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YENİ S-İKAME EDİLMİŞ BIS-1,2,4-TRİAZOLLERİN SENTEZİ VE FİZİKSEL KİMYASAL ÖZELLİKLERİ

Year 2021, , 150 - 161, 01.09.2021
https://doi.org/10.52794/hujpharm.973420

Abstract

Özet. Çalışmanın amacı, bir molekülde iki 1,2,4-triazol sistemini birleştirme yöntemini, daha önce keşfedilmemiş 1,2,4-triazolün S-türevlerini elde etmek için tiyol grubunun alkilasyon reaksiyonunu ve gaz kromatografisi-kütle spektrometrisi kullanılarak sert iyonizasyon altındaki maddelerin parçalanma yolu. Sentezlenen bileşiklerin yapıları element analizi, 1H ve 13C NMR spektroskopisi ve GC-MS analizi ile doğrulandı. S-alkil tortuları için karakteristik sinyaller, alifatik bileşikler için tipik olan bölgede gözlendi. Moleküllerin parçalanması, radikallerin kademeli olarak bölünmesi ve ikinci 1,2,4-triazol heterosiklinin açılması ile temsil edildi.

References

  • 1. 1. Orlewska, C.; Pancechowska-Ksepko, D.; Foks, H.; Zwolska, Z.; Augustynowicz-Kopec, E. Reactivity of N 1-Dithioester Substituted Pyridinand Pyrazincarboxamidrazones. Phosphorus, Sulfur, and Silicon and the Related Elements, 2006, 181(4), pp. 737–744. https://doi.org/10.1080/10426500500270065
  • 2. Pellizzari, G.; Gazz Chim Ital, 1911, no. 41, pp. 93.
  • 3. Ji Ram, V.; Sethi, A.; Nath, M.; Pratap, R. Five-Membered Heterocycles. The Chemistry of Heterocycles, 2019, pp. 365. https://doi.org/10.1016/b978-0-08-101033-4.00005-x
  • 4. Ueda, S.; Nagasawa, H. Facile synthesis of 1,2,4-triazoles via a copper-catalyzed tandem addition−oxidative cyclization. Journal of the American Chemical Society, 2009, 131(42), pp. 15080-15081. DOI: https://doi.org/10.1021/ja905056z
  • 5. Huang, H.; Guo, W.; Wu, W.; Li, C.-J.; Jiang, H. Copper-catalyzed oxidative C(sp3)–H functionalization for facile synthesis of 1,2,4-triazoles and 1,3,5-triazines from amidines. Organic Letters, 2015, 17(12), pp. 2894-2897. DOI: https://doi.org/10.1021/acs.orglett.5b00995
  • 6. Castanedo, G. M.; Seng, P. S.; Blaquiere, N.; Trapp, S.; Staben, S. T. Rapid synthesis of 1,3,5-substituted 1,2,4-triazoles from carboxylic acids, amidines, and hydrazines. The Journal of Organic Chemistry, 2011, 76(4), pp. 1177-1179. DOI: https://doi.org/10.1021/jo1023393
