Synthesis, some transformations and antibacterial activity of 5H-spiro[benzo[h][1,2,4]triazolo[3,4-b]quinazoline6,1′-cycloheptane]-7(11H)-ones

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Condensation of 2-thioxo-2,3-dihydro-1 H -spiro[benzo[ h ]quinazoline-5,1′-cycloheptane]-4(6 H )-one with hydrazine hydrate afforded 2-hydrazinyl-3 H -spiro[benzo[ h ]quinazoline-5,1′-cycloheptane]-4(6 H )-one. The reaction of the latter with orthoformic acid ethyl ester or carbon disulfide yielded 5 H -spiro[benzo[ h ][1,2,4]triazolo[3,4- b ]quinazoline-6,1′-cycloheptane]-7(11 H )-one and 9-mercapto-5 H -spiro[benzo[ h ][1,2,4]triazolo[3,4- b ] quinazoline-6,1 ‘-cycloheptane]-7(11 H )-one, respectively. Alkylation of the latter with methyl and ethyl iodides, allyl bromide, and benzyl chloride gave 9-sulfanyl-substituted 5 H -spiro[benzo[ h ][1,2,4]triazolo[3,4- b ]quinazoline-6,1′-cycloheptane]-7(11 H )-ones. The synthesized compounds exhibited antibacterial properties.

