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Article

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.
Sci. Pharm. 2013, 81(2), 423-436; https://doi.org/10.3797/scipharm.1301-13
Submission received: 14 January 2013 / Accepted: 4 February 2013 / Published: 4 February 2013

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

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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. https://doi.org/10.3797/scipharm.1301-13

AMA 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. Scientia Pharmaceutica. 2013; 81(2):423-436. https://doi.org/10.3797/scipharm.1301-13

Chicago/Turabian Style

ATAMANYUK, Dmytro, Borys ZIMENKOVSKY, Vasyl ATAMANYUK, Ihor NEKTEGAYEV, and Roman LESYK. 2013. "Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety" Scientia Pharmaceutica 81, no. 2: 423-436. https://doi.org/10.3797/scipharm.1301-13

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