European Journal of Chemistry

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

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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
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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.


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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.

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Supporting Agencies

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