Copyright (c) 2023 Kotaiah Kandula, Nagaraju Myakala, Nagamani Rayala, Satheesh Kuna, Sumathi Vodnala, Vishnu Thumma, A.K.D. Bhavani
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Novel Series of 1,2,3-Triazoles Tethered to Pyrazolo[3,4-d]pyrimidine Scaffold with Methoxyphenoxy Linker
Corresponding Author(s) : A.K.D. Bhavani
Asian Journal of Chemistry,
Vol. 35 No. 12 (2023): Vol 35 Issue 12, 2023
Abstract
A novel series of hybrid heterocycles having pyrazolopyrimidine based 1,2,3-triazole scaffold with two ether linkages were synthesized by 1,3-dipolar cycloaddition reaction of pyrazolopyrimidines tethered to phenoxy alkynes and differently substituted aromatic azides using CuSO4·5H2O and sodium ascorbate mixture as catalyst in DMSO-H2O solvent mixture. The synthesized triazole hybrids were characterized by using various spectroscopic techniques.
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References
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M. Chauhan and R. Kumar, Bioorg. Med. Chem., 21, 5657 (2013); https://doi.org/10.1016/j.bmc.2013.07.027
M.C. Bagley, M. Baashen, V.L. Paddock, D. Kipling and T. Davis, Tetrahedron, 69, 8429 (2013); https://doi.org/10.1016/j.tet.2013.07.055
V. Masevicius, R. Juskenas and S. Tumkevicius, J. Heterocycl. Chem., 49, 315 (2012); https://doi.org/10.1002/jhet.724
M.H. Elnagdi, M.R.H. Elmoghayar and G.E.H. Elgemeie, Adv. Heterocycl. Chem., 41, 319 (1987); https://doi.org/10.1016/S0065-2725(08)60164-6
M.R. Shaaban, T.S. Saleh, A.S. Mayhoub, A. Mansour and A.M.S. Farag, Bioorg. Med. Chem., 16, 6344 (2008); https://doi.org/10.1016/j.bmc.2008.05.011
T. Shiota, T. Yamamori, K. Sakai, M. Kiyokawa, T. Honma, M. Ogawa, K. Hayashi, N. Ishizuka, K. Matsumura, M. Hara, M. Fujimoto, T. Kawabata and S. Nakajima, Chem. Pharm. Bull., 47, 928 (1999); https://doi.org/10.1248/cpb.47.928
P. Modi, S. Patel and M. Chhabria, Bioorg. Chem., 87, 240 (2019); https://doi.org/10.1016/j.bioorg.2019.02.044
C.S. de Melo, T.-S. Feng, R. van der Westhuyzen, R.K. Gessner, L.J. Street, G.L. Morgans, D.F. Warner, A. Moosa, K. Naran, N. Lawrence, H.I.M. Boshoff, C.E. Barry III, C.J. Harris, R. Gordon and K. Chibale, Bioorg. Med. Chem., 23, 7240 (2015); https://doi.org/10.1016/j.bmc.2015.10.021
N. Petek, B. Štefane, M. Novinec and J. Svete, Bioorg. Chem., 84, 226 (2019); https://doi.org/10.1016/j.bioorg.2018.11.029
D.A. Griffith, D.M. Hargrove, T.S. Maurer, C.A. Blum, S. De Lombaert, J.K. Inthavongsay, L.E. Klade, C.M. Mack, C.R. Rose, M.J. Sanders and P.A. Carpino, Bioorg. Med. Chem. Lett., 21, 2641 (2011); https://doi.org/10.1016/j.bmcl.2010.12.116
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I.K. Boddy, G.G. Briggs, R.P. Harrison, T.H. Jones, M.J. O’Mahony, I.D. Marlow, B.G. Roberts, R.J. Willis, R. Bardsley and J. Reid, Pestic. Sci., 48, 189 (1996); https://doi.org/10.1002/(SICI)1096-9063(199610)48:2<189::AID-PS461>3.0.CO;2-#
