A new method for regioselective nucleophilic substitution at one of the three possible reaction centers of seleniranium cation, generated from 2-(bromomethyl)-1,3-thiaselenole, with mono- and bicyclic nitrogen-containing heteroaromatic thiols was developed. The reaction was directed at the carbon atom attached to sulfur atom of the intermediate seleniranium cation and was accompanied by rearrangement with ring expansion to afford in high yields new (2,3-dihydro-1,4-thiaselenin-2-yl)sulfanyl-substituted pharmacophoric heterocycles with one to four nitrogen atoms. The reaction of 2-(bromomethyl)-1,3-thiaselenole and quinoxaline-2,3-dithiol provided the corresponding 2,3-bis[(2,3-dihydro-1,4-thiaselenin-2-yl)sulfanyl] derivative. In the case of 5-methyl-1,3,4-thiadiazole-2-thiol, the reaction in MeCN led to 2-methyl-5-{[(1,3-thiaselenol-2-yl)methyl]sulfanyl}-1,3,4-thiadiazole at the expense of rearrangement of the intermediate (2,3-dihydro-1,4-thiaselenin-2-yl)sulfanyl derivative in a form of hydrobromide salt with the ring contraction proceeding via seleniranium cation. The synthesized novel sulfur- and selenium-containing functionalized unsaturated heterocycles can be considered as potential scaffolds for medicinal chemistry.
Similar content being viewed by others
References
(a) Singh, F. V.; Wirth, T. In Physical Sciences Reviews; Giamberini, M.; Jastrzab, R.; Liou, J. J.; Luque, R.; Nawab, Y.; Saha, B.; Tylkowski, B.; Xu, C.-P.; Cerruti, P.; Ambrogi, V.; Marturano, V.; Gulaczyk, I., Eds.; Walter de Gruyter: Berlin, Boston, 2018, Vol. 4, p. 20170131. (b) Chivers, T.; Laitinen, R. S. In Physical Sciences Reviews; Giamberini, M.; Jastrzab, R.; Liou, J. J.; Luque, R.; Nawab, Y.; Saha, B.; Tylkowski, B.; Xu, C.-P.; Cerruti, P.; Ambrogi, V.; Marturano, V.; Gulaczyk, I., Eds.; Walter de Gruyter: Berlin, Boston, 2018, Vol. 3, p. 20180060. (c) Lenardão, E. J.; Santi, C.; Sancineto, L. New Frontiers in Organoselenium Compounds; Springer: Heidelberg, 2018. (d) Santi, C.; Santoro, S. In Organoselenium Chemistry: Synthesis and Reactions; Wirth, T., Ed.; Wiley-VCH: Weinheim, 2011, p. 1. (e) Freudendahl, D. M.; Wirth, T. In Selenium and Tellurium Chemistry. From Small Molecules to Biomolecules and Materials; Woollins, J. D.; Laitinen, R. S., Eds.; Springer-Verlag: Heidelberg, 2011, p. 41. (f) Dutton, J. L.; Ragogna, P. J. In Selenium and Tellurium Chemistry. From Small Molecules to Biomolecules and Materials; Woollins, J. D.; Laitinen, R. S., Eds.; Springer-Verlag: Heidelberg, 2011, p. 179. (g) Browne, D. M.; Niyomura, O.; Wirth, T. Org. Lett.2007, 9, 3169. (h) Denmark, S. E.; Collins, W. R.; Cullen, M. D. J. Am. Chem. Soc.2009, 131, 3490. (i) Gabriele, E.; Singh, F. V.; Freudendahl, D. M.; Wirth, T. Tetrahedron2012, 68, 10573. (j) Freudendahl, D. M.; Iwaoka, M.; Wirth, T. Eur. J. Org. Chem.2010, 3934. (k) Ścianowski, J.; Rafiński, Z. In Organoselenium Chemistry: Between Synthesis and Biochemistry; Santi, C., Ed.; Bentham Science Publishers: Sharjah, 2014, p. 8. (l) Cox, M.; Wirth, T. Phosphorus, Sulfur Silicon Relat. Elem.2005, 180, 659.
(a) Potapov, V. A.; Amosova, S. V.; Belozerova, O. V.; Albanov, A. I.; Yarosh, O. G.; Voronkov, M. G. Chem. Heterocycl. Compd.2003, 39, 549. [Khim. Geterotsikl. Soedin.2003, 633.] (b) Potapov, V. A.; Amosova, S. V. Russ. J. Org. Chem.2003, 39, 1373. [Zh. Org. Khim.2003, 39, 1449.]
