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Synthesis and antitumor activity of novel 2 alkylthio-N-(4-R-quinazolin-2-yl)benzenesulfonamides

Jarosław J. Sławiński ,  Aneta Pogorzelska ,  Beata Żołnowska ,  Kamila Hablutzel 

Medical University of Gdańsk, Department of Organic Chemistry, Gen. J. Hallera Street 107, Gdańsk 80-416, Poland

Abstract
Our recent studies on 2-benzylthiobenzenesulfonamides revealed that a number of their N-substituted derivatives possess substantial in vitro antitumor activity [1-5]. This prompted us to develop a facile method for the synthesis a new series of sulfonamides bearing heterocyclic rings attached to the sulfonamide nitrogen atom. The synthesis of the target 2-alkylthio-4-chloro-N-(4-R3-quinazolin-2-yl)benzenesulfonamides were achieved by reacting of the corresponding N-(2-alkylthiobenzenesulfonyl)cyanamide potassium salts with suitable ortho-substituted anilines, such as o-aminoacetophenone or o-aminobenzophenone derivatives in glacial acetic acid.

Fourteen of compounds obtained were screened at the NCI (Bethesda MD, USA) for their in vitro activities against NCI-60 panel of human cancer cell lines. Many of these compounds exhibited a pronounced activity against numerous cancer cell lines. They noticed that, the susceptibility of individual subpanels to the tested compounds was being arranged in the following order: leukemia, non-small cell lung cancer, melanoma, colon, prostate and renal cancer, while the number of leukemia and lung cancer cell lines was largest.

References:

[1]. Sławiński J., Eur. J. Med. Chem. 39, 179 (2004)

[2]. Sławiński J., Gdaniec M.  Eur. J. Med. Chem. 40, 377 (2005).

[3]. Sławiński J., Brzozowski Z., Eur. J. Med. Chem. 41, 1180 (2006).

[4]. Sławiński J., Brożewicz K., Fruziński A., Główka M.L. Heterocycles, 83, 1093 (2011).

[5]. Brożewicz K., Sławiński J., Monatsh. Chem. doi:10.1007/s00706-012-0732-6 (2012).

 

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Presentation: Poster at VIII Multidyscyplinarna Konferencja Nauki o Leku, by Jarosław J. Sławiński
See On-line Journal of VIII Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2012-03-07 08:29
Revised:   2012-03-07 10:21