Mass-spectra of new heterocycles: XXIV. Electron impact and chemical ionization study of N-[3-alkoxyand 3-(1H-pyrrol-1-yl)-2-thienyl]imidothiocarbamates

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Дәйексөз келтіру

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Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

The behavior of a wide range of previously unknown N -(2-thienyl)imidothiocarbamates synthesized in a single preparative step from heterosubstituted allenes (methoxy-, 1-ethoxyethoxy- and 1 H -pyrrol-1-ylallenes) and aliphatic, cycloaliphatic, and aromatic isothiocyanates was studied under conditions of electron (70 eV) and chemical (reagent gas - methane) ionization. Under the electron impact, the studied compounds form an unstable molecular ion, the main direction of fragmentation of which is associated with the breaking of the C-N bond in the imidoformamide fragment with charge localization at the imine nitrogen atom. A similar decay channel of a molecular ion is also observed in the chemical ionization mass spectra of the studied compounds. In this case, characteristic, but low-intensity ions in the electron ionization spectra of N -(3-methoxy-2-thienyl)imidothiocarbamates become dominant in the chemical ionization spectra. In the chemical ionization spectra of N -[3-(1 H -pyrrol-1-yl)-2-thienyl]imidothiocarbamates, the maximum intensity peak belongs to the [ M - SMe]+ ion. For N -[3-(1-ethoxyethoxy)-2-thienyl]imidothiocarbamate, the peak of the ion formed upon successive elimination of ethoxyethene and methanethiol molecules from the [ M + H]+ ion has the maximum intensity.

