1950-39-6

Usage

Uses

Used in Pharmaceutical Development:
N'-[5-[[4-[[5-(acetylhydroamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxysuccinamide monohydrochloride is used as a building block for the synthesis of new pharmaceuticals due to its ability to form multiple chemical bonds with biological targets, which can enhance the compound's interaction with specific receptors or enzymes in the body.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxysuccinamide monohydrochloride serves as a subject of study for understanding its specific properties, such as its reactivity, stability, and potential interactions with biological systems. This research can lead to insights that inform the design of more effective drugs.
Used in Drug Delivery Systems:
N'-[5-[[4-[[5-(acetylhydroamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxysuccinamide monohydrochloride may be utilized in the development of drug delivery systems to improve the bioavailability and targeting of therapeutic agents, taking advantage of its functional groups to facilitate attachment to drug carriers or to enhance the compound's solubility and stability.
Used in Biochemical Assays and Diagnostics:
N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxysuccinamide monohydrochloride's reactivity and functional groups may also find applications in biochemical assays and diagnostic tools, where it could be used to detect or measure the presence of specific biological molecules, leveraging its ability to form stable bonds with target analytes.

Upstream product

• 112139-65-8 N'-<5-<<4-<<5-pentyl>amino>-1,4-dioxobutyl>(phenylmethoxy)amino>pentyl>-N-(4-cyanobutyl)-N-(phenylmethoxy)butanediamide 
• 112139-60-3 N-(4-Cyanobutyl)-N-(benzyloxy)succinamic Acid 
• 83966-23-8 1-Amino-5-pentane 
• 112139-63-6 N-(4-cyanobutyl)-3-<<5-<(benzyloxy)acetylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid 
• 112139-64-7 N-(5-aminopentyl)-3-<<5-<(benzyloxy)acetylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid 
• 112139-61-4 N-(4-cyanobutyl)-N-(benzyloxy)acetamide 
• 112139-59-0 O-benzyl-N-(4-cyanobutyl)-hydroxylamine 

Downstream Products

• 84211-47-2 N-Succinyl-desferri-ferrioxyamin B 

Relevant academic research and scientific papers

Multistage process for the preparation of highly pure deferoxamine mesylate salt

The present invention provides a purification process whereby deferoxamine B produced by a microorganism and in mixture with other polyhydroxamates produced by the microorganism may be converted into its mesylate salt substantially free of the other polyhydroxamates and substantially free of chloride ion. The process includes adsorption and desorption of the deferoxamine B on an adsorption resin, direct precipitation of the deferoxamine free base out of the eluent from the adsorption resin, contacting of the deferoxamine B free base with methanesulfonic acid and isolation of the deferoxamine B mesylate salt by precipitation. This process minimizes decomposition of deferoxamine B.

A versatile synthesis of deferrioxamine B

A new and versatile route to N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]-hydrox yamino]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide, deferrioxamine B (DFO), is described. The key improvement over the two prior routes was replacement of the nitrile in 2 with a tert-butoxycarbonyl-protected amino terminus. Elimination of the nitrile improved the kinetics of hydrogenation in that the benzyl groups of 12 were cleaved more rapidly than saturation of the cyano group of 2, and a potential overreduction byproduct (4) was thus avoided. N-(Benzyloxy)-1,5-diaminopentane (6) was selectively protected at the primary amino site with a tert-butoxycarbonyl (BOC) group, providing 7. This was reacted at the (benzyloxy)amine with succinic anhydride to produce carboxylic acid 8, which was in turn acylated regiospecifically with diamine 6 at the primary amine to give (benzyloxy)amine 9. The previous two steps were reiterated to afford DFO reagent 11. This synthon allows for modification of DFO at either end of the molecule, thus providing more flexibility in accessing DFO analogues than any prior route. Acetylation of 11, followed by hydrogenolysis and tert-butoxycarbonyl group removal, furnished DFO.

Method for the synthesis of desferrioxamine B and analogs thereof

Disclosed is a synthesis of desferrioxamine B and analogs and homologs thereof beginning with the generation of the O-protected N-(4-cyanobutyl)hydroxylamine which is acylated at the O-benzylhydroxylamine nitrogen with either succinic or acetic anhydride. The resulting half-acid amide or amide respectively, is subjected to a series of high yield condensations and reductions which provide desferrioxamine B in 45% overall yield. Finally, a desamino analog of desferrioxamine is prepared in order to demonstrate the synthetic utility of the scheme as applied to desferrioxamine derivatives.

An Efficient Total Synthesis of Desferrioxamine B

The total syntheses of the microbial iron chelator desferrioxamine B hydrochloride and some analogues are described.The syntheric scheme is highly flexible, providing access to dihydroxamate, trihydroxamate, tetrahydroxamate, and higher homologues of desferrioxamines.The procedure also allows for access to primary amino nitrogen functionalized desferrioxamine.The scheme is predicated on the generation of the key intermediate O-benzyl-N-(4-cyanobutyl)hydroxylamine, which is acylated at the O-benzylhydroxylamine nitrogen with either succinic or acetic anhydride.The resu lting half acid amide or amide, respectively, is subjected to a series of high-yield condensations and reductions that provide desferrioxamine in 45percent overall yield.Finally a desamino analogue of desferrioxamine is prepared in order to demonstrate the synthetic utility of the scheme as applied to desferrioxamine derivatives.