(a) Potapov, V. A.; Musalov, M. V.; Musalova, M. V.; Amosova, S. V. Curr. Org. Chem.2016, 20, 136. (b) Abakumov, G. A.; Piskunov, A. V.; Cherkasov, V. K.; Fedushkin, I. L.; Ananikov, V. P.; Eremin, D. B.; Gordeev, E. G.; Beletskaya, I. P.; Averin, A. D.; Bochkarev, M. N.; Trifonov, A. A.; Dzhemilev, U. M.; Dyakonov, V. A.; Egorov, M. P.; Vereshchagin, A. N.; Syroeshkin, M. A.; Jouikov, V. V.; Muzafarov, A. M.; Anisimov, A. A.; Arzumanyan, A. V.; Kononevich, Yu. N.; Temnikov, M. N.; Synyashin, O. G.; Budnikova, Yu. H.; Burilov, A. R.; Karasik, A. A.; Mironov, V. F.; Storozhenko, P. A.; Shcherbakova, G. I.; Trofimov, B. A.; Amosova, S. V.; Gusarova, N. K.; Potapov, V. A.; Shur, V. B.; Burlakov, V. V.; Bogdanov, V. S.; Andreev, M. V. Russ. Chem. Rev.2018, 87, 393. [Usp. Khim.2018, 87, 393.]
Amosova, S. V.; Penzik, M. V.; Albanov, A. I.; Potapov, V. A. Tetrahedron Lett.2009, 50, 306.
(a) Amosova, S. V.; Novokshonova, I. A.; Penzik, M. V.; Filippov, A. S.; Albanov, A. I.; Potapov, V. A. Tetrahedron Lett.2017, 58, 4381. (b) Amosova, S. V.; Penzik, M. V.; Potapov, V. A.; Filippov, A. S.; Shagun, V. A.; Albanov, A. I.; Borodina, T. N.; Smirnov, V. I. Synlett2016, 1653.
(a) Amosova, S. V.; Filippov, A. S.; Potapov, V. A.; Penzik, M. V.; Makhaeva, N. A.; Albanov, A. I. Synthesis2019, 1832. (b) Amosova, S. V.; Filippov, A. S.; Makhaeva, N. A.; Albanov, A. I.; Potapov, V. A. New J. Chem.2019, 43, 11189. (c) Amosova, S. V.; Filippov, A. S.; Potapov, V. A.; Makhaeva, N. A.; Albanov, A. I. Russ. J. Org. Chem.2018, 54, 1697. [Zh. Org. Khim.2018, 54, 1682.]
Amosova, S. V.; Penzik, M. V.; Rykunova, Yu. I.; Potapov, V. А.; Albanov, А. I. Russ. J. Org. Chem.2017, 53, 1691. [Zh. Org. Khim.2017, 53, 1655.]
(a) Lukevits, E. Chem. Heterocycl. Compd.1995, 31, 639. [Khim. Geterotsikl. Soedin. 1995, 723.] (b) Tolba, M. S.; Kamal El-Dean, A. M.; Ahmed, M.; Hassanien, R. J. Chin. Chem. Soc.2019, 66, 548. b Jampilek, J. Curr. Med. Chem.2014, 21, 4347. c Azev, Yu. A.; Koptyaeva, O. S.; Tsmokalyuk, A. N.; Pospelova, T. A.; Gerasimova, N. A.; Evstigneeva, N. P.; Zil'berberg, N. V.; Kungurov, N. V.; Chupakhin, O. N. Chem. Nat. Compd.2019, 55, 513. [Khim. Prir. Soedin. 2019, 441.]
(a) Singh, R.; Chouhan, A. World J. Pharm. Pharm. Sci.2014, 3, 574. (b) Arunachalam, S.; Gowrishankar, N. L.; Krishnan, A.; Akhileswaran, A.; Tindu, K. D. World J. Pharm. Pharm. Sci.2017, 6, 436. (c) Patil, S. B. Int. J. Pharm. Sci. Res.2018, 9, 44. (d) Jain, K. S.; Arya, N.; Inamdar, N. N.; Auti, P. B.; Unawane, S. A.; Puranik, H. H.; Sanap, M. S.; Inamke, A. D.; Mahale, V. J.; Prajapati, C. S.; Shishoo, C. J. Curr. Top. Med. Chem.2016, 16, 3133.
(a) Solomon, V. R.; Lee, H. Curr. Med. Chem.2011, 18, 1488. (b) Jhanwar, D.; Sharma, J. Int. J. Pharm. Res. Bio-Sci.2015, 4, 130.
(a) Pinheiro, A. C.; Mendonça Nogueira, T. C.; de Souza, M. V. N. Anti-Cancer Agents Med. Chem.2016, 16, 1339. (b) Irfan, A.; Sabeeh, I.; Umer, M.; Naqvi, A. Z.; Fatima, H.; Yousaf, S.; Fatima, Z. World J. Pharm. Res.2017, 6, 47. (c) El Newahie, A. M. S.; Nissan, Y. M.; Ismail, N. S. M.; El Ella, D. A. A; Khojah, S. M; Abouzid, K. A. M. Molecules2019, 24, 1175/1.