Авторлар туралы

L. Klyba

Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences

Email: klyba@irioch.irk.ru

E. Sanzheeva

Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences

Email: klyba@irioch.irk.ru

N. Nedolya

Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences

Email: klyba@irioch.irk.ru

O. Tarasova

Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences

Email: klyba@irioch.irk.ru

Әдебиет тізімі

  1. Клыба Л.В., Недоля Н.А., Санжеева Е.Р., Тарасова О.А. ЖОрХ. 2021, 57, 1669-1683.
  2. Klyba L.V., Nedolya N.A., Sanzheeva E.R., Tarasova O.A. Russ. J. Org. Chem. 2021, 57, 1901-1912. doi: 10.1134/S1070428021120022
  3. Joule J.A. Topics in Heterocyclic Chemistry. Eds. B.U.W. Maes, J. Cossy, S. Polanc. Heidelberg, New York, Dordrecht, London: Springer Cham. 2015, 39, 1-5. doi: 10.1007/7081_2014_130
  4. Besson T., Thiéry V. Top. Heterocycl. Chem. 2006, 1, 59-78. doi: 10.1007/7081_008
  5. Mancuso R., Gabriele B. Molecules. 2014, 19, 15687-15719. doi: 10.3390/molecules191015687
  6. Mishra A., Ma C.-Q., Bäuerle P. Chem. Rev. 2009, 109, 1141-1276. doi: 10.1021/cr8004229
  7. Klingstedt T., Nilsson K.P.R. Biochem. Soc. Trans. 2012, 40, 704-710. doi: 10.1042/BST20120009
  8. Cheylan S., Fraleoni-Morgera A., Puigdollers J., Voz C., Setti L., Alcubilla R., Badenes G., Costa-Bizzarri P., Lanzi M. Thin Solid Films. 2006, 497, 16-19. doi: 10.1016/j.tsf.2005.09.177
  9. Ong B.S., Wu Y., Li Y., Liu P., Pan H. Chem. Eur. J. 2008, 14, 4766-4778. doi: 10.1002/chem.200701717
  10. Abd-El-Aziz A.S., Afifi T.H. Dyes Pigm. 2006, 70, 8-17. doi: 10.1016/j.dyepig.2005.03.004
  11. Nassar H.S. Int. J. Text. Sci. 2015, 4, 102-112. doi: 10.5923/j.textile.20150405.02
  12. Wu, L.-H., Wang Y.-C., Hsu C.-S. Liq. Cryst. 2001, 27, 1503-1513. doi: 10.1080/026782900750018672
  13. Mishra R., Jha K.K., Kumar S., Tomer I. Pharma Chem. 2011, 3, 38-54.
  14. Chaudhary A., Jha K.K., Kumar S. J. Adv. Sci. Res. 2012, 3, 3-10.
  15. Mabkhot Y.N., Kheder N.A., Barakat A., Choudhary M.I., Yousufe S., Frey W. RSC Adv. 2016, 6, 63724-63729. doi: 10.1039/C6RA09883E
  16. Mishra R., Sharma P.K., Verma P., Mishra I. Eur. Chem. Bull. 2016, 5, 399-407. doi: 10.17628/ECB.2016.5.399
  17. Wilson R., Kumar P., Parashar V., Vilchèze C., Veyron-Churlet R., Freundlich J.S., Barnes S.W., Walker J.R., Szymonifka M.J., Marchiano E., Shenai S., Colangeli R., Jacobs W.R., Jr, Neiditch M.B., Kremer L., Alland D. Nat. Chem. Biol. 2013, 9, 499-509. doi: 10.1038/nchembio.1277
  18. Lu X., Wan B., Franzblau S.G., You Q. Eur. J. Med. Chem. 2011, 46, 3551-3563. doi: 10.1016/j.ejmech.2011.05.018
  19. Puterová Z., Krutošíková A., Végh D. Nova Biotechnol. 2009, 9, 167-173. doi: 10.36547/nbc.1274
  20. Briel D., Rybak A., Kronbach C., Unverferth K. Eur. J. Med. Chem. 2010, 45, 69-77. doi: 10.1016/j.ejmech.2009.09.025
  21. Sperry J.B., Wright D.L. Curr. Opin. Drug Discov. Dev. 2005, 8, 723-740.
  22. Corral C., Lissavetzky J., Manzanares I., Darias V., Exposito-Orta M.A., Martin Conde J.A., Sanchez-Mateo C. Bioorg. Med. Chem. 1999, 7, 1349-1359. doi: 10.1016/S0968-0896(99)00070-X
  23. Yang S.-M., Fang J.-M. Tetrahedron. 2007, 63, 1421-1428. doi: 10.1016/j.tet.2006.11.080
  24. Yang S.-M., Nandy S.K., Selvakumar A.R., Fang J.-M. Org. Lett. 2000, 2, 3719-3721. doi: 10.1021/ol006628w
  25. Schatz J., Brendgen T., Schühle D. Compr. Heterocycl. Chem. III. 2008, 3, 931-974.
  26. Liu M., Zeng M.-T., Xu W., Chang C.-z., Liu X., Zhu H., Li Y.-s., Dong Z.B. J. Chem. Res. 2017, 41, 165-167. doi: 10.3184/174751917X14878812592733
