European Journal of Chemistry

Ultrasound assisted synthesis of pyrazolo[1,5-a]pyrimidine-antipyrine hybrids and their anti-inflammatory and anti-cancer activities

Article Sidebar

PDF CIF FILE
Published: Mar 31, 2020
DOI: https://doi.org/10.5155/eurjchem.11.1.68-79.1942
Keywords:
Aminopyrazole, 4-Aminoantipyrine, Pyrazolopyrimidines, X-ray crystallography, Ultrasound irradiation, Potassium hydrogen sulphate
Section
Research Article
Issue
Vol. 11 No. 1 (2020): March 2020
Dates
Received 2019-11-20
Accepted 2020-02-14
Published 2020-03-31
Crossmark


Main Article Content

Shunan Kaping
Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Tapesia Gardens, Sonapur 782402, Assam, India
http://orcid.org/0000-0001-7898-5039
Melboureen Sunn
Department of Biotechnology, St. Anthony’s College, Shillong 793001, Meghalaya, India
http://orcid.org/0000-0002-9377-4544
Laishram Indira Singha
Department of Biotechnology, St. Anthony’s College, Shillong 793001, Meghalaya, India
http://orcid.org/0000-0002-0360-2168
Jai Narain Vishwakarma
Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Tapesia Gardens, Sonapur 782402, Assam, India
http://orcid.org/0000-0001-9068-4554

Abstract

A series of antipyrinyl-pyrazolo[1,5-a]pyrimidines have been synthesized by reactions of aminopyrazole (4) with various formylated active proton compounds in the presence of KHSO4 (aqueous media), under ultrasound irradiation. The structures of the compounds have been established with the help of spectral and analytical data. N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-7-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide (6a) was further subjected to X-ray crystallographic studies to avoid any ambiguity of the derived structures. Crystal data for compound 6a, C51H46N12O5 (M =907.00 g/mol): triclinic, space group P-1 (no. 2), a = 9.9554(3) Å, b = 14.0875(4) Å, c = 17.4572(4) Å, α = 79.676(2)°, β = 85.283(2)°, γ = 72.647(2)°, V = 2297.97(11) Å3, Z = 2, T = 296.15 K, μ(MoKα) = 0.088 mm-1, Dcalc = 1.311 g/cm3, 29732 reflections measured (4.174° ≤ 2Θ ≤ 57.068°), 10681 unique (Rint = 0.0400, Rsigma = 0.0533) which were used in all calculations. The final R1 was 0.0566 (I > 2σ(I)) and wR2 was 0.1663 (all data). The novel compounds were also screened for their biological activities.


icon graph This Abstract was viewed 2695 times | icon graph Article PDF downloaded 872 times icon graph Article CIF FILE downloaded 0 times

How to Cite
(1)
Kaping, S.; Sunn, M.; Singha, L. I.; Vishwakarma, J. N. Ultrasound Assisted Synthesis of pyrazolo[1,5-a]pyrimidine-Antipyrine Hybrids and Their Anti-Inflammatory and Anti-Cancer Activities. Eur. J. Chem. 2020, 11, 68-79.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Elkhawaga, A. M.; El-Dean, A. M. K.; Radwan, S. M.; Ahmed, M. M. Bull. Korean Chem. Soc. 2009, 30, 561-566.

[2]. Dreassi, E.; Zizzari, A. T.; Mori, M.; Fillipi, I.; Belfiore, A.; Naldini, A.; Carraro, F.; Santucci, A.; Shenone, S.; Botta, M. Eur. J. Med. Chem. 2010, 45, 5958-5964.
https://doi.org/10.1016/j.ejmech.2010.09.062

[3]. Earl, R. A.; Pugmire, R. J.; Revanker, G. R.; Townsend, L. B. J. Org. Chem. 1975, 40, 1822-1828.
https://doi.org/10.1021/jo00900a030

[4]. Curran, K. J.; Verheijen, J. C.; Kaplan, J.; Richard, D. J.; Toral-Barza, L.; Hollander, I.; Lucas, J.; Ayral-Kaloustian, S.; Yu, K.; Zask, A. Bioorg. Med. Chem. Lett. 2010, 20, 1440-1444.
https://doi.org/10.1016/j.bmcl.2009.12.086

