Synthesis and Anti‐tumor Activities of Novel Pyrazolo[1,5‐a]pyrimidines

Abstract

A series of novel pyrazolo[1,5-a]pyrimidines were designed and synthesized in order to find novel potent anti-tumor compounds. The structures of all the compounds were confirmed by IR, (1)H-NMR, elemental analysis, and MS. Their anti-tumor activities against cancer cell lines were tested by the MTT method in vitro. Compound 19 displayed potent anti-tumor activity.

Synthesis and Biological Evaluation of 7-(2-Chlorophenylamino)-5-((2- [18F]fluoro-ethyoxy)methyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile as PET Tumor Imaging Agent

“…The synthesis route to 1 followed a procedure described previously [9]. Substitution of 7-Cl in 1 with 2-chloroaniline produced 2.…”

“…7-Chloro-5-(chloromethyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (1), shown in Scheme 1, was synthesized as described previously [9]. A solution of 1 (7.9 g, 35 mmol) in 2-propanol (5 mL) was mixed with 2-chloroaniline (4.7 mL, 45 mmol) and stirred at 60 • C for 3 h. After being cooled to room temperature, the precipitate was filtered, washed thoroughly with isopropanol, and then crystallized from methanol to produce product 2 (9.…”

“…Furthermore, the pyrazolo[1,5-a]pyrimidine core structure has several positions for introducing a substituent, the C-5 and the C-7 position have commonly been used for introducing substituents in anti-tumor drug design [8 -13]. Recently, a series of novel 3-cyano-5,7-disubstituted pyrazolo [1,5-a]pyrimidine derivatives with various C-7 aniline substituents and C-5 amino alkoxy moieties have been synthesized and showed that pyrazolo [1,5-a]pyrimidine analogs of purine have strong anti-cancer activity [9].…”

Heterocyclic Synthesis Via Enaminonitriles: One-Pot Synthesis of Some New Pyrazole, Pyrimidine, Pyrazolo[1,5-A]Pyrimidine and Pyrido[2,3-D]Pyrimidine Derivatives

“…Pyrazo lo [1,5-a]pyrimidine are of considerable chemical and pharmacological impo rtance as purine analogs and many derivatives of pyrazolo [1,5-a]pyrimidines have been reported to exhibit cyotoxic activity [1][2][3][4][5][6][7][8][9]. Several 7-substituted pyrazolo [1,5-a]pyrimid ine derivatives were reported to have antiproliferative act ivity against HCT116 and other cell lines (e.g.…”

Synthesis of some new indole derivatives containing pyrazoles with potential antitumor activity

“…13 On the other hand, over the past two decades, pyrazole-containing compounds have received considerable attention owing to their diverse chemotherapeutic potentials including versatile antineoplastic activities. Literature survey revealed that some pyrazoles have been implemented as antileukemic, [14][15][16] antitumor [17][18][19][20] and anti-proliferative 21,22 agents, beside their capability to exert remarkable anticancer effects through inhibiting different types of enzymes that play important roles in cell division. [23][24][25] We have recently reported synthesis and antitumor activity of some indole derivatives containing 1,3,4-oxadiazole and 1,2,4-triazole A, and discovered that some of the analogs are potent and selective against various cancer cell lines.…”