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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 (=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)°, = 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.


Keywords


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

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DOI: 10.5155/eurjchem.11.1.68-79.1942

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Funding information


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

Citations

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[1]. 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
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[2]. 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
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[3]. 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
/


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Supporting information


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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. 28 Nov. 2021
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)

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