[5]. Hassan, A. S.; Hafez, T. S.; Osman, S. A. Sci. Pharm. 2015, 83, 27-39.
https://doi.org/10.3797/scipharm.1409-14

[6]. Ferrari, S. M.; Motta, C. L.; Sartini, S.; Baldini, E.; Materazzi, G.; Politti, U.; Ruffilli, I.; Ulisse, S.; Miccoli, P.; Antonelli, A.; Fallahi, P. Mini. Rev. Med. Chem. 2016, 16, 86-93.
https://doi.org/10.2174/1389557515666151016124208

[7]. Abdou, I. M.; Saleh, A. M.; Zohdi, H. F. Molecules 2004, 9, 109-116.
https://doi.org/10.3390/90300109

[8]. El-Feky, S. A.; Abd El-Samii, Z. K. Pharmazie 1996, 51, 540-543.

[9]. Davies, L. P.; Brown, D. J.; Chow, S. C.; Johnston, G. A. Neurosci. Lett. 1983, 41, 189-193.
https://doi.org/10.1016/0304-3940(83)90245-8

[10]. Ghorab, M. M.; Ismail, Z. H.; Abdel-Gawad, S. M.; Aziem, A. A. Heteroatom. Chem. 2004, 15, 57-62.
https://doi.org/10.1002/hc.10212

[11]. Mohamed, H. A.; Abdel-Wahab, B. F.; Abdel-Latif, E. J. Chem. Pharm. Res. 2015, 7, 1218-1222.

[12]. Stefano, A.; Anna, A.; Maurizio, B.; Alessandra, T.; Francisco, O.; Francesco, O.; Silvia, S.; Chiara, B.; Matilde, Y. Chem. Med. Chem. 2010, 5, 1242-1251.

[13]. Fraley, M. E.; Hambaugh, S. R.; Rubino, R. S.; Hungate, R. W. US Patent 2007, 7, 262, 199.

[14]. Senga, K.; Novinson, T.; Wilson, H. R. J. Med. Chem. 1981, 24, 610-613.
https://doi.org/10.1021/jm00137a023

[15]. Schenone, S.; Brullo, C.; Bruno, O.; Bondavalli, F.; Mosti, L.; Maga, G.; Crespan, E.; Carraro, F.; Manetti, F.; Tintori, C.; Botta, M, Eur. J. Med. Chem. 2008, 43, 2665-2676.
https://doi.org/10.1016/j.ejmech.2008.01.034

[16]. George, C. F. P. Lancet 2001, 358, 1623-1626.
https://doi.org/10.1016/S0140-6736(01)06656-9

[17]. Lutsevich, A. N.; Bender, K. I.; Reshetko, O. V. Eksp. Klin. Farmakol. 1995, 58, 51-55.

[18]. Turan-Zitouni, G.; Sivaci, M.; Kiliç, F. S.; Erol, K. Eur. J. Med. Chem. 2001, 36, 685-689.
https://doi.org/10.1016/S0223-5234(01)01252-1

[19]. Acheson, R. M. Introduction to Chemistry of Heterocyclic Compounds, 4th edition, John Wiley & Sons, 2009, p. 354.

[20]. Bondock, S.; Rabie, R.; Etman, H. A.; Fadda, A. A. Eur. J. Med. Chem. 2008, 43, 2122-2129.
https://doi.org/10.1016/j.ejmech.2007.12.009

[21]. Metwally, M. A.; Gouda, M. A.; Harmal, A. N.; Khalil, A. M. J. Med. Chem. 2012, 56, 254-262.
https://doi.org/10.1016/j.ejmech.2012.08.034

[22]. Yoo, J.; Thai, K.; Kim, D.; Lee, J. Y.; Park, H. Bioorg. Med. Chem. Lett. 2007, 17, 4271-4274.
https://doi.org/10.1016/j.bmcl.2007.05.064

[23]. Devi, A. S.; Kaping, S.; Vishwakarma, J. N. Mol. Divers. 2015, 19, 759-771.