  27. Ma C., Wu A., Wu Y., Ren X., Cheng M. Archiv Pharm. (Weinheim, Germany). 2013, 346, 891-900. doi: 10.1002/ardp.201300276
  28. Sulthana M.T., Alagarsamy V., Chitra K. Med. Chem. (Sharjah, United Arab Emirates). 2021, 17, 352-368. doi: 10.2174/1573406416666200817153033
  29. Lei X., Wang Y., Fan E., Sun Z. Org. Lett. 2019, 21, 1484-1487. doi: 10.1021/acs.orglett.9b00275
  30. Padilla-Martinez I.I., Gonzalez-Encarnacion J.M., Garcia-Baez E.V., Cruz A., Ramos-Organillo A.A. Molecules. 2019, 24, 3391. doi: 10.3390/molecules24183391
  31. Sabolova D., Kristian P., Kozurkova M. J. Appl. Toxicol. 2018, 38, 1377-1387. doi: 10.1002/jat.3622
  32. Siddiqui N., Alam M.S., Sahu M., Naim M.J., Yar M.S., Alam O. Bioorg. Chem. 2017, 71, 230-243. doi: 10.1016/j.bioorg.2017.02.009
  33. Tiratsuyan S.G., Hovhannisyan A.A., Karapetyan A.V., Gomktsyan T.A., Yengoyan A.P. Russ. J. Plant Physiol. 2016, 63, 656-662. doi: 10.1134/S1021443716050125
  34. Bandi N., Veerachamy A., Chitra K. Drug Res. 2020, 70, 348-355. doi: 10.1055/a-0991-7617
  35. Boddapati S.N.M., Kurmarayuni C.M., Mutchu B.R., Tamminana R., Bollikolla H.B. Org. Biomol. Chem. 2018, 16, 6889-6894. doi: 10.1039/c8ob02018c
  36. Cannito A., Perrissin M., Luu Duc C., Huguet F., Gaultier C., Narcisse G. Eur. J. Med. Chem. 1990, 25, 635-639. doi: 10.1016/0223-5234(90)90128-P
  37. Katritzky A.R., Witek R.M., Rodriguez-Garcia V., Mohapatra P.P., Rogers J.W., Cusido J., Abdel-Fattah A.A.A., Steel P.J. J. Org. Chem. 2005, 70, 7866-7881. doi: 10.1021/jo050670t
  38. Biswas A., Mondal H., Maji M.S. J. Heterocycl. Chem. 2020, 57, 3818-3844. doi: 10.1002/jhet.4119
  39. Maiti R., Xu J., Yan J.-L., Mondal B., Yang X., Chai H., Hao L., Jin Z., Chi Y.R. Org. Chem. Front. 2021, 8, 743-747. doi: 10.1039/d0qo01380c
  40. Koronkiewicz M., Romiszewska A., Chilmonczyk Z., Kazimierczuk Z. Med. Chem. 2015, 11, 364-372. doi: 10.2174/1573406410666141203124329
  41. Pucko E., Matyja E., Koronkiewicz M., Ostrowski R.P., Kazimierczuk Z. Anticancer Res. 2018, 38, 2691-2705. doi: 10.21873/anticanres.12511
  42. Lambert W.T., Goldsmith M.E., Sparks T.C. Pest Manage. Sci. 2017, 73, 743-751. doi: 10.1002/ps.4353
  43. Narendhar B., Chitra K., Alagarsamy V. Pharm. Chem. J. 2021, 55, 54-59. doi: 10.1007/s11094-021-02371-7
  44. Narendhar B., Chitra K., Alagarsamy V. Int. J. Res. Pharm. Sci. 2019, 10, 2186-2193. doi: 10.26452/ijrps.v10i3.1414
  45. Uckun F.M., Tibbles H.E., Venkatachalam T.K., Erbeck D. Arzneim.-Forsch. 2007, 57, 483-496. doi: 10.1055/s-0031-1296636
  46. Клыба Л.В., Недоля Н.А., Санжеева Е.Р., Тарасова О.А. ЖОрХ. 2019, 55, 620-627.
  47. Klyba L.V., Nedolya N.A. Sanzheeva E.R., Tarasova O.A. Russ. J. Org. Chem. 2019, 55, 518-524. doi: 10.1134/S1070428019040171
  48. Недоля Н.А., Тарасова О.А., Клыба Л.В., Дмитриева Г.В., Трофимов Б.А. Сборник тезисов III Международной конференции "Химия гетероциклических соединений", посвященной 95-летию со дня рождения профессора Алексея Николаевича Коста (18-21 октября 2010 г.), Москва, 2010, 146.
  49. Клыба Л.В., Недоля Н.А., Шляхтина Н.И., Жанчипова Е.Р. ЖОрХ. 2005, 41, 1576-1582.
  50. Klyba L.V., Nedolya N.A., Shlyakhtina N.I., Zhanchipova E.R. Russ. J. Org. Chem. 2005, 41, 1544-1550. doi: 10.1007/s11178-005-0380-y
  51. Клыба Л.В., Недоля Н.А., Тарасова О.А., Жанчипова Е.Р., Волостных О.Г. ЖОрХ. 2010, 46, 224-231.
  52. Klyba L.V., Nedolya N.A., Tarasova O.A., Zhanchipova E.R., Volostnykh O.G. Russ. J. Org. Chem. 2010, 46, 218-225. doi: 10.1134/S107042801002013

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