  • 7. Vidavalur, S.; Nakka, M.; Tadikonda, R.; Rayavarapu, S.; Sarakula, P. A Simple and efficient synthesis of 3,4,5-trisubstituted/n-fused 1,2,4-triazoles via ceric ammonium nitrate catalyzed oxidative cyclization of amidrazones with aldehydes using polyethylene glycol as a recyclable reaction medium. Synthesis, 2014, 47(04), pp. 517-525. DOI: https://doi.org/10.1055/s-0034-1378909
  • 8. Minozzi, C.; Caron, A.; Grenier-Petel, J.; Santandrea, J.; Collins, S. Heteroleptic copper(I)-based complexes for photocatalysis: combinatorial assembly, discovery, and optimization. Angewandte Chemie International Edition, 2018, 57(19), pp. 5477-5481. DOI: 10.1002/anie.201800144
  • 9. Arnold, F. Directed evolution: bringing new chemistry to life. Angewandte Chemie International Edition, 2017, 57(16), pp. 4143-4148. DOI: 10.1002/anie.201708408
  • 10. Klimešová, V.; Zahajská, L.; Waisser, K.; Kaustová, J.; Möllmann, U. Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. Il Farmaco, 2004, 59(4), pp. 279-288. DOI: 10.1016/j.farmac.2004.01.006
  • 11. Kapro ´n, B.; Łuszczki, J.J.; Płazi ´nska, A.; Siwek, A.; Karcz, T.; Grybo´s, A.; Nowak, G.; Makuch-Kocka, A.; Walczak, K.; Langner, E. Development of the 1,2,4-triazole-based anticonvulsant drug candidates acting on the voltage-gated sodium channels. Insights from in-vivo, in-vitro, and in-silico studies. Eur. J. Pharm. Sci., 2019, 129, pp. 42–57. https://doi.org/10.1016/j.ejps.2018.12.018
  • 12. Timur, ˙I.; Kocyigit, Ü.M.; Dastan, T.; Sandal, S.; Ceribası, A.O.; Taslimi, P.; Gulcin, ˙I.; Koparir, M.; Karatepe, M.; Çiftçi, M.J. In vitro cytotoxic and in vivo antitumoral activities of some aminomethyl derivatives of 2,4-dihydro-3H-1,2,4-triazole-3-thiones—Evaluation of their acetylcholinesterase and carbonic anhydrase enzymes inhibition profiles. Biochem. Mol. Toxicol, 2019, 33, pp. 22239–22250 https://doi.org/10.1002/jbt.22239
  • 13. Mishra, C.B.; Mongre, R.K.; Kumari, S.; Jeong, D.K.; Tiwari, M. Novel Triazole-Piperazine Hybrid Molecules Induce Apoptosis via Activation of the Mitochondrial Pathway and Exhibit Antitumor Efficacy in Osteosarcoma Xenograft Nude Mice Model. ACS Chem. Biol, 2017, 17, pp. 753–768. https://doi.org/10.1021/acschembio.6b01007
  • 14. Mermer, A.; Demirbaş, N.; Şirin, Y.; Uslu, H.; Özdemir, Z.; Demirbaş, A. Conventional and microwave prompted synthesis, antioxidant, anticholinesterase activity screening and molecular docking studies of new quinolone-triazole hybrids. Bioorganic Chemistry, 2018, 78, pp. 236-248. DOI: 10.1016/j.bioorg.2018.03.017

Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles

Year 2021, , 150 - 161, 01.09.2021
https://doi.org/10.52794/hujpharm.973420

Abstract

The aim of the work was to describe the method of combining two 1,2,4-triazole systems in a molecule, the alkylation reaction of the thiol group to obtain the previ- ously undiscovered S-derivatives of 1,2,4-triazole and the fragmentation pathway of the substances under hard ionization using gas chromatography-mass spectrom- etry. The structures of the synthesized compounds were confirmed by elemental analysis, 1H and 13C NMR spectroscopy and GC-MS analysis. The characteristic signals for S-alkyl residues were observed in the region typical for aliphatic com- pounds. The fragmentation of molecules was represented by the gradual cleavage of radicals and the opening of the second 1,2,4-triazole heterocycle.

References

  • 1. 1. Orlewska, C.; Pancechowska-Ksepko, D.; Foks, H.; Zwolska, Z.; Augustynowicz-Kopec, E. Reactivity of N 1-Dithioester Substituted Pyridinand Pyrazincarboxamidrazones. Phosphorus, Sulfur, and Silicon and the Related Elements, 2006, 181(4), pp. 737–744. https://doi.org/10.1080/10426500500270065
  • 2. Pellizzari, G.; Gazz Chim Ital, 1911, no. 41, pp. 93.
  • 3. Ji Ram, V.; Sethi, A.; Nath, M.; Pratap, R. Five-Membered Heterocycles. The Chemistry of Heterocycles, 2019, pp. 365. https://doi.org/10.1016/b978-0-08-101033-4.00005-x
  • 4. Ueda, S.; Nagasawa, H. Facile synthesis of 1,2,4-triazoles via a copper-catalyzed tandem addition−oxidative cyclization. Journal of the American Chemical Society, 2009, 131(42), pp. 15080-15081. DOI: https://doi.org/10.1021/ja905056z
  • 5. Huang, H.; Guo, W.; Wu, W.; Li, C.-J.; Jiang, H. Copper-catalyzed oxidative C(sp3)–H functionalization for facile synthesis of 1,2,4-triazoles and 1,3,5-triazines from amidines. Organic Letters, 2015, 17(12), pp. 2894-2897. DOI: https://doi.org/10.1021/acs.orglett.5b00995
  • 6. Castanedo, G. M.; Seng, P. S.; Blaquiere, N.; Trapp, S.; Staben, S. T. Rapid synthesis of 1,3,5-substituted 1,2,4-triazoles from carboxylic acids, amidines, and hydrazines. The Journal of Organic Chemistry, 2011, 76(4), pp. 1177-1179. DOI: https://doi.org/10.1021/jo1023393
  • 7. Vidavalur, S.; Nakka, M.; Tadikonda, R.; Rayavarapu, S.; Sarakula, P. A Simple and efficient synthesis of 3,4,5-trisubstituted/n-fused 1,2,4-triazoles via ceric ammonium nitrate catalyzed oxidative cyclization of amidrazones with aldehydes using polyethylene glycol as a recyclable reaction medium. Synthesis, 2014, 47(04), pp. 517-525. DOI: https://doi.org/10.1055/s-0034-1378909
  • 8. Minozzi, C.; Caron, A.; Grenier-Petel, J.; Santandrea, J.; Collins, S. Heteroleptic copper(I)-based complexes for photocatalysis: combinatorial assembly, discovery, and optimization. Angewandte Chemie International Edition, 2018, 57(19), pp. 5477-5481. DOI: 10.1002/anie.201800144
  • 9. Arnold, F. Directed evolution: bringing new chemistry to life. Angewandte Chemie International Edition, 2017, 57(16), pp. 4143-4148. DOI: 10.1002/anie.201708408
  • 10. Klimešová, V.; Zahajská, L.; Waisser, K.; Kaustová, J.; Möllmann, U. Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. Il Farmaco, 2004, 59(4), pp. 279-288. DOI: 10.1016/j.farmac.2004.01.006
  • 11. Kapro ´n, B.; Łuszczki, J.J.; Płazi ´nska, A.; Siwek, A.; Karcz, T.; Grybo´s, A.; Nowak, G.; Makuch-Kocka, A.; Walczak, K.; Langner, E. Development of the 1,2,4-triazole-based anticonvulsant drug candidates acting on the voltage-gated sodium channels. Insights from in-vivo, in-vitro, and in-silico studies. Eur. J. Pharm. Sci., 2019, 129, pp. 42–57. https://doi.org/10.1016/j.ejps.2018.12.018
  • 12. Timur, ˙I.; Kocyigit, Ü.M.; Dastan, T.; Sandal, S.; Ceribası, A.O.; Taslimi, P.; Gulcin, ˙I.; Koparir, M.; Karatepe, M.; Çiftçi, M.J. In vitro cytotoxic and in vivo antitumoral activities of some aminomethyl derivatives of 2,4-dihydro-3H-1,2,4-triazole-3-thiones—Evaluation of their acetylcholinesterase and carbonic anhydrase enzymes inhibition profiles. Biochem. Mol. Toxicol, 2019, 33, pp. 22239–22250 https://doi.org/10.1002/jbt.22239
  • 13. Mishra, C.B.; Mongre, R.K.; Kumari, S.; Jeong, D.K.; Tiwari, M. Novel Triazole-Piperazine Hybrid Molecules Induce Apoptosis via Activation of the Mitochondrial Pathway and Exhibit Antitumor Efficacy in Osteosarcoma Xenograft Nude Mice Model. ACS Chem. Biol, 2017, 17, pp. 753–768. https://doi.org/10.1021/acschembio.6b01007
  • 14. Mermer, A.; Demirbaş, N.; Şirin, Y.; Uslu, H.; Özdemir, Z.; Demirbaş, A. Conventional and microwave prompted synthesis, antioxidant, anticholinesterase activity screening and molecular docking studies of new quinolone-triazole hybrids. Bioorganic Chemistry, 2018, 78, pp. 236-248. DOI: 10.1016/j.bioorg.2018.03.017
There are 14 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Research Articles
Authors

Yevhen Karpun

Publication Date September 1, 2021
Acceptance Date October 4, 2021
Published in Issue Year 2021

Cite

Vancouver Karpun Y. Synthesis, Structure and Properties of Novel S-Substituted BIS-1,2,4-Triazoles. HUJPHARM. 2021;41(3):150-61.