54192-66-4

Usage

Uses

Used in Pharmaceutical Industry:
(+-)-Colchicine is used as an anti-inflammatory and antimitotic agent for its ability to inhibit cell division and reduce inflammation. It is particularly effective in treating gout and certain autoimmune diseases, such as Familial Mediterranean Fever and Beh?et's disease.
Used in Cancer Treatment:
(+-)-Colchicine is used as a chemotherapeutic agent for its potential to disrupt microtubule dynamics, which can lead to cell cycle arrest and apoptosis in cancer cells. It has shown promise in the treatment of various types of cancer, including breast, ovarian, and multiple myeloma.
Used in Drug Delivery Systems:
(+-)-Colchicine can be used as a component in drug delivery systems to improve its bioavailability, targeting, and therapeutic efficacy. By incorporating (+-)-Colchicine into nanoparticles or other drug carriers, it can be more effectively delivered to specific cells or tissues, reducing side effects and enhancing treatment outcomes.
Used in Research Applications:
(+-)-Colchicine is used as a research tool for studying the mechanisms of cell division, inflammation, and cancer progression. Its antimitotic properties make it a valuable compound for investigating the role of microtubules in cellular processes and for identifying potential targets for new therapeutic interventions.

Upstream product

• 186581-53-3 diazomethane 
• 102491-69-0 (+/-)-colchiceine 
• 102491-73-6 (+/-)-N-deacetylcolchicine 
• 108-24-7 acetic anhydride 
• 60-29-7 diethyl ether 
• 67-66-3 chloroform 
• 477-27-0 colchiceine 
• 33530-04-0 2,10-didemethylcolchicine 
• 133946-39-1 <1-3H>-3-phenylprop-2-enal 
• 131946-50-4 <3-14C>-3-phenylpropionic acid 
• 186374-95-8 (S)-tert-butyl N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalene-7-yl)carbamate 
• 947620-01-1 C₂₈H₃₁N₃O₇ 
• 102419-91-0 (+)-N-deacetylcolchicine 
• 477-27-0 (+)-colchiceine 

Downstream Products

• 73307-44-5 7-amino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one 
• 55340-40-4 10-hydroxyethylamino-10-demethoxycolchicine 
• 55340-44-8 10--10-demethoxycolchicine 
• 47477-04-3 (-)-N-deacetylisocolchicine 
• 75520-89-7 (+)-colchicine 
• 75491-24-6 10-ethoxy-10-demethoxycolchicine 
• 75488-69-6 Ethyl isocolchicinate 
• 67620-24-0 10-ethylcolchiceinamide 
• 6962-03-4 10-(diethylamino)colchicine 
• 76129-12-9 10-benzylthiocolchicine 
• 2826-80-4 N-methyl colchiceinamide 
• 55511-34-7 N-[(7S)-5,6,7,9-tetrahydro-1,2,3-trimethoxy-10-(ethylthio)-9-oxobenzo[a]heptalen-7-yl]acetamide 
• 61014-70-8 (-)-10,11-oxy-10,12a-cyclo-10,11-secocolchicine 
• 7336-36-9 2-demethylcolchicine 

Relevant academic research and scientific papers

Asymmetric Total Syntheses of Colchicine, β-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME)

A concise and highly enantioselective synthesis of colchicine (>99% ee) in eight steps and 9.3% overall yield, without the need for protecting groups, was developed. A unique Wacker oxidation was used for enabling regioselective construction of the highly oxidized and synthetic challenging tropolone C-ring. Furthermore, asymmetric syntheses of β-lumicolchicine and N-acetylcolchinol-O-methyl ether (NCME) were achieved. Notably, NCME was synthesized from β-lumicolchicine by an unusual decarbonylation and electrocyclic ring-opening cascade reaction.

Gram-Scale, Seven-Step Total Synthesis of (-)-Colchicine

Herein we report a streamlined, gram-scale total synthesis of (-)-colchicine that takes only 7 easy steps, with an overall yield of 27-36%. To warrant the synthetic efficiency and practicality of (-)-colchicine, we tactically utilized a modified version of a powerful Ir-catalyzed amidation reported by Carreira to install the key chiral C-7 acetamido group, Suzuki and biomimetic phenol oxidative coupling, and Banwell-inspired cyclopropane ring cleavage to construct (-)-colchicine precisely and rapidly. Remarkably, a described strategy also can shorten the synthesis of allocolchicinoid to 4 steps.

