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TRUCTURE OF ORGANIC COMPOUNDS

Synthesis, Crystal Structure and Biological Activity of 7-(4-Methylpiperazin-1-yl)-5-[4(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-Carbonitrile Yi-Lin Gonga, Peng Daib, Ye Chena, Shi Dinga, and Ju Liua,* a

Key Laboratory of New Drug Research and Development of Liaoning Province, College of Pharmacy, Liaoning University, Shenyang, 110036 China b

Physical and Chemical Laboratory, Shenyang Center for Disease Control and Prevention, Shenyang, 110031 China *e-mail: [email protected] Received May 16, 2019; revised December 17, 2019; accepted December 19, 2019

Abstract—The title compound C19H17F3N6 was synthesized and structurally characterized by infrared and mass spectroscopy, 1H NMR, elemental analyses and single crystal X-ray diffraction. The compound crystallizes in monoclinic system, space group P21/c with a = 17.097(4) Å, b = 7.1668(16) Å, c = 18.389(3) Å, β = 118.251(15)°, V = 1984.8(8) Å3, Z = 4, Dc = 1.293 g cm–3, F(000) = 800, μ(MoKα) = 0.10 mm–1, R1 = 0.0667, and wR2 = 0.2084 for reflections with I > 2σ(I). Pyrazolo[1,5-a]pyrimidine and phenyl ring are almost coplanar, and the piperazine ring is in a chair conformation. The crystal structure is stabilized by C–H⋅⋅⋅N hydrogen interactions and a number of weak π⋅⋅⋅π interactions. In addition, the results of the determination of biological activity showed that the compound exhibited significant inhibitory activity against K562 and MKN45 cancer cell lines.

DOI: 10.1134/S1063774520070068

INTRODUCTION

against two human cancer cell lines (K562 and MKN45) using MTT assay.

In the past few decades, there is an urgent need to pay much attention to the design, synthesis and production of more potent and effective therapeutic agents to treat human cancer diseases, which is for the cause of major deaths worldwide [1, 2]. Various derivatives of pyrazolopyrimidines attract the attention of medicinal chemists because of their biological and chemotherapeutic importance [3]. Among them, analogues of pyrazolo[1,5-a]pyrimidine were found to have a number of biological activities, such as antitumor [4, 5], antifungal [6], antibacterial [7], analgesics [8], anti-inflammatory [9]. Based on the previous findings of biological effectiveness of pyrazolo[1,5a]pyrimidine derivatives and the continuation of our research program for the synthesis of new compounds exhibiting biological activity [10–12], we synthesized a new pyrazolo[1,5-a]pyrimidine derivative, 7-(4methylpiperazin-1-yl)-5-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile by three-step synthesis and evaluated its anticancer properties

EXPERIMENTAL Materials and Methods Unless otherwise specified, all starting materials and reagents were obtained from commercial supplies without further purification. All melting points were obtained with a Beijing Taike X-4 microscopy melting point apparatus and were uncorrected. 1H NMR spectra were recorded on a Bruker Biospin 600 MHz or Bruker Biospin 300 MHz instrument using TMS as the internal standard. All chemical shifts were