N-Deacetylcolchicine

Base Information

• Chemical Name: N-Deacetylcolchicine
• CAS No.: 3476-50-4
• Molecular Formula: C20H23 N O5
• Molecular Weight: 357.406
• Hs Code.: 2922509090
• UNII: 2IAP3WIO1P
• DSSTox Substance ID: DTXSID601150161
• Nikkaji Number: J55.416B
• Wikidata: Q27149718
• ChEMBL ID: CHEMBL1063
• Mol file: 3476-50-4.mol

Synonyms:deacetylcolchicine;desacetylcolchicine;N-deacetylcolchiceine;NSC-36354;trimethylcolchicinic acid methyl ether;trimethylcolchicinic acid methyl ether tartrate (1:1), ((S)-(R-(R*,R*)))-isomer;trimethylcolchicinic acid methyl ether tartrate (2:1), ((S)-(R-(R*,R*)))-isomer;trimethylcolchicinic acid methyl ether tartrate, ((S)-(R-(R*,R*)))-isomer

Chemical Property of N-Deacetylcolchicine

Chemical Property:

• Vapor Pressure: 1.29E-15mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 626.6°Cat760mmHg
• PKA: 8.62±0.40(Predicted)
• Flash Point: 287°C
• PSA: 80.01000
• Density: 1.25g/cm³
• LogP: 3.39450
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 357.15762283
• Heavy Atom Count: 26
• Complexity: 638

Purity/Quality:

99% ^*data from raw suppliers

(S)-N-DeacetylColchicine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C2C(=CC1=O)C(CCC3=CC(=C(C(=C32)OC)OC)OC)N
• Isomeric SMILES: COC1=CC=C2C(=CC1=O)[C@H](CCC3=CC(=C(C(=C32)OC)OC)OC)N
• 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.

Technology Process of N-Deacetylcolchicine

There total 4 articles about N-Deacetylcolchicine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 51.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + trimethylcolchicinic acid (3482-37-9,2731-31-9) → deacetylcolchicine (3476-50-4) + (-)-N-deacetylisocolchicine (47477-04-3)

Guidance literature:

In diethyl ether; dichloromethane;

DOI:10.1071/CH9921577

Reference yield: 39.0%

→ colchicine (64-86-8,54192-66-4) + deacetylcolchicine (3476-50-4)

Guidance literature:

Reference yield:

Benzyloxycarbonyl-L-phenylalanyl-L-lysyl-PABC-deacetylcolchicine (1279111-08-8) → deacetylcolchicine (3476-50-4) + Cbz-L-Phe-L-Lys-OH (71448-16-3)

Guidance literature:

With bovine spleen cathepsin B; at 37 ℃; pH=5; aq. buffer; Enzymatic reaction;

DOI:10.1021/ml100287y

upstream raw materials:

diazomethane

trimethylcolchicinic acid

Benzyloxycarbonyl-L-phenylalanyl-L-lysyl-PABC-deacetylcolchicine

C₅₅H₆₁N₅O₁₃

Downstream raw materials:

Benzyloxycarbonyl-L-phenylalanyl-L-lysyl-PABC-deacetylcolchicine

C₅₅H₆₁N₅O₁₃

N-(phenoxyacetyl)deacetylcolchicine

N-methyldemecolcine

Refernces

• 1、 -. "5,6,7,9-tetrahydro-1,2,3-trimethoxy-9-oxobenzo[alpha]heptalene derivative and pharmaceutical use". . . Retrieved 2008/06/13.
• 2、 Hufford,Capraro,Brossi. "13C and 1H-NMR assignments for colchicine derivatives". . p. 50 - 56. Retrieved 2007/10/06.