(R/S)-N-Deacetyl Colchiceine

Base Information

• Chemical Name: (R/S)-N-Deacetyl Colchiceine
• CAS No.: 68296-64-0
• Molecular Formula: C₁₉H₂₁NO₅
• Molecular Weight: 343.379
• Mol file: 68296-64-0.mol

Synonyms:(R/S)-N-Deacetyl Colchiceine;(+/-)-Deacetylisocolchiceine;(+/-)-N-Deacetylisocolchiceine;7-AMino-6,7-dihydro-9-hydroxy-1,2,3-triMethoxy-benzo[a]heptalen-10(5H)-one

Chemical Property of (R/S)-N-Deacetyl Colchiceine

Chemical Property:

• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

97% ^*data from raw suppliers

(R/S)-N-DeacetylColchiceine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R/S)-N-Deacetyl Colchiceine

There total 24 articles about (R/S)-N-Deacetyl Colchiceine 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: 72.0%

N-tert-butoxycarbonyldesacetylisocolchicine (73276-20-7) → 7-amino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one (73307-44-5,68296-64-0)

Guidance literature:

With hydrogenchloride; at 110 ℃; for 1.5h;

DOI:10.1021/ja00409a032

Reference yield: 50.0%

N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl) acetamide (209810-38-8,54192-66-4) → 7-amino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one (73307-44-5,68296-64-0)

Guidance literature:

With sulfuric acid; In acetic acid; at 80 - 90 ℃; for 5h;

DOI:10.1021/jo00363a021

Reference yield:

3,4,5-trimethoxycinnamic acid (90-50-6) → 7-amino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one (73307-44-5,68296-64-0)

Guidance literature:

Multi-step reaction with 11 steps

1: oxalyl chloride / benzene / 3 h / Ambient temperature

2: 70 percent / N,N-dimethylaniline / diethyl ether / 14 h / Heating

3: 68 percent / 1.) sodium hydride / dimethylsulfoxide / 2.) 55 deg C, 2 h

4: 72 percent / hydrogen / 5percent Pd-C / methanol / 48 h / 2585.7 Torr

5: 1.) lithium diisopropylamide / tetrahydrofuran / 1.) -65 deg C, 65 min, 2.) -60 deg C, 15 min; -60 - 10 deg C, 30 min

6: oxalic acid / tetrahydrofuran; H₂O / 4 h / Ambient temperature

7: 1.) boron trifluoride etherate, 2.) trifluoroacetic acid / 1.) nitromethane, room temperature, 5 min, 2.) 20 min

8: 28 percent / benzene / 0.33 h / Heating

10: 54 percent / diphenylphosphoryl azide, triethylamine / 17 h / Heating

11: 72 percent / aq. hydrochloric acid / 1.5 h / 110 °C

With hydrogenchloride; oxalyl dichloride; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; hydrogen; oxalic acid; sodium hydride; N,N-dimethyl-aniline; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide; benzene;

DOI:10.1021/ja00409a032

upstream raw materials:

(S)-7-((Ξ)-benzylidenamino)-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one

N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl) acetamide

N-tert-butoxycarbonyldesacetylisocolchicine

(+/-)-7,9-diamino-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-10-one

Downstream raw materials:

trimethylcolchicinic acid

(+)-N-deacetylcolchiceine

(+/-)-N-(trifluoroacetyl)deacetylcolchiceine

(+/-)-N-deacetylcolchicine

Refernces

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

10.1071/CH9921577

The study investigates the synthesis, structural characterization, and tubulin-binding properties of two ketone derivatives of colchicine, namely 7-oxodeacetamidocolchicine (2) and 7-oxodeacetamidoisocolchicine (3). The researchers converted commercially available (-)-colchicine (1) into these ketones via deacetylcolchiceine (4) as an intermediate. The primary goal was to develop a reliable synthetic route for these compounds, which are of interest due to their potential for enantioselective reduction studies and their biological properties. The study also explores the X-ray crystal structures of compounds (2) and (3) to understand their molecular conformations and how they interact with tubulin. Additionally, the tubulin-binding properties of these ketones were evaluated to assess their potential as antitumor agents. The results showed that while compound (2) exhibited significant inhibitory effects on tubulin polymerization, compound (3) had little effect, highlighting the importance of molecular structure in biological activity.

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