Syntheses and biological evaluation of ring-C modified colchicine analogs

Ring-C modified alkaloids were synthesized from colchicine using iminonitroso Diels-Alder reactions in a highly regio- and stereoselective fashion. Several analogs exhibited cytotoxic activity similar to that of colchicine itself against PC-3 and MCF-7 cancer cell lines, by serving as prodrugs of colchicine through retro Diels-Alder reactions under the assayed conditions. In vitro microtubule polymerization assays indicated that these modifications affected their interaction with tubulin.

SEMISYNTHETIC PROCESS FOR THE PREPARATION OF COLCHICINE

The invention relates to a process for the preparation of colchicine 1 from colchicoside 2 which comprises enzymatic conversion of colchicoside 2 to 3-O- demethylcolchicine 3, wherein the enzyme used is a cellulase. According to another aspect of the invention, 3-O-demethylcolchicine 3 can be converted to colchicine 1 using an alkylating agent. The invention also relates to a process for enriching the colchicine 1 content of extracts from plants belonging to the Colchicaceae family containing colchicine 1, colchicoside 2 and 3 -(9-demethyl colchicine 3, which comprises conversion by means of a colchicoside 2 cellulase to 3-O-demethylcolchicine 3, followed by conversion of 3-O-demethylcolchicine 3 to colchicine 1 using an alkylating agent.

Asymmetric synthesis method of colchicine and allocolchicine

The invention provides an asymmetric synthesis method of colchicine and allocolchicine, and belongs to the field of chemical synthesis. According to the invention, cheap commercial isovanillin A is used as a raw material, asymmetric allyl amination catalyzed by metal Ir is taken as a key reaction, a cyclization precursor E is obtained through Suzuki coupling reaction with a halide D, allocolchicine F is rapidly synthesized through intramolecular oxidative coupling, and finally, efficient asymmetric synthesis of colchicine I is completed through a bionic cyclopropane ring-opening strategy. Thesynthesis strategy used in the invention is simple and economic, good in operability and short in time consumption, and can meet the requirements of new drug development and large-scale preparation.

Enantioselective total synthesis of (-)-colchicine, (+)-demecolcinone and metacolchicine: Determination of the absolute configurations of the latter two alkaloids

Here, we describe a concise, enantioselective, and scalable synthesis of (-)-colchicine (9.2% overall yield, >99% ee). Moreover, we have also achieved the first syntheses of (+)-demecolcinone and metacolchicine, and determined their absolute configurations. The challenging tricyclic 6-7-7 core of colchicinoids was efficiently introduced using an intramolecular oxidopyrylium-mediated [5 + 2] cycloaddition reaction. Notably, the synthesized colchicinoid 23 exhibited potent inhibitory activity toward the cell growth of human cancer cell lines (IC50 = ～3.0 nM), and greater inhibitory activity towards microtubule assembly than colchicine, making it a promising lead in the search for novel anticancer agents.

Synthesis method of colchicine

The invention relates to a synthesis method of colchicine. According to the synthesis method of the colchicine, a compound as shown in the specification is used as a raw material, and then efficient intramolecular [5+2] cycloaddition is considered as key reaction; in combination with locating group guided dehydrogenation Hike reaction and Walker reaction, a molecular skeleton structure is rapidly constructed, so that an obtained structural formula, which has the same structure as a natural product, is the colchicine; and a modification research can be carried out on the colchicine favorably, so as to improve the bioactivity and the toxic and side effects of the colchicine.

Total synthesis of (-)-colchicine via a Rh-triggered cycloaddition cascade

(Chemical Equation Presented) A synthesis of the antimitotic alkaloids (-)-colchicine and (-)-isocolchicine is reported. Important steps are (a) enantioselective transfer-hydrogenation of an alkynone, (b) iodine/magnesium exchange with subsequent aromatic

Total synthesis of (-)-colchicine by an oxyallyl [4 + 3] cycloaddition

An enantioselective synthesis of (-)-colchicine, free from isocolchicine, is delineated and features tandem application of the intramolecular Diels-Alder reaction of acetylene-tethered oxazoles and the [4+3] cycloaddition of oxyallyls. This work underscores the synthetic utility of little explored α-alkoxy substituted oxyallyls. (C) 2000 Elsevier Science Ltd.