Synthesis and Antitumor Activity of New 5-Ylidene Derivatives of 3-(Furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-
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hesis and Antitumor Activity of New 5-Ylidene Derivatives of 3-(Furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one V. Ya. Horishnya and V. S. Matiychukb,* a
Danilo Halytsky Lviv National Medical University, Lviv, 79010 Ukraine b
Ivan Franko Lviv National University, Lviv, 79005 Ukraine *e-mail: [email protected]
Received May 31, 2020; revised June 6, 2020; accepted June 11, 2020
Abstract—Reactions of 3-(furan-2-ylmethyl)-2-sulfanyidene-1,3-thiazolidin-4-one with aromatic and heterocyclic aldehydes afforded a series of previously unknown 5-[(het)arylmethylidene]-3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-ones. Treatment of 3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one with thionyl chloride gave in a good yield 3,3′-bis(furan-2-ylmethyl)-2,2′-disulfanylidene-5,5′-bi-1,3-thiazolidinylidene-4,4′-dione which was reduced with zinc in acetic acid to 3,3′-bis(furan-2-ylmethyl)-2,2′-disulfanylidene-5,5′-bi-1,3-thiazolidine-4,4′-dione. The synthesized compounds were screened for antitumor activity. Keywords: rhodanine, 2-sulfanylidene-1,3-thiazolidin-4-one, furan, thionyl chloride, antitumor activity
DOI: 10.1134/S107042802009016X Design of highly efficient and low-toxic medicines and their implementation into medical practice constitute one of the most important problems of organic and medicinal chemistry. The results of recent studies of the chemistry and biological activity of rhodanine (2-sulfanylidene-1,3-thiazolidin-4-one) derivatives convincingly showed that compounds of this series are promising as pharmacological agents with a broad spectrum of activity. Lead compounds exhibiting antimicrobial, antitubercular, antiviral, antidiabetic, antiinflammatory, antitumor, anticonvulsant, and other activities have been identified among rhodanine derivatives. Therefore, rhodanine fragment is considered a privileged structure in medicinal chemistry [1–3]. On the other hand, furan compounds have found applications in various fields of chemistry and technology, in particular in pharmacy, due to their unique physicochemical, chemical, and biological properties [4–6]. First of all, a broad range of biological activity of natural and synthetic furan compounds, as well as of its fused derivatives (benzofuran, naphthofurans, anthrafurans, etc.), should be noted. In view of the above stated, there is great interest in the use of furan heterocycle as an important building block in the design of medicines. The present study continues our previous works related to the design of biologically active nitrogen
heterocycles [7–20]. It was aimed at synthesizing 5-ylidene derivatives of 3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one and evaluating them for antitumor activity. Compounds exhibiting valuable chemotherapeutic properties such as antiviral [21–23], antifungal [24], trypanocidal [25, 26], and antitumor activities [27–29] have already been found among this series. The target 5-ylidene-3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-ones 4a–4k were synthesized by reacting 3-(furan-2-
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