Synthesis and Biological Evaluation of N-Aminoalkil Derivatives of Sulfanilamide Reaction

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

A series of 19 derivatives of sulfanilamide was synthesized by the reaction of chloroacetamide, trichloroacetamide and chloropropionamide with N-nucleophiles. It was shown that N-trichloroacetylsulfanilamide in reactions with amines forms products of substitution of the trichloromethyl group, while N-chloroacetylsulfanilamide and N-chloropropionylsulfanilamide react with substitution of the halogen atom. An assessment of the antibacterial properties of the synthesized structures was carried out, showing the absence of activity with respect to E. coli and St. aureus strains. Two aminoalkyl-containing sulfonamides – 2-(4-benzylpiperidin-1-yl)-N-(4-sulfamoylphenyl)acetamide and 2-(4-nitropyrazol-1-yl)-N-(4-sulfamoylphenyl)acetamide – showed inhibitory properties against the human monoamine oxidase enzyme, comparable in IC50 value to the drug zonisamide.

Толық мәтін

Рұқсат жабық

Авторлар туралы

Elena Vasilyeva

Ushinsky Yaroslavl State Pedagogical University; Kosygin Russian State University

Email: a.shetnev@yspu.org
ORCID iD: 0000-0001-6855-0883
Ресей, Yaroslavl; Moscow

Irina Proskurina

Ushinsky Yaroslavl State Pedagogical University

Email: a.shetnev@yspu.org
ORCID iD: 0000-0001-6086-1978
Ресей, Yaroslavl

Anton Shetnev

Ushinsky Yaroslavl State Pedagogical University; Moscow Institute of Physics and Technology

Хат алмасуға жауапты Автор.
Email: a.shetnev@yspu.org
ORCID iD: 0000-0002-4389-461X
Ресей, Yaroslavl; Dolgoprudny

