129245-21-2

Usage

Uses

N-?(5-?Aminopentyl)?-?N-?(phenylmethoxy)?-?carbamic Acid 1,?1-?Dimethylethyl Ester is an intermediate in synthesizing Deferoxamine-d7 TFA Salt (D228982), a labelled Deferoxamine Mesylate (D228980), which is an iron chelating agent used in therapy for patients with sickle cell diseases and iron overload. Studies suggest that it can exert potential antioxidant neuroprotective effects in stroke patients.

InChI:InChI=1/C17H28N2O3/c1-17(2,3)22-16(20)19(13-9-5-8-12-18)21-14-15-10-6-4-7-11-15/h4,6-7,10-11H,5,8-9,12-14,18H2,1-3H3

Upstream product

• 128173-50-2 O-Benzyl-N-(tert-butoxycarbonyl)-N-(4-cyanobutyl)-hydroxylamine 
• 6280-87-1 δ-chlorovaleronitrile 
• 79722-21-7 tert-butyl N-(benzyloxy)carbamate 
• 954-81-4 N-(5-bromopentyl)phthalimide 
• 111-24-0 1,5-dibromo-pentane 

Downstream Products

• 130946-40-6 27--6,17-bis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22-tetraazaheptacosanenitrile 
• 129245-22-3 N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid 
• 135638-85-6 22-(tert-butoxycarbonyl)-11,22-bis(benzyloxy)-12,15-dioxo-11,16,22-triaza-2,5,8-trioxadocosane 
• 135638-88-9 33-(tert-butoxycarbonyl)-11,22,33-tris(benzyloxy)-12,15,23,26-tetraoxo-11,16,22,27,33-pentaaza-2,5,8-trioxatritriacontane 
• 160388-21-6 N-(Benzyloxy)-1,5-pentanediamine 
• 284666-53-1 17-(tert-butoxycarbonyl)-1,6,17-tris(benzyloxy)-7,10-dioxo-6,11,17-triazaheptadecane 
• 284666-57-5 28-(tert-butoxycarbonyl)-1,6,17,29-tetrakis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22,28-pentaazaoctacosane 
• 284666-62-2 1,6,17-tris(benzyloxy)-7,10-dioxo-6,11,17-triazaheptadecane 
• 284666-55-3 5,16,21-tris(benzyloxy)-4,12,15-trioxo-5,11,16-triazahenicosanoic acid 
• 284666-64-4 1,6,17,29-tetrakis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22,28-pentaazaoctacosane 
• 284666-59-7 tetra-O-benzyl danoxamine 
• 70-51-9 deferoxamine 
• 130946-41-7 27--6,17-bis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22-tetraazaheptacosanenitrile 
• 112139-65-8 N'-<5-<<4-<<5-pentyl>amino>-1,4-dioxobutyl>(phenylmethoxy)amino>pentyl>-N-(4-cyanobutyl)-N-(phenylmethoxy)butanediamide 

Relevant academic research and scientific papers

Design, Synthesis and Evaluation of AdSS Bisubstrate Inhibitors

Many cancers lack the expression of methylthioadenosine phosphorylase (MTAP). These cancers require adenylosuccinate synthetase (AdSS) for nucleic acid synthesis. By inhibiting adenylosuccinate synthetase, we potentially have a new therapeutic agent. Bisubstrate inhibitors were synthesized and evaluated against purified AdSS. The best activity was obtained with adenosine bearing a four-carbon linker that connects the N-formyl-N-hydroxy moiety to the 6-position of the purine nucleoside.

MULTIDENTATE BIFUNCTIONAL CHELATING AGENTS FOR RADIONUCLIDE COMPLEXATION IN DIAGNOSTICS AND THERAPY

The invention relates to octadentate ligands of a general formula R1 - D - X - D - X - D - X - D - E - R2, wherein D is C(O)N(OH) or N(OH)C(O), pyrimidinone or pyridinone, each X independently of any other X is a saturated or partial

Forward and reverse (Retro) Iron(III) or gallium(III) desferrioxamine e and ring-expanded analogues prepared using metal-templated synthesis from endo -hydroxamic acid monomers

A metal-templated synthesis (MTS) approach was used to preorganize the forward endo-hydroxamic acid monomer 4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanoic acid (for-PBH) about iron(III) in a 1:3 metal/ligand ratio to furnish the iron(III) siderophore for-[Fe(DFOE)] (ferrioxamine E) following peptide coupling. Substitution of for-PBH with the reverse (retro) hydroxamic acid analogue 3-(6-amino-N-hydroxyhexanamido)propanoic acid (ret-PBH) furnished ret-[Fe(DFOE)] (ret-ferrioxamine E). As isomers, for-[Fe(DFOE)] and ret-[Fe(DFOE)] gave identical mass spectrometry signals ([M + H+]+, m/zcalc 654.3, m/zobs 654.3), yet for-[Fe(DFOE)] eluted in a more polar window (tR = 23.44 min) than ret-[Fe(DFOE)] (tR = 28.13 min) on a C18 reverse-phase high-performance liquid chromatography (RP-HPLC) column. for-[Ga(DFOE)] (tR = 22.99 min) and ret-[Ga(DFOE)] (tR = 28.11 min) were prepared using gallium(III) as the metal-ion template and showed the same trend for the retention time. Ring-expanded analogues of for-[Fe(DFOE)] and ret-[Fe(DFOE)] were prepared from endo-hydroxamic acid monomers with one additional methylene unit in the amine-containing region, 4-[(6-aminohexyl)(hydroxy)amino]-4-oxobutanoic acid (for-HBH) or 3-(7-amino-N-hydroxyheptanamido)propanoic acid (ret-HBH), to give the corresponding tris(homoferrioxamine E) macrocycles, for-[Fe(HHDFOE)] or ret-[Fe(HHDFOE)] ([M + H+]+, m/zcalc 696.3, m/zobs 696.4). The MTS reaction using a constitutional isomer of for-HBH that transposed the methylene unit to the carboxylic acid containing region, 5-[(5-aminopentyl)(hydroxy)amino]-5-oxopentanoic acid (for-PPH), gave the macrocycle for-[Fe(HPDFOE)] in a yield significantly less than that for for-[Fe(HHDFOE)], with the gallium(III) analogue for-[Ga(HPDFOE)] unable to be detected. The work demonstrates the utility and limits of MTS for the assembly of macrocyclic siderophores from endo-hydroxamic acid monomers. Indirect measures (RP-HPLC order of elution, c log P values, molecular mechanics, and density functional theory calculations) of the relative water solubility of the ligands, the iron(III) macrocycles, and the apomacrocycles were consistent in identifying for-DFOE as the most water-soluble macrocycle from for-DFOE, ret-DFOE, for-HHDFOE, ret-HHDFOE, and for-HPDFOE. From this group, only for-DFOE is known in nature, which could suggest that water solubility is an important trait in its natural selection.

Total synthesis of the siderophore Danoxamine

The total synthesis of the linear trihydroxamate siderophore, Danoxamine, is described. Danoxamine is a siderophore component of the naturally occurring siderophore-drug conjugates Salmycin A-D. The synthesis of Danoxamine features a series of coupling re

THE TOTAL SYNTHESIS OF BISUCABERIN

The first total synthesis of 6,17-dihydroxy-1,6,12,17-tetraazacyclodocosane-2,5,13,16-tetrone (bisucaberin) is presented.The synthetic scheme employed in this study illustrates the utility of O-benzyl-N-(tert-butoxycarbonyl)-N-(4-cyanobutyl)hydroxylamine