(a) Khalilullah, H.; Khan, M. U.; Mahmood, D.; Akhtar, J.; Osman, G. Int. J. Pharm. Pharm. Sci.2014, 6, 8. (b) Kalidhar, U; Kaur, A. Res. J. Pharm., Biol. Chem. Sci.2011, 2, 1091. (c) Raj, V.; Rai, A.; Saha, S. Anti-Cancer Agents Med. Chem.2017, 17, 500.
(a) Ostrovskii, V. A.; Trifonov, R. E.; Popova, E. A. Russ. Chem. Bull., Int. Ed.2012, 61, 768. [Izv. Akad. Nauk, Ser. Khim.2012, 765]. (b) Kaushik, N.; Kumar, N.; Kumar, A.; Singh, U. K. Immunol. Endocr. Metab. Agents Med. Chem.2018, 18, 3.
Bildziukevich, U.; Rárová, L.; Šaman, D.; Wimmer, Z. Eur. J. Med. Chem.2018, 145, 41.
(a) Joshi, S. D.; Jangade, N. M.; Dixit, S. R.; Joshi, A. S.; Kulkarni, V. H. Indo Am. J. Pharm. Res.2016, 6, 5033. (b) Atwell, G. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem.1989, 32, 396.
Singh, R.; Chouhan, A. World J. Pharm. Pharm. Sci.2014, 3, 574.
(a) Myznikov, L. V.; Hrabalek, A.; Koldobskii, G. I. Chem. Heterocycl. Compd.2007, 43, 1. [Khim. Geterotsikl. Soedin. 2007, 3.] (b) Gao, C.; Chang, L.; Xu, Z.; Yan, X.-F.; Ding, C.; Zhao, F.; Wu, X.; Feng, L.-S. Eur. J. Med. Chem.2019, 163, 404.
(a) Mugesh, G.; du Mont, W.-W.; Sies, H. Chem. Rev.2001, 101, 2125.(b) Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Chem. Rev.2004, 104, 6255. (c) Soriano-Garcia, M. Curr. Med. Chem.2004, 11, 1657. (d) Nogueira, C. W.; Rocha, J. B. T. Arch. Toxicol.2011, 85, 1313. (e) Sanmartín, C.; Plano, D.; Sharma, A. K.; Palop, J. A. Int. J. Mol. Sci.2012, 13, 9649. (f) May, S. W. In Topics in Medicinal Chemistry; Schwarz, J., Ed.; Springer: Cham, 2016, Vol. 17, p. 87. (g) Banerjee, B.; Koketsu, M. Coord. Chem. Rev.2017, 339, 104. (h) Elsherbini, M.; Hamama, W. S.; Zoorob, H. H. Coord. Chem. Rev.2016, 312, 149. (i) Ninomiya, M.; Garud, D. R.; Koketsu, M. Coord. Chem. Rev.2011, 255, 2968. (j) Naithani, R. Mini-Rev. Med. Chem.2008, 8, 657. (k) Sancineto, L.; Mariotti, A.; Bagnoli, L.; Marini, F.; Desantis, J.; Iraci, N.; Santi, C.; Pannecouque, C.; Tabarrini, O. J. Med. Chem.2015, 58, 9601. (l) Bartolini, D.; Sancineto, L.; de Bem, A. F.; Tew, K. D.; Santi, C.; Radi, R.; Toquato, P.; Galli, F. In Advances in Cancer Research; Tew, K. D.; Galli, F., Eds.; Elsevier: New York, 2017, Vol. 136, p. 259. (m) Wirth, T. Angew. Chem., Int. Ed.2015, 54, 10074. (n) Fonseca, S. F.; Lima, D. B.; Alves, D.; Jacob, R. G.; Perin, G.; Lenardão, E. J.; Savegnago, L. New J. Chem.2015, 39, 3043. (o) Iwaoka, M.; Arai, K. Curr. Chem. Biol.2013, 7, 2.
(a) Saito, I.; Asano, T.; Sano, K.; Takakura, K.; Abe, H.; Yoshimoto, T.; Kikuchi, H.; Ishibashi, S. Neurosurgery1998, 42, 269. (b) Yamaguchi, T.; Sano, K.; Takakura, K.; Saito, I.; Shinohara, Y.; Asano, T.; Yasuhara, H. Stroke1998, 29, 12.
Duddeck, H. Prog. Nucl. Magn. Reson. Spectrosc.1995, 27, 1.
PASS, Version 2.0; Way2Drug: Moscow, 2011.
The work was performed using the material and technical base of the Baikal Analytical Center for Collective Use, Siberian Branch of the Russian Academy of Sciences.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(2), 226–232
Electronic supplementary material
ESM 1
(PDF 1906 kb)
Rights and permissions
About this article
Cite this article
Amosova, S.V., Martynov, A.V., Albanov, A.I. et al. Synthesis of novel (2,3-dihydro-1,4-thiaselenin-2-yl)sulfanyl-substituted pharmacophoric nitrogen heterocycles based on 2-(bromomethyl)-1,3-thiaselenole. Chem Heterocycl Comp 56, 226–232 (2020). https://doi.org/10.1007/s10593-020-02648-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-020-02648-x