Synthesis and in Vitro Antitumor Activity of a Novel Series of 2-Pyrazoline Derivatives Bearing the 4-Aryloxy-7-chloroquinoline Fragment

Molecules

Alba Montoya¹  Jairo Quiroga¹  Rodrigo Abonia¹  Manuel Nogueras²  Justo Cobo²  Braulio Insuasty¹ 

[1] Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Apartado Aéreo 25360, Colombia; E-Mails:;Department of Inorganic and Organic Chemistry, Universidad de Jaén, Jaén 23071, Spain; E-Mails:

关键词: microwave irradiation;    Claisen-Schmidt condensation;    chalcones;    cyclocondensation reaction;    2-pyrazolines;    antitumor activity;   

DOI  :  10.3390/molecules191118656

来源: mdpi

【 摘 要 】

A new series of NH-pyrazoline derivatives 6 was synthesized by cyclocondensation reaction of novel [(7-chloroquinolin-4-yl)oxy]chalcones 5 with hydrazine hydrate. The treatment of pyrazolines 6 with acetic anhydride or formic acid yielded the N-acetyl- or N-formylpyrazoline derivatives 7–8, respectively. These novel 2-pyrazoline derivatives 6–8 were evaluated by the U.S. National Cancer Institute (NCI). Compounds 7b,d,f and 8c,f showed remarkable antitumor activity against 58 cancer cell lines, with the most important GI₅₀ values from in vitro assays ranging from 0.48 to 1.66 μM. The 2-pyrazoline derivatives bearing the 4-aryloxy-7-chloroquinoline fragment are thus considered to be useful leads for the rational design of new antitumor agents.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.