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. 2011 Nov;20(8):1402-1410.
doi: 10.1007/s00044-010-9495-y. Epub 2010 Nov 17.

Synthesis and in vitro antiproliferative activity of novel (4-chloro- and 4-acyloxy-2-butynyl)thioquinolines

Stanisław Boryczka, Wojciech Mól, Magdalena Milczarek, Joanna Wietrzyk, Ewa Bębenek

Synthesis and in vitro antiproliferative activity of novel (4-chloro- and 4-acyloxy-2-butynyl)thioquinolines

Stanisław Boryczka et al. Med Chem Res. 2011 Nov.

Abstract

The series of new acetylenic thioquinolines containing propargyl, 4-chloro-2-butynyl, and 4-acyloxy-2-butynyl groups have been prepared and tested for antiproliferative activity in vitro against human [SW707 (colorectal adenocarcinoma), CCRF/CEM (leukemia), T47D (breast cancer)] and murine [P388 (leukemia), B16 (melanoma)] cancer lines. Most of the obtained compounds exhibited antiproliferative activity, especially compounds 8, 12, and 21 showed the ID(50) values ranging from 0.4 to 3.8 μg/ml comparable to that of cisplatin used as reference compounds.

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Figures

Scheme 1
Scheme 1
Synthesis of 4-chloro-3-(4-chloro-2-butynylthio)quinoline 6. Reagents and conditions: a MeONa, DMSO, 25°C, 30 min; b 1-bromo-4-chloro-2-butyne, NaOHaq, 25°C, 30 min
Scheme 2
Scheme 2
Synthesis of acetylenic thioquinolines 7–12. Reagents and conditions: a CS(NH2)2 or CSe(NH2)2, EtOH, 25°C, 1 h; b NaOHaq, c 1-bromo-4-chloro-2-butyne, NaOHaq, 25°C, 30 min
Scheme 3
Scheme 3
Synthesis of acetylenic thioquinolines 16–25. Reagents and conditions: a o-phthalic anhydride or cinnamoyl chloride, pyridine, benzene, 70°C, 1 h; b o-phthalic anhydride or cinnamoyl chloride or benzoyl chloride or ethyl chloroformate, pyridine, benzene, 70°C, 1 h
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