M. de Lourdes G. Ferreira, L.C.S. Pinheiro, O.A. Santos-Filho, M.D.S. Peçanha, C.Q. Sacramento, V. Machado, V.F. Ferreira, T.M.L. Souza and N. Boechat, Med. Chem. Res., 23, 1501 (2014); https://doi.org/10.1007/s00044-013-0762-6
L.-S. Feng, M.-J. Zheng, F. Zhao and D. Liu, Arch. Pharm. (Weinheim), 354, 2000163 (2021); https://doi.org/10.1002/ardp.202000163
H.B. Lazrek, M. Taourirte, T. Oulih, J. Barascut, J. Imbach, C. Pannecouque, M. Witrouw and E. De Clercq, Nucleosides Nucleotides Nucleic Acids, 20, 1949 (2001); https://doi.org/10.1081/NCN-100108325
S.G. Agalave, S.R. Maujan and V.S. Pore, Chem. Asian J., 6, 2696 (2011); https://doi.org/10.1002/asia.201100432
A. Kamal, N. Shankaraiah, V. Devaiah, K.L. Reddy, A. Juvekar, S. Sen, N. Kurian and S. Zingde, Bioorg. Med. Chem. Lett., 18, 1468 (2008); https://doi.org/10.1016/j.bmcl.2007.12.063
Y. Laamari, A. Oubella, A. Bimoussa, A.-E. El Mansouri, E.M. Ketatni, O. Mentre, M.Y. Ait Itto, H. Morjani, M. Khouili and A. Auhmani, Bioorg. Chem., 115, 105165 (2021); https://doi.org/10.1016/j.bioorg.2021.105165
A.K. Jordão, P.C. Sathler, V.F. Ferreira, V.R. Campos, M.C.B.V. de Souza, H.C. Castro, A. Lannes, A. Lourenco, C.R. Rodrigues, M.L. Bello, M.C.S. Lourenço, G.S.L. Carvalho, M.C.B. Almeida, A.C. Cunha and V.F. Ferreira, Bioorg. Med. Chem., 19, 5605 (2011); https://doi.org/10.1016/j.bmc.2011.07.035
M.L. Ferreira, M.V.N. Souza, S.M.S.V. Wardell, J.L. Wardell, T.R.A. Vasconcelos, V.F. Ferreira and M.C.S. Lourenço, J. Carbohydr. Chem., 29, 265 (2010); https://doi.org/10.1080/07328303.2010.511749
X.-L. Wang, K. Wan and C.-H. Zhou, Eur. J. Med. Chem., 45, 4631 (2010); https://doi.org/10.1016/j.ejmech.2010.07.031
L.V.R. Reddy, P. Venkat Reddy, N.N. Mishra, P.K. Shukla, G. Yadav, R. Srivastava and A.K. Shaw, Carbohydr. Res., 345, 1515 (2010); https://doi.org/10.1016/j.carres.2010.03.031
S. Palhagen, R. Canger, O. Henriksen, J.A. van Parys, M.E. Riviere and M.A. Karolchyk, Epilepsy Res., 43, 115 (2001); https://doi.org/10.1016/S0920-1211(00)00185-6
A.K. Jordão, V.F. Ferreira, T.M.L. Souza, G.G. de Souza Faria, V. Machado, J.L. Abrantes, M.C.B.V. de Souza and A.C. Cunha, Bioorg. Med. Chem., 19, 1860 (2011); https://doi.org/10.1016/j.bmc.2011.02.007
M. Allam, A.K.D. Bhavani, A. Mudiraj, N. Ranjan, M. Thippana and P.P. Babu, Eur. J. Med. Chem., 156, 43 (2018); https://doi.org/10.1016/j.ejmech.2018.06.055
V.H. Kapupara, D.G. Gojiya, T.D. Bhatt, S.D. Hadiyal, D.H.S. Joshi, Russ. J. Bioorgan. Chem., 46, 803 (2020); https://doi.org/10.1134/S1068162020050106
K. Somakala, S. Tariq and M. Amir, Bioorg. Chem., 87, 550 (2019); https://doi.org/10.1016/j.bioorg.2019.03.037