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Open AccessArticle

Synthesis and Antiproliferative Screening Of Novel Analogs of Regioselectively Demethylated Colchicine and Thiocolchicine

1
Department of Medical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznan, Poland
2
Department of Materials Chemistry, Faculty of Chemistry Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland
3
Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Rudolfa Weigla 12, 53-114 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Qiao-Hong Chen
Molecules 2020, 25(5), 1180; https://doi.org/10.3390/molecules25051180
Received: 29 January 2020 / Revised: 2 March 2020 / Accepted: 3 March 2020 / Published: 5 March 2020
(This article belongs to the Special Issue Anticancer Agents: Design, Synthesis and Evaluation)
Colchicine, a pseudoalkaloid isolated from Colchicum autumnale, has been identified as a potent anticancer agent because of its strong antimitotic activity. It was shown that colchicine modifications by regioselective demethylation affected its biological properties. For demethylated colchicine analogs, 10-demethylcolchicine (colchiceine, 1) and 1-demethylthiocolchicine (3), a series of 12 colchicine derivatives including 5 novel esters (2bc and 4bd) and 4 carbonates (2ef and 4ef) were synthesized. The antiproliferative activity assay, together with in silico evaluation of physicochemical properties, confirmed attractive biological profiles for all obtained compounds. The substitutions of H-donor and H-acceptor sites at C1 in thiocolchicine position provide an efficient control of the hydration affinity and solubility, as demonstrated for anhydrate 3, hemihydrate 4e and monohydrate 4a. View Full-Text
Keywords: colchicine analogs; thiocolchicine; colchiceine; antimitotic agents; antiproliferative activity; hydrates colchicine analogs; thiocolchicine; colchiceine; antimitotic agents; antiproliferative activity; hydrates
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MDPI and ACS Style

Czerwonka, D.; Sobczak, S.; Maj, E.; Wietrzyk, J.; Katrusiak, A.; Huczyński, A. Synthesis and Antiproliferative Screening Of Novel Analogs of Regioselectively Demethylated Colchicine and Thiocolchicine. Molecules 2020, 25, 1180.

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