87424-25-7

Usage

Uses

Used in Pharmaceutical Industry:
3-demethylthiocolchicine is used as an antitumor agent for its ability to inhibit cell division and proliferation, making it a potential candidate for the treatment of various types of cancer.
Used in Anti-inflammatory Applications:
3-demethylthiocolchicine is used as an anti-inflammatory agent due to its ability to modulate inflammatory pathways and reduce inflammation in various conditions.
Used in Immunosuppressive Therapy:
3-demethylthiocolchicine is used as an immunosuppressive agent to suppress the immune system, making it useful in the treatment of autoimmune diseases and in preventing organ transplant rejection.

InChI:InChI=1/C21H23NO5S/c1-11(23)22-15-7-5-12-9-17(25)20(26-2)21(27-3)19(12)13-6-8-18(28-4)16(24)10-14(13)15/h6,8-10,15,25H,5,7H2,1-4H3,(H,22,23)/t15-/m0/s1

Upstream product

• 74-93-1 methylthiol 
• 7336-35-8 3-Demethyl-3-acetylcolchicine 
• 7336-33-6 3-demethylcolchicine 
• 5188-07-8 sodium thiomethoxide 
• 51296-12-9 2,3-didemethylthiocolchicine 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 602-41-5 thiocolchicoside 
• 2730-71-4 thiocolchicine 
• 64-86-8 colchicine 

Downstream Products

• 602-41-5 thiocolchicoside 
• 123417-80-1 3-benzoyl-3-demethylthiocolchicine 
• 163956-01-2 3-demethyl-3-(2,3,4,5-tetra-O-acetyl-β-D-glucopyranosyl)thiocolchicine 
• 1256600-75-5 C₄₀H₄₈N₂O₁₀S 
• 939373-74-7 6'-thioacetylthiocolchicoside triacetate 
• 939373-71-4 6'-iodothiocolchicoside triacetate 
• 939373-69-0 6'-tosylthiocolchicoside triacetate 
• 939373-68-9 6'-tosylthiocolchicoside 

Relevant academic research and scientific papers

Antitumor agents. Part 236: Synthesis of water-soluble colchicine derivatives

Water-soluble colchicine derivatives were synthesized from 2-demethylcolchicine and 2-demethylthiocolchicine and evaluated in vitro against human tumor cell replication and for inhibition of tubulin polymerization. The glycinate esters (4, 5) and their ta

METHODS AND USES OF COLCHICINE DERIVATIVES

Colchicine derivative(s), method(s) and use(s) thereof for treatment of inflammation. In certain embodiments, the colchicine derivative is a compound of Formula I: (I)

NOVEL COLCHICINE DERIVATIVES, METHODS AND USES THEREOF

The invention relates to colchicine derivatives, methods and uses thereof for treatment of cancer. In certain embodiments, the colchicine derivative comprises a compound of formula (I), wherein Z is O or S; R1 is selected fro H, a halo group, a substituted or unsubstituted hydrocarbon group, or a substituted or unsubstituted heterogeneous group; R2 and R3 are each independently selected from H, a halo group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic; R is selected from H or a substituted or unsubstituted hydrocarbon group, with the proviso that when R, R2 and R3 are methyl groups, R1 is not -COCH3.

Derivatives of thiocolchicine and its applications to CEM cells treatment using 19F Magnetic Resonance ex vivo

It was shown, that cultured ex vivo human T-Lymphoblastoid (CEM) cells respond to synthesized thiocolchicine and fluorine thiocolchicine derivatives. The preparation of derivatives with substitution at C-3 and C-7 is described. All compounds were used at concentration from 1 nM to 1000 nM. Inhibitory effects of these compounds were examined in the three-dimensional (3-D) culture and cells morphology during treatment was monitored using 9.4 T MRI system. We performed studies of these compounds in CEM cells ex vivo using 1H and 19F Magnetic Resonance Imaging (MRI), 19F Magnetic Resonance Spectroscopy (MRS), High Performance Liquid Chromatography coupled with Ultra Violet (HPLC-UV) and Electron Impact Mass Spectrometry (EIMS). The results of the multi-technique approach are consistent with the fact that the new derivatives are more efficient than colchicine and thiocolchicine ex vivo. Crown Copyright

Tricyclic compounds

Novel tricyclic compounds of formula I as defined in the specification, a process for their preparation and their use for the preparation of optically active or racemic colchicine and thiocolchicine derivatives.

Esters of 3-demethylthiocolchicine and n-acyl analogs

The present invention relates to esters of 3-demethylthiocolchicine and N-acyl analogs thereof having the following formula: STR1 wherein R is O-CO-alkyl, O-CO-CH2 Oalkyl, O-CO-Phenyl, O-COOalkyl; the alkyl group having from 1 to 4 carbon atoms and the Ac group representing acetyl and its higher homologs, benzoyl, alkoxyacetyl, or haloacetyl. The invention further relates to processes for preparing these ester compounds, pharmaceutical compositions thereof and methods for treating diseases such as gout, Mediterranean fever and liver disorders.

PHENOLIC CONGENERS OF COLCHICINE: PREPARATION AND CHARACTERIZATION OF PHENOLIC AND CATECHOLIC ANALOGUES OF COLCHICINE, COLCHICEINE AND THIOCOLCHICINE

Treatment of 2-demethylcolchicine (2) with sulfuric acid afforded 1,2-didemethylcolchicine (6) as the major, and 2,3-didemethylcolchicine (8) as the minor product. 2,3-Didemethylcolchicine (8) was prepared from 3-ethoxycarbonyl-3-demethylcolchicine by sulfuric acid treatment.Hydrolysis of catecholic compounds 6 and 8 with 0.1 N hydrochloric acid afforded colchiceines 13 and 14, respectively.Ester derivatives of 2-demethyl- and 3-demethylcolchicine, and of catechols 6 and 8 were prepared.A direct conversion of 3 into 3-demethylthiocolchicine (15) and conversion of 15 into ester derivatives is described.Cleavage of the ether groups of colchicine by boron tribromide is also reported.

Antiinflammatory 2,3-didemethylcolchicine and additional derivatives

The present invention describes the finding of potent antiinflammatory properties in 2,3-didemethylcolchicine and its analogs.

SELECTIVE ETHER-CLEAVAGE OF THIOCOLCHICOSIDE AND THIOCOLCHICINE: CHARACTERIZATION OF 3- AND 2-DIMETHYLTHIOCOLCHICINE AND CATECHOLIC CONGENERS

Selective ether cleavage in the thiocolchicine series took a similar course as observed in the colchicine series.Thiocolchicoside (2) afforded with phosphoric acid, the known 3-demethylthiocolchicine (6), and thiocolchicine (1) gave with conc. sulfuric acid at 70 deg C, a mixture of the 2-demethylthiocolchicine (3) and the catechols 4 and 5.