Synthesis of novel triazoles bearing 1,2,4-oxadiazole and phenylsulfonyl groups by 1,3-dipolar cycloaddition of some organic azides and their biological activities

1,3-Dipolar cycloaddition of 5-azidomethyl-3-p-substituted phenyl-1,2,4-oxadiazoles to phenyl vinyl sulfone and bismaleimide gives rise straightforwardly to 1-((3-(p-substituted) phenyl-1,2,4-oxadiazol-5-yl)methyl)-4-(phenylsul\-fonyl)-4,5-dihydro-1H-1,2,3-triazoles and bisdihydropyrrolo[3,4-d][1,2,3]triazole-4,6(3aH,5H)-diones. The structures of the new cycloadducts were elucidated by means of IR, NMR (1H, 13C, 2D), mass spectra, and physical characteristics (mp and Rf values). In addition, anticancer activities of the cycloadducts against MCF-7 cells were also investigated.

Synthesis of novel triazoles bearing 1,2,4-oxadiazole and phenylsulfonyl groups by 1,3-dipolar cycloaddition of some organic azides and their biological activities

1,3-Dipolar cycloaddition of 5-azidomethyl-3-p-substituted phenyl-1,2,4-oxadiazoles to phenyl vinyl sulfone and bismaleimide gives rise straightforwardly to 1-((3-(p-substituted) phenyl-1,2,4-oxadiazol-5-yl)methyl)-4-(phenylsul\-fonyl)-4,5-dihydro-1H-1,2,3-triazoles and bisdihydropyrrolo[3,4-d][1,2,3]triazole-4,6(3aH,5H)-diones. The structures of the new cycloadducts were elucidated by means of IR, NMR (1H, 13C, 2D), mass spectra, and physical characteristics (mp and Rf values). In addition, anticancer activities of the cycloadducts against MCF-7 cells were also investigated.

___

  • Ding, S.; Jia, G.; Sun, J. Angew. Chem. Int. Ed. 2014, 53, 1877–1880.
  • Gao, J.; Zhang, X.; Xu, S.; Tan, F.; Li, X.; Zhang, Y.; Qu, Z.; Quan, X.; Liu, J. Chem. Eur. J. 2014, 20, 1957–1963.
  • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596–2599.
  • Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin,V. V. J. Am. Chem.
  • Soc. 2005, 127, 210–216.
  • White, J. D.; Osborn, M. F.; Moghaddam, A. D.; Guzman, L. E.; Haley, M. M.; DeRose, V. J. J. Am. Chem.
  • Soc. 2013, 135, 11680–11683.
  • Fu, T-H.; Li, Y.; Thaker, H. D.; Scott, R. W.; Tew, G. N. ACS Med. Chem. Lett. 2013, 4, 841–845.
  • Kushwaha, D.; Tiwari, V. K. J. Org. Chem. 2013, 78, 8184–8190.
  • Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905–4979.
  • Li, X.; Tu, Z.; Li, H.; Liu, C.; Li, Z.; Sun, Q.; Yao, Y.; Liu, J.; Jiang, S. ACS Med. Chem. Lett. 2013, 4, 132–136.
  • Suzuki, T.; Ota, Y.; Ri, M.; Bando, M.; Gotoh, A.; Itoh, Y.; Tsumoto, H.; Tatum, P. R.; Mizukami, T.; Nakagawa,
  • H.; et al. J. Med. Chem. 2012, 55, 9562–9575.
  • R. M.; De Oliveira, C. F.; Antunes, M. V.; Medeiros, E.; et al. Farmaco 2000, 55, 719–724. 27.Yang, X.; Liu, G.; Li, H.; Zhang, Y.; Song, D.; Li, C., Wang, R.; Liu, B.; Liang, W.; Jing, Y.; et al. J. Med. Chem.
  • 2010, 53, 1015–1022. 28.Luthman, K.; Borg, S.; Hacksell, U. Methods Mol. Med. 1999, 23, 1–23. 29.Flipo, M.; Desroses, M.; Lecat-Guillet, N.; Villemagne, B.; Blondiaux, N.; Leroux, F.; Piveteau, C.; Mathys, V.;
  • Flament, M-P.; Siepmann, J.; et al. J. Med. Chem. 2012, 55, 68–83. 30.Flipo, M.; Desroses, M.; Lecat-Guillet, N.; Dirie, B.; Carette, X.; Leroux, F.; Piveteau, C.; Demirkaya, F.; Lens,
  • Z.; Rucktooa, P.; et al. J. Med. Chem. 2011, 54, 2994–3010. 31.Kale, P.; Johnson, L. B. Drugs Today 2005, 41, 91–105. 32.Torres, H. A.; Hachem, R. Y.; Chemaly, R. F.; Kontoyiannis, D. P.; Raad, I, I. Lancet Infect. Dis. 2005, 5, 775–785.
  • Keating, G. M. Drugs 2005, 65, 1553–1567.
  • Cuzick, J. Drugs Today 2005, 41, 227–239.
  • Howell, A.; Buzdar, A. J. Steroid Biochem. Mol. Biol. 2005, 93, 237–247.
  • Geisler, J.; Lİnning, P. E. J. Steroid Biochem. Mol. Biol. 2005, 95, 75–81. 37.Brueggemeier, R.W.; Hackett, J.C.; Diaz-Cruz, E. S. Endocr. Rev. 2005, 26, 331–345.
  • Yin, L. M.; Wei, Y.; Wang, Y.; Xu, Y. D.; Yang Y. Q. Int. J. Med. Sci. 2013, 10, 68–72. 46.A˘gırba¸s, H.; S¨umengen, D.; D¨ur¨ust, Y.; D¨ur¨ust, N. Synth. Commun. 1992, 22, 209–217.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Graphene oxide magnetite nanocomposite as an efficient and magnetically separable adsorbent for methylene blue removal from aqueous solution