[24]. Kaping, S.; Kalita, U.; Sunn, M.; Singha, L. I.; Vishwakarma, J. N. Monatsh. Chem. 2016, 147, 1257-1276.
https://doi.org/10.1007/s00706-015-1638-x

[25]. Kaping, S.; Boiss, I.; Singha, L. I.; Helissey, P.; Vishwakarma, J. N. Mol. Divers. 2016, 20, 379-390.
https://doi.org/10.1007/s11030-015-9639-6

[26]. Buriol, L.; Munchen, T. S.; Frizzo, C. P.; Marzari M. R. B.; Zanatta N.; Bonacorso, H. G.; Martins, M. A. P. Ultrason. Sonochem. 2013, 20, 1139-1143.
https://doi.org/10.1016/j.ultsonch.2013.02.006

[27]. Bharath, Y.; Rao, M. V. B.; Pal, M. Lett. Drug Design Discover. 2017, 14, 1206-1214.
https://doi.org/10.2174/1570180814666170125125654

[28]. Dandia, A.; Gupta, S. L.; Parewa, V. RSC Adv. 2014, 4, 6908-6915.
https://doi.org/10.1039/c3ra47231k

[29]. Farrugia, L. J.; J. Appl. Cryst. 2012, 45, 849-854.
https://doi.org/10.1107/S0021889812029111

[30]. Chanda, K.; Dutta, M. C.; Karim, E.; Vishwakarma, J. N. J. Indian Chem. Soc. 2004, 81, 791-793.

[31]. Dutta, M. C.; Chanda, K.; Karim, E.; Vishwakarma, J. N. Ind. J. Chem. 2004, 36, 2471-2474.

[32]. Fadda, A. A.; Bondock, S.; Rabie. R.; Etman, H. A. Turk. J. Chem. 2008, 32, 259-286.

[33]. Gopalsamy, A.; Ciszewski, G.; Shi, M.; Berger, D.; Hu, Y.; Lee, F.; Feldberg, L.; Frommer, E.; Kim, S.; Collins, K.; Wojciechowicz, D.; Mallon, R. Biorg. Med. Chem. Lett. 2009, 19, 6890-6892.
https://doi.org/10.1016/j.bmcl.2009.10.074

[34]. Lai, S. C.; Peng, W. H.; Huang, S. C. Ho, Y. L.; Huang, J. H.; Lai, Z.; Chang, Y. Am. J. Chin. Med. 2009, 37, 573-588.
https://doi.org/10.1142/S0192415X09007065

[35]. Houwen, B. Lab. Hematol. 2000, 6, 1-7.

[36]. Freshney, R. I.; Culture of animal cells: A Manual of Basic Technique and Specialized Application, 6th edition; John Wiley and Sons: New Jersey, 2010, p. 373-375.
https://doi.org/10.1002/9780470649367

[37]. Sheldrick, G. M. SHELXL97. Program for the Refinement of Crystal Structures, University of Gottingen, Germany, 1997.

[38]. Portilla, J.; Quiroga, J.; Cobo, J.; Low, J. N.; Glidewell, C. Acta. Cryst. C 2006, 62, 186-189.
https://doi.org/10.1107/S0108270106005373

[39]. Ahmad, F.; Khan, R.; Rasheed, S. J. Islamic Acad. Sci. 1992, 5, 111-114.

[40]. Kang, O. H.; Chae, H. S.; Oh, Y. C.; Choi, J. G.; Lee, Y. S.; Jang, H. J.; Kim, J. H.; Kim, Y. C.; Sohn, D. H.; Park, H.; Kwon, D. Y. Am. J. Chin. Med. 2008, 36, 913-928.
https://doi.org/10.1142/S0192415X0800634X

[41]. Khan, F. H. The Elements of Immunology, 1st edition, Pearson Education India, 2009.

[42]. Alam, A.; Imliwati, L.; Rapthap, C.; Singh, V. Ind. J. Exp. Biol. 2001, 39, 201-208.

Supporting Agencies

Department of Biotechnology, Ministry of Science and Technology, Government of India, New Delhi-110 003, India.
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).