3476-50-4

Basic information

• Product Name: trimethylcolchicinic acid methyl ether
• Synonyms: trimethylcolchicinic acid methyl ether;(S)-7-Amino-6,7-dihydro-1,2,3,10-tetramethoxybenzo[a]heptalen-9(5H)-one;Deacetylcolchicine;Desacetylcolchicine;(S)-N-Deacetyl Colchicine;(-)-7-Deacetylcolchicine;(7S)-7-AMino-6,7-dihydro-1,2,3,10-tetraMethoxy-benzo[a]heptalen-9(5H)-one;NSC 201400
• CAS NO: 3476-50-4
• Molecular Formula: C₂₀H₂₃NO₅
• Molecular Weight: 357.44
• Product Categories: Amines;Chiral Reagents;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Chiral Reagents, Heterocycles, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 3476-50-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 490.03°C (rough estimate)
• Flash Point: 287°C
• Appearance: /
• Density: 1.2532 (rough estimate)
• Vapor Pressure: 1.29E-15mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• PKA: 8.62±0.40(Predicted)
• CAS DataBase Reference: trimethylcolchicinic acid methyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: trimethylcolchicinic acid methyl ether(3476-50-4)
• EPA Substance Registry System: trimethylcolchicinic acid methyl ether(3476-50-4)

Safety Data

• Hazardous Substances Data: 3476-50-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

An antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pathway.

InChI:InChI=1/C20H23NO5/c1-23-16-8-6-12-13(10-15(16)22)14(21)7-5-11-9-17(24-2)19(25-3)20(26-4)18(11)12/h6,8-10,14H,5,7,21H2,1-4H3/t14-/m0/s1

Upstream product

• 1279111-11-3 C₅₅H₆₁N₅O₁₃ 
• 1279111-08-8 Benzyloxycarbonyl-L-phenylalanyl-L-lysyl-PABC-deacetylcolchicine 
• 186581-53-3 diazomethane 
• 3482-37-9 trimethylcolchicinic acid 

Downstream Products

• 7336-44-9 N-methyldemecolcine 
• 7411-12-3 N-deacetyl-N-formylcolchicine 
• 86436-38-6 N-pivloyldeacetylcolchicine 
• 99481-33-1 N-crotonyldeacetylcolchicine 
• 26279-89-0 2-chloro-N-{(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl}acetamide 
• 1279111-08-8 Benzyloxycarbonyl-L-phenylalanyl-L-lysyl-PABC-deacetylcolchicine 
• 1279111-11-3 C₅₅H₆₁N₅O₁₃ 
• 1338797-77-5 N-(7-cyclohexyloxy-7-oxoheptanoyl)-N-deacetylcolchicine 
• 1338797-80-0 N-(7-phenyloxy-7-oxoheptanoyl)-N-deacetylcolchicine 
• 1338797-59-3 3-tert-butyl 5-[12-oxo-12-(N-deacetylcolchicin-7-N-yl)dodecyl] (4S,5R)-2-(4-methoxyphenyl)-4-phenyl-oxazolidine-3,5-dicarboxylate 
• 1338797-60-6 (2R,3S)-N-(tert-butoxycarbonyl)phenylisoserine 12-oxo-12-(N-deacetylcolchicin-7-N-yl)dodecyl ester 
• 1391054-50-4 C₆₅H₉₁N₇O₂₁ 
• 1391054-42-4 4-{3'-[3,5-di(4-methoxybenzylamino)-2,4,6-triazinylamino]ethyloxy-3'-oxopropyl}-1-{3'-[(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)amino]-3'-oxopropyl}-1,2,3-triazole 
• 1391054-43-5 4-{5'-[3,5-di(4-methoxybenzylamino)-2,4,6-triazinylamino]ethyloxy-5'-oxopentyl}-1-{3'-[(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)amino]-3'-oxopropyl}-1,2,3-triazole 

Relevant articles and documents

Design, synthesis, and antitumor activity of 4-halocolchicines and their pro-drugs activated by cathepsin B

Novel colchicine derivatives possessing various substituents at the C4 position were prepared. Among them, 4-halo derivatives 3-6 were found to exhibit higher activity against cancer cell lines (A549, HT29, HCT116) as well as on mice transplanted with the HCT116 human colorectal carcinoma cell line than colchicine (1). Further, utilizing the 4-substituted colchicines, we prepared pro-drugs having a dipeptide side chain and demonstrated that these pro-drugs were activated by cathepsin B, an enzyme overexpressed in tumor cells, and exhibited selective toxicity to the tumor cells.

Semisyntheses, X-Ray Crystal Structures and Tubulin-Binding Properties of 7-Oxodeacetamidocolchicine and 7-Oxodeacetamidoisocolchicine

Commercially available (-)-colchicine (1) has been converted, via deacetylcolchiceine (4), into a mixture of 7-oxodeacetamidocolchicine (2) and 7-oxodeacetamidoisocolchicine (3).The X-ray structures and tubulin-binding properties of these title ketones are described.