Anna Romanycheva

Ushinsky Yaroslavl State Pedagogical University

Email: a.shetnev@yspu.org
ORCID iD: 0000-0002-7931-1711
Ресей, Yaroslavl

Alyona Korovina

Ushinsky Yaroslavl State Pedagogical University

Email: a.shetnev@yspu.org
ORCID iD: 0009-0003-5743-6948
Ресей, Yaroslavl

Maria Belchenko

Ushinsky Yaroslavl State Pedagogical University

Email: a.shetnev@yspu.org
ORCID iD: 0009-0006-9589-0756
Ресей, Yaroslavl

Ekaterina Grunina

Ushinsky Yaroslavl State Pedagogical University

Email: a.shetnev@yspu.org
ORCID iD: 0009-0007-4551-1866
Ресей, Yaroslavl

Anelle Petzer

North-West University

Email: a.shetnev@yspu.org
ORCID iD: 0000-0001-8114-8223
ОАР, Potchefstroom

Alexander Kotov

Ushinsky Yaroslavl State Pedagogical University

Email: a.shetnev@yspu.org
ORCID iD: 0000-0002-0567-2880
Ресей, Yaroslavl

Jacob Petzer

North-West University

Email: a.shetnev@yspu.org
ORCID iD: 0000-0002-7114-8120
ОАР, Potchefstroom

Әдебиет тізімі

  1. Scholar E. // xPharm: The Comprehensive Pharmacology Reference. 2007. P. 1. doi: 10.1016/b978-008055232-3.62694-7
  2. Курышева Н.И. // Офтальмология. 2020. Т. 17. № 4. С. 676. doi: 10.18008/1816-5095-2020-4-676-682
  3. Abdel-Aziz A., El-Azab A.S., Abou-Zeid L.A., Eltahir K.E., Abdel-Aziz N.I., Ayyad R.R., Al-Obaid A.M. // Eur. J. Med. Chem. 2016. Vol. 115. P. 121. doi 10.1016/ j.ejmech.2016.03.011.
  4. Bua S., Osman M., Al-Othman Z., Supuran C., Nocentini A. // Bioorg. Chem. 2019. Vol. 86. P. 39. doi 10.1016/ j.bioorg.2019.01.030
  5. El-Azab A., Abdel-Aziz A., Bua S., Nocentini A., El-Gendy M., Mohamed M., Shawer T., Al-Saif N., Supuran C. // Bioorg. Chem. 2019. Vol. 87. P. 78. doi 10.1016/ j.bioorg.2019.03.007
  6. Tanini D., Capperucci A., Scopelliti M., Milaneschi A., Angeli A., Supuran C. // Bioorg. Chem. 2019. Vol. 89. P. 102984. doi: 10.1016/j.bioorg.2019.102984
  7. Krymov S.K., Salnikova D.I., Dezhenkova L.G., Bogdanov F.B., Scherbakov A.M., Shchekotikhin A.E. // Chem. Heterocycl. Compd. 2024. Vol. 60. P. 473. doi: 10.1007/s10593-024-03365-5
  8. Kandile N.G., Elzamly R.A., Mohamed M.I., Zaky H.T., Harding D.R.K., Mohamed H.M. // Int. J. Biol. Macromol. 2023. Vol. 239. P. 1. doi: 10.1016/j.ijbiomac.2023.124280
  9. Ibrahim H., Eldehna W., Abdel-Aziz H., Elaasser M., Abdel-Aziz M. // Eur. J. Med. Chem. 2014. Vol. 85. P. 480. doi: 10.1016/j.ejmech.2014.08.016
  10. Singh P., Purnachander Yadav P., Swain B., Thacker P., Angeli A., Supuran C., Arifuddin M. // Bioorg. Chem. 2021. Vol. 108. Art. 104647. doi 0.1016/ j.bioorg.2021.104647
  11. Krasavin M., Shetnev A., Baykov S., Kalinin S., Nocentini A., Sharoyko V., Poli G., Tuccinardi T., Korsakov M., Tennikova T., Supuran Claudiu T. // Eur. J. Med. Chem. 2019. Vol. 168. P. 301. doi: 10.1016/j.ejmech.2019.02.044
  12. Turkmen H., Durgun M., Yilmaztekin S., Emul M., Innocenti A., Vullo D., Supuran C. // Bioorg. Med. Chem. Lett. 2005. Vol. 15. N 2. P. 367. doi: 10.1016/j.bmcl.2004.10.070
  13. Georgey H., Manhi F., Mahmoud W., Mohamed N., Berrino E., Supuran C. // Bioorg. Chem. 2019. Vol. 82. P. 109. doi: 10.1016/j.bioorg.2018.09.037
  14. Mishra C.B., Kumari S., Angeli A., Monti S.M., Buonanno M., Ti‐wari M., Supuran C. // J. Med. Chem. 2017. Vol. 60. N 6. P. 2456. doi: 10.1021/acs.jmedchem.6b01804
