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Sci. Pharm. 2013, 81(2), 423-436; doi:10.3797/scipharm.1301-13

Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety

1
Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine
2
Present address: Mutabilis, 102 Avenue Gaston Roussel, 93230 Romainville, France
*
Author to whom correspondence should be addressed.
Received: 14 January 2013 / Accepted: 4 February 2013 / Published: 4 February 2013
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Abstract

Novel 11-substituted 3,11-dihydro-2H-benzo[6,7]thiochromeno[2,3-d][1,3]-thiazole-2,5,10-triones 4a–i were synthesized in 75–90% yields via the hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with 1,4-naphtho-quinone. The synthesized compounds were evaluated for their antineoplastic and antimycobacterial activities. A moderate selectivity against melanoma cancer cells (GI50 (UACC-257-melanoma) = 0.22 μM) was demonstrated for 4i, whereas derivatives 4a, 4c, 4g, and 4h showed promising antimycobacterial activity at a low toxicity level.
Keywords: hetero-Diels-Alder reaction; 4-Thioxo-2-thiazolidinones; Thiopyrano[2,3-d]thiazoles; Anticancer activity; Antimycobacterial activity; Melanoma hetero-Diels-Alder reaction; 4-Thioxo-2-thiazolidinones; Thiopyrano[2,3-d]thiazoles; Anticancer activity; Antimycobacterial activity; Melanoma
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

ATAMANYUK, D.; ZIMENKOVSKY, B.; ATAMANYUK, V.; NEKTEGAYEV, I.; LESYK, R. Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety. Sci. Pharm. 2013, 81, 423-436.

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