Ultrasound Assisted Synthesis of 2-alkynyl Pyrazolo[1,5-a]pyrimidines as Potential Anti-cancer Agents

Bharath, Yarlagadda; Rao, Mandava V. Basaveswara; Pal, Manojit

doi:10.2174/1570180814666170125125654

Cited by 5 publications

(1 citation statement)

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“…In view of these information and in continuation with our research work [23][24][25] on synthesis of pharmacologically important pyrazolo [1,5-a]pyrimidines, it was found worthy to synthesize novel pyrazolo[1,5-a]pyrimidines incorporating the antipyrine moiety to study their biological properties. Ultrasound (US) irradiation has helped researchers tremendously in accomplishing the green goals of chemistry by shortening the reaction time with easy work-up, resulting in high yields of the products and use of readily available solvents and catalysts [26][27][28]. Ultrasound tool has been advantageously employed to achieve the desired synthesis.…”

Section: Introductionmentioning

confidence: 99%

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

Kaping

Sunn²,

Singha³

et al. 2020

Eur J Chem

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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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