  15. Hanan H., Georgey F., Manhi W., Mahmoud N., Mohamed E.B., Supuran C. // Bioorg. Chem. 2019. Vol. 82. P. 109. doi: 10.1016/j.bioorg.2018.09.037
  16. Khokhlov A.L., Yaichkov I.I., Korsakov M.K., Shetnev A.A., Ivanovskiy S.A., Alexeev M.A., Gasilina O.A., Volkhin N.N., Petukhov S.S. // Res. Results Pharmacol. 2024. Vol. 10. N 1. P. 53. doi: 10.18413/rrpharmacology.10.431
  17. Shetnev A., Efimova J., Gasilina O., Shabalina E., Baykov B., Lifanov D., Petersen E., Korsakov M., Petzer A., Petzer J.P. // Med. Chem. Res. 2025. Vol. 34. P. 357. doi: 10.1007/s00044-024-03346-5
  18. Sağlık B.N., Osmaniye D., Acar Çevik U., Levent S., Kaya Çavuşoğlu B., Atlı Eklioğlu Ö., Kaplancıklı Z.A. // J. Enzyme Inhib. Med. Chem. 2020. Vol. 35. N 1. P. 1422. doi: 10.1080/14756366.2020.1784892
  19. Alafeefy A.M., Ceruso M., Al-Tamimi A.M.S., Del Prete S., Capasso C., Supuran C. // Bioorg. Med. Chem. 2014. Vol. 22. N 19. P. 5133. doi: 10.1016/j.bmc.2014.08.015
  20. Turkmen H., Durgun M., Yilmaztekin S., Emul M., Innocenti A., Vull D., Scozzafava A., Supuran C.T. // Bioorg. Med. Chem. Lett. 2005. Vol. 15. N 2. Р. 367. doi: 10.1016/j.bmcl.2004.10.070
  21. Mahdy H.A., Ibrahim M.K., Metwaly A.M., Belal A., Mehany A.B.M., El-Gamal K.M.A., El-Sharkawy A., Elhendawy M.A., Radwan M.M., Elsohly M.A., Eissa I.H. // Bioorg. Chem. 2019. Vol. 94. P. 103422. doi 10.1016/ j.bioorg.2019.103422
  22. Eissa I.H., Ibrahim M.K., Metwaly A.M., Belal A., Mehany A.B.M., Abdel‐hady A.A., Elhendawy M.A., Radwan M.M., El-Sohly M.A., Mahdy H.A. // Bioorg. Chem. 2021. Vol. 107. P. 104532. doi 10.1016/ j.bioorg.2020.104532
  23. Monforte A.M., Ferro S., De Luca L., Lo Surdo G., Morreale F., Panne‐couque C., Balzarini J., Chimirri A. // Bioorg. Med. Chem. 2014. Vol. 22. N. 4. P. 1459. doi: 10.1016/j.bmc.2013.12.045
  24. Kulabaş N., Tatar E., Bingöl Ö., Özsavcı D., Pannecouque C., De Clercq E., Küçükgüzel İ. // Eur. J. Med. Chem. 2016. Vol. 121. P. 58. doi 10.1016/ j.ejmech.2016.05.017
  25. Lu X., Li X., Yang J., Huang B., Kang D., Zhao F., Zhou Z., De Clercq E., Daelemans D., Pannecouque C., Zhan P., Liu X. // Bioorg. Med. Chem. 2016. Vol. 24. N 18. P. 4424. doi 10.1016 /j.bmc.2016.07.041
  26. Mohamed M.M., Khalil A.K., Abbass E.M., El-Naggar A.M. // Synth. Commun. 2017. Vol. 47. N 16. P. 1441. doi: 10.1080/00397911.2017.1332223
  27. Abutayeh R.F., Almaliti J., Taha M.O. // Med. Chem. 2020. Vol. 16. N 3. P. 403. doi 10.2174/ 1573406415666190401144053
  28. Определение чувствительности микроорганизмов к антибактериальным препаратам (МУК 4.2.1890-04) // Клин. микробиол. антимикроб. химиотер. 2004. Т. 6. Вып. 4. C. 306.
  29. Mostert S., Petzer A., Petzer J.P. // Chem. Med. Chem. 2015. Vol. 10. P. 862. doi: 10.1002/cmdc.201500059
  30. Sonsalla P.K., Wong L.Y., Winnik B., Buckley B. // Exp. Neurol. 2010. Vol. 221. P. 329. doi 10.1016/ j.expneurol.2009.11.018
  31. Petzer A., Pienaar A., Petzer J.P. // Drug Res. 2013. Vol. 63. P. 462. doi: 10.1055/s-0033-1345163
  32. Al-Sha’er M.A., Taha M.O. // Med. Chem. Res. 2011. Vol. 21. N 4. P. 487. doi: 10.1007/s00044-011-9557-9
  33. Hu H., Bajorath J. // Mol. Pharm. 2020. Vol. 17. N 3. P. 979. doi: 10.1021/acs.molpharmaceut

Қосымша файлдар

Қосымша файлдар
Әрекет
1. JATS XML
2. Scheme 1.

Жүктеу (110KB)
3. Scheme 2.

Жүктеу (220KB)
4. Scheme 3.

Жүктеу (103KB)
5. Scheme 4.

Жүктеу (166KB)

© Russian Academy of Sciences, 2025