlennykh yadov pri odnokratnom vozdeistvii [Toxicometric Parameters of Industrial Toxic Chemicals under Single Exposure], Meditsina, Moscow, 1977, 196 (in Russian).

    Google Scholar 

  21. V. E. Kolla, B. Ya. Syropyatov, Dosy lekarstvennykh sredstv I khimicheskikh soedinenii dlya laboratornykh zhivotnykh [Doses of Medicinal Preparations and Chemical Compounds for Laboratory Animals], Meditsina, Moscow, 1998, 263 pp. (in Russian).

    Google Scholar 

  22. H. Bekker, P. Bekket, W. Berger, K. Gewald, Organikum. Organisch-chemisches Grundpraktikum, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2004.

    Google Scholar 

  23. A. F. C. Flores, M. J. Martins, L. M. Frigo, P. Machado, P. T. Campos, J. L. Malavolta, Synth. Commun., 2012, 42, 727; DOI: https://doi.org/10.1080/00397911.2010.530376.

    Article  CAS  Google Scholar 

  24. CrysAlisPro, Agilent Technologies, Version 1.171.37.33.

  25. G. M. Sheldrick, Acta Cryst., 2008, A64, 112; DOI: https://doi.org/10.1107/S0108767307043930.

    Article  Google Scholar 

  26. G. M. Sheldrick, Acta Cryst., 2015, C71, 3; DOI: https://doi.org/10.1107/S2053229614024218.

    Google Scholar 

  27. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. J. Puschmann, Appl. Cryst., 2009, 42, 339; DOI: https://doi.org/10.1107/S0021889808042726.

    Article  CAS  Google Scholar 

  28. G. N. Pershin, Metody experimental’noi khimioterapii [Methods of Experimental Chemotherapy], Meditsina, Moscow, 1971, 109 (in Russian).

    Google Scholar 

  29. A. N. Mironov, Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh sredstv [Manual on Preclinical Studies of Pharmaceuticals], Grif i K, Moscow, 2012, 944 pp. (in Russian).

    Google Scholar 

  30. Rukovodstvo po experimental’nomu (doklinicheskomu) izucheniyu novyh farmakologicheskih veschestv [Manual on Experimental (Preclinical) Study of New Pharmacological Substances], Ed. R. U. Khabriev, Meditsina, Moscow, 2005, 832 pp. (in Russian).

    Google Scholar 

  31. Metodicheskie rekomendacii po izucheniyu obshchetoksicheskogo deistviya farmakologicheskikh sredstv (utv. 25.12.97) [Regulatory Guidance for General Toxicity Studies of Pharmacological Agents (approved 25.12.97)], Vestn. Farmacop. Komiteta [Bull. Pharmacop. Committee], 1998, 1, 27 (in Russian).

  32. Rukovodstvo “Laboratornye zhivotnye” [Manual “Laboratory Animals”], OOO Irbis, Moscow, 2003 (in Russian).

  33. Rukovodstvo P 1.2.3156-13 “Otsenka toksichnosti i opasnosti khimicheskikh veshchestv i ikh smesei dlya zdorov’ya cheloveka” [Guidance R 1.2.3156-13. “Evaluation of the Toxicity and Hazards of Chemical Substances and Their Mixtures for Human Health”], Federal’nyj centr gigieny i epidemiologii [Federal Center for Sanitary and Epidemiological Supervision], Moscow, 2014, 639 (in Russian).

  34. N. B. Eddy, D. J. Leimbarh, Pharmacoland Exper. Gher., 1953, 385.

  35. M. L. Belen’kii, Elementy kolichestvennoi otsenki farmakologicheskogo effekta [Elements of Quantitative Assessment of Pharmacological Effect], Medgiz, Leningrad, 1963, 152 (in Russian).

    Google Scholar 

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Authors and Affiliations

  1. Perm State University, 15 ul. Bukireva, 614990, Perm, Russian Federation

    O. A. Myshkina, S. Yu. Balandina, R. R. Makhmudov, M. V. Dmitriev & N. Yu. Lisovenko

  2. Federal Scientific Center for Medical and Preventive Health Risk Management Technologies, 82 ul. Monastyrskaya, 614045, Perm, Russian Federation

    R. R. Makhmudov

Authors
  1. O. A. Myshkina
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  2. S. Yu. Balandina
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  3. R. R. Makhmudov
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  4. M. V. Dmitriev
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  5. N. Yu. Lisovenko
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Correspondence to N. Yu. Lisovenko.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1408–1414, July, 2021.

The authors declare no competing interests.

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Myshkina, O.A., Balandina, S.Y., Makhmudov, R.R. et al. Synthesis and antimicrobial and antinociceptive activity of 4-substituted 2-trichloromethyl-3H-1,5-benzodiazepines. Russ Chem Bull 70, 1408–1414 (2021). https://doi.org/10.1007/s11172-021-3232-1

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  • DOI: https://doi.org/10.1007/s11172-021-3232-1

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