Kadem MERAL, Önder METIN

Graphene oxide--magnetite nanocomposite as an efficient and magnetically separable adsorbent for methylene blue removal from aqueous solution

Kadem MERAL, Önder METİN

QSAR study of chalcone derivatives as anti-Leishmania agents

Maryam IMAN, Asghar DAVOOD, Nasimossadat BANAROUEI

Binding of flavanone with β -CD/ctDNA: a spectroscopic investigation

Chandrasekaran SOWRIRAJAN, Sameena YOUSUF, Muthu Vijayan Enoch VIJAYARAJ ISRAEL

Synthesis, anticandidal activity, and cytotoxicity of some thiazole derivatives with dithiocarbamate side chains

Leyla YURTTAŞ, Yusuf ÖZKAY, Fatih DEMİRCİ, Gamze GÖGER, Şafak Ulusoylar YILDIRIM, Usama ABU MOHSEN, Ömer ÖZTÜRK, Zafer Asım KAPLANCIKLI

Rosmarinic acid: a potent carbonic anhydrase isoenzymes inhibitor

Meryem TOPAL, İlhami GÜLÇİN

Linear assembly and 3D networks of peptide modified gold nanoparticles

Şaban KALAY, Clement BLANCHET, Mustafa CULHA

Convenient method for synthesis of various fused heterocycles via utility of 4-acetyl-5-methyl-1-phenyl-pyrazole as precursor

Sobhi MOHAMED GOMHA, Ahmad SAMI SHAWALI, Abdou OSMAN ABDELHAMID

Ultrarapid catalytic reduction of some dyes by reusable novel erythromycin-derived silver nanoparticles

Yasmeen JUNEJO, Abdulhadi BAYKAL

Effects of functional groups of triple bonds containing molecules on nickel electroplating

Esma SEZER, Belkıs USTAMEHMETOĞLU, Ramazan KATIRCI