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1,4-BIS[3,4-DIHYDRO-2(1H)-QUINOLINON-7-OXY]BUTANE: A CHALLENGE IN SYNTHETIC ROUTES
1,4-BIS[3,4-diHydro-2(1H)-quinolinoN-7-oxy]butane, commonly referred to as Mir121, is a synthetic molecule with potential therapeutic applications for the treatment of neurological disorders.
Mir121 is an analogue of the natural compound, fumitremorgin C, which is derived from the fungus, Fusarium sp.
However, the synthesis of Mir121 presents a challenge in synthetic routes due to its complex molecular structure.
The synthesis of Mir121 involves multiple steps and the use of various reagents and catalysts.
The first step in the synthesis of Mir121 is the condensation of 2-nitropropane and 2,2'-dithiobis(N-ethylacetamido)-N-(2,3-dimethylbut-3-enyl)acetamide, which results in the formation of a key intermediate, 2,2'-dithiobis[N-ethylacetamido]butane.
This intermediate is then transformed into 2,2'-dithiobis[N-ethylacetamido]-N-(2,3-dimethylbut-2-yl)acetamide through a reduction reaction.
The next step in the synthesis of Mir121 involves the condensation of 2,2'-dithiobis[N-ethylacetamido]-N-(2,3-dimethylbut-2-yl)acetamide with 1-[3-(dihydro-imidazo[1,2-d][1,4]benzoxazepin-9-yl)propan-1-yl]-3-ethylurea.
This reaction results in the formation of the third intermediate, 1,4-bis[3,4-diHydro-2(1H)-quinolinoN-7-oxy]butane.
Finally, the synthesis of Mir121 involves the hydrolysis of the third intermediate, 1,4-bis[3,4-diHydro-2(1H)-quinolinoN-7-oxy]butane, to remove the protecting groups.
This step results in the formation of the final product, Mir121.
The complexity of the synthesis of Mir121 has led to the development of various synthetic routes in the chemical industry.
One synthetic route involves the synthesis of 2,2'-dithiobis[N-ethylacetamido]butane, followed by the condensation of this intermediate with 1-[3-(dihydro-imidazo[1,2-d][1,4]benzoxazepin-9-yl)propan-1-yl]-3-ethylurea.
The synthesis of the third intermediate, 1,4-bis[3,4-diHydro-2(1H)-quinolinoN-7-oxy]butane, is then achieved through hydrolysis.
Another synthetic route involves the synthesis of 2,2'-dithiobis[N-ethylacetamido]-N-(2,3-dimethylbut-2-yl)acetamide, followed by the condensation of this intermediate with 1-[3-(dihydro-imidazo[1,2-d][1,4]benzoxazepin-9-yl)propan-1-yl]-3-ethylurea.
The synthesis of the third intermediate, 1,4-bis[3,4-diHydro-2(1H)-quinolinoN-7-oxy]butane, is achieved through hydrolysis, and the final product, Mir121, is obtained through hydrogenation.
Despite the development of various synthetic routes, the synthesis of Mir121 remains a challenge in the chemical industry.
The multiple steps involved, the
