55511-34-7Relevant academic research and scientific papers
7-Deacetyl-10-alkylthiocolchicine derivatives-new compounds with potent anticancer and fungicidal activity
Kurek, Joanna,Kwa?niewska-Sip, Patrycja,Myszkowski, Krzysztof,Cofta, Grzegorz,Murias, Marek,Barczyński, Piotr,Jasiewicz, Beata,Kurczab, Rafa?
, p. 1708 - 1714 (2018/10/26)
A series of new semi-synthetic 7-deacetyl-10-alkylthiocolchicne derivatives with ethyl, n-propyl, i-propyl and n-butyl substituents were synthesised and characterised by spectroscopic methods, elemental analysis, DFT calculations and molecular docking simulations. All the synthesized compounds have been tested for fungicidal and anticancer activities against SKOV-3, LoVo, MCF-7, MDA-MB-231 and the lung-derived fibroblast CCD39Lu. All the new colchicine derivatives exhibit significantly higher cytotoxicity towards the SKOV-3 tumour cell line than the natural product-colchicine. The most effective cytotoxic agents were 7-deacetyl-10-n-buthylthiocolchicine and 7-deacetyl-10-i-propylthiocolchicine. Among all the compounds tested, 7-deacetyl-10-n-buthylthiocolchicine exhibited the highest fungicidal activity. Molecular modeling indicated that several mutations found in the β-tubulin unit of the tested fungal strains are crucial for antifungal activity and selectivity of 7-deacetyl-10-n-buthylthiocolchicine. The obtained results may be useful for the development of selective colchicine derivatives as effective fungicidal and/or anticancer drugs.
Synthesis of sulfur containing colchicine derivatives and their biological evaluation as cytotoxic agents
Kurek, Joanna,Boczon, Wladyslaw,Myszkowski, Krzysztof,Murias, Marek,Borowiak, Teresa,Wolska, Irena
, p. 279 - 289 (2014/03/21)
Semi-synthetic C-10 alkyl thio analogues of the cytotoxic natural alkaloid colchicine have been found to exhibit cytotoxicity towards tumour cell lines at levels comparable to that of the natural product. An efficient synthesis of 10-alkyl thiocolchicines in mild conditions is proposed and the products are studied by 1H and 13C NMR, FT-IR, MS-EI methods and elementary analysis. The crystal structure of 10-ethylthiocolchicine is characterised using X-ray diffraction methods. Cytotoxic activity against selected cancer cell lines for all obtained 10-alkylthio analogues of colchicine is also reported.
Alkylthiocolchicines and N deacetyl alkylthiocolchicines and their antileukemic activity
Shiau,De,Harmon
, p. 646 - 648 (2007/10/06)
A series of alkylthiocolchicines (methyl, ethyl, n butyl, n hexyl, n octyl and pinanyl) was prepared from cholchicine by treatment with the appropriate alkyl mercaptan and p toluene sulfonic acid. Some of these compounds (methyl, ethyl, and n butylthiocolchicines) were deacetylated in good yields with 2 N hydrochloric acid in methanol. These compounds were tested for their antileukemic activity in an in vitro assay against L 1210 (mouse leukemia). Preliminary results showed that methylthiocolchicine is more active and the other alkylthiocolchicines are much less active than colchicine. N deacetyl methylthiocolchicine is as active as colchicine.
