European Journal of Chemistry 2020, 11(1), 68-79 | doi: https://doi.org/10.5155/eurjchem.11.1.68-79.1942 | Get rights and content

Issue cover




Crossmark

  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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


Shunan Kaping (1) orcid , Melboureen Sunn (2) orcid , Laishram Indira Singha (3) orcid , Jai Narain Vishwakarma (4,*) orcid

(1) Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Tapesia Gardens, Sonapur 782402, Assam, India
(2) Department of Biotechnology, St. Anthony’s College, Shillong 793001, Meghalaya, India
(3) Department of Biotechnology, St. Anthony’s College, Shillong 793001, Meghalaya, India
(4) Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Tapesia Gardens, Sonapur 782402, Assam, India
(*) Corresponding Author

Received: 20 Nov 2019 | Revised: 11 Feb 2020 | Accepted: 14 Feb 2020 | Published: 31 Mar 2020 | Issue Date: March 2020

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.


Announcements


One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and May 31, 2023 (Voucher code: SPONSOR2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


Aminopyrazole; 4-Aminoantipyrine; Pyrazolopyrimidines; X-ray crystallography; Ultrasound irradiation; Potassium hydrogen sulphate

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.11.1.68-79.1942

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 2064 times | icon graph PDF Article downloaded 456 times

Funding information


Department of Biotechnology, Ministry of Science and Technology, Government of India, New Delhi-110 003, India.

Citations

/


[1]. Mohamed M. Hammouda, Hatem E. Gaffer, Khaled M. Elattar
Insights into the medicinal chemistry of heterocycles integrated with a pyrazolo[1,5-a]pyrimidine scaffold
RSC Medicinal Chemistry  13(10), 1150, 2022
DOI: 10.1039/D2MD00192F
/

[2]. SUSMA DAS, SHIVANGI BORKOTOKY, MAXMILLANDO RYMBAI, VEDANT V BORAH, JAYANTI D ROY, SHUNAN KAPING, PHILIPPE HELISSEY, JAI N VISHWAKARMA
Novel ferrocene-pyrazolo[1,5-a]pyrimidine hybrids: A facile environment-friendly regioselective synthesis, structure elucidation, and their antioxidant, antibacterial, and anti-biofilm activities
Journal of Chemical Sciences  134(3), , 2022
DOI: 10.1007/s12039-022-02064-y
/

[3]. Susma Das, Shilpika Khanikar, Shunan Kaping, Jayanti Datta Roy, Arnab Sen, Philippe Helissey, Jai Narain Vishwakarma
Efficient synthesis of diversely substituted pyrazolo[1,5-a]pyrimidine derivatives promoted by ultrasound irradiation in water and their antibacterial activities
European Journal of Chemistry  11(4), 304, 2020
DOI: 10.5155/eurjchem.11.4.304-313.2033
/

[4]. V. L. Gein, T. M. Zamaraeva, M. V. Dmitriev
Synthesis and Structure of 9-Aryl-8-aryl(fur-2-yl)-4,9-dihydrotetrazolo[1′,5′:1,2]pyrimido[4,5-d]pyridazin-5(6H)-ones
Russian Journal of General Chemistry  91(8), 1444, 2021
DOI: 10.1134/S107036322108003X
/

[5]. Sherif M.H. Sanad, Mohamed S. Mohamed Ahmed, Ahmed E.M. Mekky, Zeinab A. Abdallah
Regioselective synthesis and theoretical calculations of Bis(pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidines) linked to benzofuran units via piperazine spacer: A DFT, MM2, and MMFF94 study
Journal of Molecular Structure  1243, 130802, 2021
DOI: 10.1016/j.molstruc.2021.130802
/

[6]. Nehal A. Hamdy, Mardia T. El Sayed, Hoda A. R. Hussein, Marwa M. Mounier, Manal M. Anwar
Synthesis of novel heterocyclic compounds bearing tetralin moiety of potential anticancer activity targeting the intrinsic apoptotic pathway
Synthetic Communications  53(4), 298, 2023
DOI: 10.1080/00397911.2023.2172348
/

[7]. Mehdi Messaad, Slim Elleuch, Mohamed Kossentini
LE and ICT properties of pyrazolo[1,5-a]pyrimidines based dyes: Experiments and DFT/TDDFT calculations
Journal of Luminescence  257, 119772, 2023
DOI: 10.1016/j.jlumin.2023.119772
/

[8]. Moustafa Sherif Moustafa, Ahmed Moukhtar Nour-Eldeen, Saleh Mohamed Al-Mousawi, Afaf Abd El-Hameed, Michael Magdy, Kamal Usef Sadek
Regioselectivity in the reaction of 5-amino-3-anilino-1H-pyrazole-4-carbonitrile with cinnamonitriles and enaminones: Synthesis of functionally substituted pyrazolo[1,5-a]pyrimidine derivatives
Green Processing and Synthesis  11(1), 116, 2022
DOI: 10.1515/gps-2022-0009
/

[9]. Susma Das, Labet Bankynmaw Marpna, Jai Narain Vishwakarma
Efficient, environment friendly and regioselective synthetic strategy for 2/3-substituted-8,8-dimethyl-8,9-dihydropyrazolo[1,5-a]quinazolin-6(7H)-ones and their structure elucidation
European Journal of Chemistry  13(1), 41, 2022
DOI: 10.5155/eurjchem.13.1.41-48.2168
/

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 information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Kaping, S.; Sunn, M.; Singha, L.; Vishwakarma, J. Eur. J. Chem. 2020, 11(1), 68-79. doi:10.5155/eurjchem.11.1.68-79.1942
Kaping, S.; Sunn, M.; Singha, L.; Vishwakarma, J. Ultrasound assisted synthesis of pyrazolo[1,5-a]pyrimidine-antipyrine hybrids and their anti-inflammatory and anti-cancer activities. Eur. J. Chem. 2020, 11(1), 68-79. doi:10.5155/eurjchem.11.1.68-79.1942
Kaping, S., Sunn, M., Singha, L., & Vishwakarma, J. (2020). Ultrasound assisted synthesis of pyrazolo[1,5-a]pyrimidine-antipyrine hybrids and their anti-inflammatory and anti-cancer activities. European Journal of Chemistry, 11(1), 68-79. doi:10.5155/eurjchem.11.1.68-79.1942
Kaping, Shunan, Melboureen Sunn, Laishram Indira Singha, & Jai Narain Vishwakarma. "Ultrasound assisted synthesis of pyrazolo[1,5-a]pyrimidine-antipyrine hybrids and their anti-inflammatory and anti-cancer activities." European Journal of Chemistry [Online], 11.1 (2020): 68-79. Web. 29 May. 2023
Kaping, Shunan, Sunn, Melboureen, Singha, Laishram, AND Vishwakarma, Jai. "Ultrasound assisted synthesis of pyrazolo[1,5-a]pyrimidine-antipyrine hybrids and their anti-inflammatory and anti-cancer activities" European Journal of Chemistry [Online], Volume 11 Number 1 (31 March 2020)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.11.1.68-79.1942


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2020, 11(1), 68-79 | doi: https://doi.org/10.5155/eurjchem.11.1.68-79.1942 | Get rights and content

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c) 2020 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/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 (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).


© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.