作者简介

A. Markosyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

Email: ashot@mаrkosyan.am

A. Ayvazyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

S. Gabrielyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

S. Mamyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

A. Ayvazyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

H. Arakelyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

参考

  1. Gupta R., Chaudhary R.P. // Phosphorus, Sulfur, Silicon, Relat. Elem. 2012. Vol. 187 N 6. P. 735. doi: 10.1080/10426507.2011.647145
  2. Velpula R., Banothu J., Gali R., Sargam Y., Bavantula R. // Turkish J. Chem. 2015. Vol. 39. P. 620. doi: 10.3906/kim-1410-64
  3. Keshari A.K., Singh A.K., Raj V., Rai A., Trivedi P., Ghosh B., Kumar U., Rawat A., Kumar D., Saha S. // Drug Des. Devel. Ther. 2017. Vol. 11. P. 1623. doi: 10.2147/DDDT.S136692
  4. Maurya H.K., Hasanain M., Singh S., Sarkar J., Dubey V., Shukla A., Luqman S., Khanc F., Gupta A. // RSC Adv. 2016. Vol. 6. N 22. P. 18607. doi: 10.1039/C5RA24429C
  5. Wu L., Zhang Ch. // RSC Adv. 2016. Vol. 6. N 34. P. 287555. doi: 10.1039/C6RA03323G
  6. Wu L., Liu Y., Li Y. // Molecules. 2018. Vol. 23. N 9. P. 2330. doi: 10.3390/molecules23092330
  7. Abdelsalam E.A., Zaghary W.A., Amin K.M., Abou Taleb N.A., Mekawey A.A.I., Eldehna W.M., Hatem A.A., Hammad S.F. // Bioorg. Chem. 2019. Vol. 89. Art. no. 102985. doi: 10.1016/j.bioorg.2019.102985
  8. Grover P., Bhardwaj M., Kapoor G., Mehta L., Ghai R., Nagarajan K. // Curr. Org. Chem. 2021. Vol. 25. N 6. P. 695. doi: 10.2174/1385272825666210212121056
  9. Mohareb R.M., Ibrahim R.A., Elmetwally A.M., Gamaan M.S. // Acta Chim. Slov. 2022. Vol. 69. N 1. P. 13. doi: 10.17344/acsi.2021.6733
  10. Roudbaraki S.J., Janghorban S., Ghashang M. // Med. Chem. Nat. Prod. Res. 2019. Vol. 22. N 6. P. 422. doi: 10.2174/1386207322666190617164617
  11. Ohtomo H., Tagata T., Sasaki K., Hirota T., Okuda K. // Tetrahedron. 2007. Vol. 63 N 51. P. 12541. doi: 10.1016/j.tet.2007.10.024
  12. Maurya H.K., Verma R., Alam S., Pandey Sh., Pathak V., Harma S., Srivastava K.K., Negi A.S., Gupta A. // Bioorg. Med. Chem. Lett. 2013. Vol. 23. N 21(1). P. 5844. doi: 10.1016/j.bmcl.2013.08.101
  13. Pozharskii A.F., Ozeryanskii V.A., Mikshiev V.Y., Antonov A.S., Chernyshev A.V., Metelitsa A.V., Borodkin G.S., Fedik N.S., Dyablo O.V. // J. Org. Chem. 2016. Vol. 81. N 13. P. 5574. doi: 10.1021/acs.joc.6b00917
  14. Sahoo M., Jena L., Daf S., Kumar S. // Genomics Inform. 2016. Vol. 14. N 3. P. 104. doi: 10.5808/GI.2016.14.3.104
  15. Маркосян А.И., Айвазян А.С., Габриелян С.А., Мамян С.С., Арсенян Ф.Г., Сафарян А.С., Аракелян А.Г. // Хим.-фарм. ж. 2022. Т. 56. № 9. С. 28. doi: 10.30906/0023-1134-2022-56-9-28-32
  16. Markosyan A.I., Ayvazyan A.S., Gabrielyan S.H., Mamyan S.S., Arsenyan F.H., Safaryan A.S., Arakelyan H.H. // Pharm. Chem. J. 2022. Vol. 56. P. 1183. doi: 10.1007/s11094-022-02774-0
  17. Маркосян А.И., Айвазян А.С., Габриелян С.А., Мамян С.С., Арсенян Ф.Г., Сафарян А.Г., Аракелян А.С. // Хим.-фарм. ж. 2021. Т. 55. № 2. С. 24. doi: 10.30906/0023-1134-2021-55-2-24-28
  18. Markosyan A.I., Ayvazyan A.S., Gabrielyan S.A., Mamyan S.S., Arsenyan F.H., Safaryan A.H, Arakelyan H.S. // Pharm. Chem. J. 2021. Vol. 55. P. 133. doi: 10.1007/s11094-021-02392-2.
  19. Маркосян А.И., Айвазян А.С., Габриелян С.А., Мамян С.С. // ЖОрХ. 2021. Т. 57. № 3. С. 410. doi: 10.31857/S0514749221030095
  20. Markosyan A.I., Ayvazyan A.S., Gabrielyan S.A., Mamyan S.S. // Russ. J. Org. Chem. 2021. Vol. 57. P. 383. doi: 10.1134/S107042802103009X
  21. Маркосян А.И., Айвазян А.С., Габриелян С.А., Мамян С.С., Авакимян Дж.А., Мартиросян Л.А. // Хим.-фарм. ж. 2022 Т. 56. № 10. С. 17. doi: 10.30906/0023-1134-2022-56-10-17-2
  22. Markosyan A.I., Ayvazyan A.S., Gabrielyan S.A., Mamyan S.S., Avakimyan J.A., Martirosyan L.A. // Pharm. Chem. J. 2023. Vol. 56. N 10. P. 1321. doi: 10.1007/s11094-023-02792-6
  23. Маркосян А.И., Куроян Р.А., Диланян С.В., Алексанян М.С., Карапетян А.А., Стручков Ю.Т. // ХГС. 2000. № 5. С. 658
  24. Markosyan A.I., Kuroyan R.A., Dilanyan S.V., Aleksanyan M.S., Karapetyan A.A., Struchkov Yu.T. // J. Heterocycl. Chem. 2000. Vol. 36. P. 574. doi: 10.1007/BF02290848
  25. Маркосян А.И., Куроян Р.А., Диланян С.В. // ХГС. 2000. № 3. С. 396
  26. Markosyan A.I., Kuroyan R.A., Dilanyan S.V. // J. Heterocycl. Chem. 2000. Vol. 36. P. 334. doi: 10.1007/BF02256872
  27. Миронов А.Н. Руководство по проведению доклинических исследований лекарственных средств. М.: Медицина, 2012. С. 509.
  28. Sheldrick G.M. // Acta Crystallogr. (C). 2015. Vol. 71. P. 3. doi: 10.1107/S2053229614024218

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