7-O-DeMethyl α-Narcotine

Base Information

• Chemical Name: 7-O-DeMethyl α-Narcotine
• CAS No.: 68353-55-9
• Molecular Formula: C21H21NO7
• Molecular Weight: 399.4
• Mol file: 68353-55-9.mol

Synonyms:7-O-DeMethyl α-Narcotine

Chemical Property of 7-O-DeMethyl α-Narcotine

Chemical Property:

• PSA: 86.69000
• LogP: 2.51670
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Dichloromethane (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

7-O-Demethylα-Narcotine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 7-O-Demethyl α-Narcotine, is a derivative of Narcotine (N378890), a noscapinoid class of microtubule binding compounds that alter microtubule dynamics without affecting tubulin polymer mass. Noscapinoids show great promise as chemotherapeutic agents for the treatment of human cancers. Unlike Narcotine, (-)-α-Narcotinediol deos not inhibit small-intestinal transport in rats.

Technology Process of 7-O-DeMethyl α-Narcotine

There total 4 articles about 7-O-DeMethyl α-Narcotine 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: 78.0%

noscapine (128-62-1) → (S)-7-hydroxy-6-methoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo-[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one (68353-55-9)

Guidance literature:

With sodium azide; sodium iodide; In N,N-dimethyl-formamide; at 140 ℃; for 4h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.bcp.2011.03.029

Reference yield:

5-methoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydro-isobenzofuran-4-yl (851983-58-9) + benzylamine (100-46-9) → 7-benzylamino-6-methoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one (870190-27-5) + (S)-7-hydroxy-6-methoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo-[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one (68353-55-9)

Guidance literature:

With barium dihydroxide; 2-(2^'-di-tert-butylphosphine)biphenylpalladium(II) acetate; α,α,α-trifluorotoluene; In water; at 110 ℃; for 0.25h;

DOI:10.1021/jm050674q

Reference yield:

(S)-7-tert-butoxy-6-methoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one (68353-58-2) → (S)-7-hydroxy-6-methoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo-[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one (68353-55-9)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 12h;

DOI:10.1002/ardp.19783110804

upstream raw materials:

(S)-7-tert-butoxy-6-methoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one

noscapine

5-methoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydro-isobenzofuran-4-yl

benzylamine

Downstream raw materials:

(S)-5-methoxy-1-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydroisobenzofuran-4-yl benzylcarbamate

(S)-5-methoxy-1-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3-oxo-1,3-dihydroisobenzofuran-4-yl benzoate

7-benzylamino-6-methoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one

noscapine

Refernces

• 1、 Anderson, James T.,Ting, Anthony E.,Boozer, Sherry,Brunden, Kurt R.,Danzig, Joel,Dent, Tom,Harrington, John J.,Murphy, Steven M.,Perry, Rob,Raber, Amy,Rundlett, Stephen E.,Wang, Jianmin,Wang, Nancy,Bennani, Youssef L.. "Discovery of S-phase arresting agents derived from noscapine". . p. 2756 - 2758. Retrieved 2005.
• 2、 -. "SYNTHESIS AND CHARACTERIZATION OF SECOND GENERATION BENZOFURANONE RING SUBSTITUTED NOSCAPINE ANALOGS". Page/Page column 60. . Retrieved 2013/02/27.