Design, Synthesis, and Evaluation of a New Series of 2-Pyrazolines as Potential Antileukemic Agents

Abstract

In an attempt to identify small molecules for the treatment of leukemia, 12 new pyrazolines (2a−l) were synthesized efficiently. WST-1 assay was performed to examine their cytotoxic features on HL-60 human acute promyelocytic leukemia (APL), K562 human chronic myeloid leukemia (CML), and THP-1 human acute monocytic leukemia cells. Four compounds (2e, 2f, 2g, and 2h) were determined as promising antileukemic agents on HL-60 and K562 cells. IC 50 values of compounds 2f, 2h, 2e, 2g, and bortezomib for the HL-60 cell line were found as 33.

Design, Synthesis, and Evaluation of New Pyrazolines As Small Molecule Inhibitors of Acetylcholinesterase

“…The absence of this band in the IR spectra of compounds 2a – l revealed that the cyclization reaction occurred efficiently for the formation of the pyrazoline ring. The 1 H NMR spectra of compounds 2a – l confirmed the presence of the ABX pattern (Figure ), which is a characteristic feature of the 1 H NMR spectra for the 2-pyrazoline core . In their 1 H NMR spectra, the H A , H B, and H X protons of the pyrazoline ring gave rise to the doublet of doublets at 3.00–3.14, 3.78–3.90 and 5.21–5.51 ppm, respectively, with J AB = 16.15–17.65 Hz, J BA = 17.25–17.65 Hz, J AX = 4.70–7.20 Hz, and J BX = 11.80–12.05 Hz.…”

“…The 1 H NMR spectra of compounds 2a – l confirmed the presence of the ABX pattern ( Figure 3 ), which is a characteristic feature of the 1 H NMR spectra for the 2-pyrazoline core. 34 In their 1 H NMR spectra, the H A , H B, and H X protons of the pyrazoline ring gave rise to the doublet of doublets at 3.00–3.14, 3.78–3.90 and 5.21–5.51 ppm, respectively, with J AB = 16.15–17.65 Hz, J BA = 17.25–17.65 Hz, J AX = 4.70–7.20 Hz, and J BX = 11.80–12.05 Hz. In the 13 C NMR spectra of compounds 2a – l , the signals were observed in the region 150.66–150.91, 44.28–44.65, and 61.89–64.00 ppm corresponding to the C3, C4, and C5 carbons of the pyrazoline skeleton, respectively.…”

“…The precipitated solid was filtered, washed with water, and dried. The product was crystallized from ethanol. , …”