129392-85-4

Usage

Uses

Used in Pharmaceutical Synthesis:
Tert-butyl (4-azidobutyl)carbamate is used as a reagent for the synthesis of pharmaceuticals and other biologically active compounds. Its unique structure allows for the introduction of nitrogen functionality, which is essential in the development of new drugs with specific therapeutic properties.
Used in Organic and Polymer Chemistry:
In the field of organic and polymer chemistry, tert-butyl (4-azidobutyl)carbamate is utilized in the preparation of materials. Its steric hindrance and stability contribute to the formation of desired molecular structures, enhancing the properties of the resulting compounds.
Used in the Creation of Complex Organic Molecules:
Tert-butyl (4-azidobutyl)carbamate serves as a building block in the synthesis of complex organic molecules. Its ability to introduce nitrogen functionality and provide stability makes it a valuable component in the construction of intricate molecular structures with potential applications in various industries.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 88192-20-5 4-azidobutan-1-amine 
• 164365-88-2 tert-butyl 4-bromobutylcarbamate 
• 180851-50-7 toluene-4-sulfonic acid 4-tert-butoxycarbonylaminobutyl ester 
• 33545-98-1 N-(4-aminobutyl)carbaminsaeure-(tert-butyl)ester-hydrochlorid 
• 68076-36-8 1-amino-4-[(tert-butyloxycarbonyl)amino]butane 
• 75178-87-9 (4-hydroxybutyl)carbamic acid tert-butyl ester 
• 174626-25-6 methanesulfonic acid 4-tert-butoxycarbonylaminobutyl ester 

Downstream Products

• 1654738-58-5 C₂₈H₄₂N₈O₄ 
• 1446011-79-5 di-tert-butyl ((4,4'-(((4-sulfamoylphenethyl)azanediyl)bis(methylene))bis(1H-1,2,3-triazole-4,1-diyl))bis(butane-4,1-diyl))dicarbamate 
• 345898-28-4 4,8-bis(benzyloxycarbonyl)-N¹-(2,2,2-trichloroethoxycarbonyl)-N¹²-(tert-butoxycarbonyl)-4,8-diaza-1,12-dodecanediamine 
• 68076-36-8 1-amino-4-[(tert-butyloxycarbonyl)amino]butane 
• 33545-98-1 N-(4-aminobutyl)carbaminsaeure-(tert-butyl)ester-hydrochlorid 
• 1267640-80-1 4-azidobutan-1-amine hydrochloride 
• 88192-20-5 4-azidobutan-1-amine 

Relevant academic research and scientific papers

An efficient and practical method for the synthesis of mono-N-protected α,ω-diaminoalkanes

The large-scale synthesis of mono-N-protected (Cbz, Boc, Ts, and Ns) α,ω-diaminoalkanes (the number of carbon atoms=3, 4, 5 and 6) are accomplished in 81-94% yield by the protection of amine and subsequent reduction of an azido group from α,ω-azido alkyl amines. α,ω-Azido alkyl amines are prepared efficiently by the partial reduction of α,ω-diazidoalkanes which are obtained from the corresponding dibromoalkanes.

Azido-Desferrioxamine Siderophores as Functional Click-Chemistry Probes Generated in Culture upon Adding a Diazo-Transfer Reagent

This work aimed to undertake the in situ conversion of the terminal amine groups of bacterial desferrioxamine (DFO) siderophores, including desferrioxamine B (DFOB), to azide groups to enable downstream click chemistry. Initial studies trialed a precursor-directed biosynthesis (PDB) approach. Supplementing Streptomyces pilosus culture with blunt-end azido/amine non-native substrates designed to replace 1,5-diaminopentane as the native diamine substrate in the terminal amine position of DFOB did not produce azido-DFOB. Addition of the diazo-transfer reagent imidazole-1-sulfonyl azide hydrogen sulfate to spent S. pilosus medium that had been cultured in the presence of 1,4-diaminobutane, as a viable native substrate to expand the suite of native DFO-type siderophores, successfully generated the cognate suite of azido-DFO analogues. CuI-mediated or strain-promoted CuI-free click chemistry reactions between this minimally processed mixture and the appropriate alkyne-bearing biotin reagents produced the cognate suite of 1,4-disubstituted triazole-linked DFO-biotin compounds as potential molecular probes, detected as FeIII-loaded species. The amine-to-azide transformation of amine-bearing natural products in complex mixtures by the direct addition of a diazo-transfer reagent to deliver functional click chemistry reagents adds to the toolbox for chemical proteomics, chemical biology, and drug discovery.

Structure-based design and synthesis of triazole-based macrocyclic inhibitors of norovirus protease: Structural, biochemical, spectroscopic, and antiviral studies

Outbreaks of acute gastroenteritis caused by noroviruses constitute a public health concern worldwide. To date, there are no approved drugs or vaccines for the management and prophylaxis of norovirus infections. A potentially effective strategy for the development of norovirus therapeutics entails the discovery of inhibitors of norovirus 3CL protease, an enzyme essential for noroviral replication. We describe herein the structure-based design of the first class of permeable, triazole-based macrocyclic inhibitors of norovirus 3C-like protease, as well as pertinent X-ray crystallographic, biochemical, spectroscopic, and antiviral studies.

Comparative Studies of Three Pairs of α- And γ-Conjugated Folic Acid Derivatives Labeled with Fluorine-18

The folate receptor (FR) is upregulated in various epithelial cancer types (FR α-isoform), while healthy tissues show only restricted expression. FR-targeted imaging using folate radiopharmaceuticals is therefore a promising approach for the detection of FR-positive cancer tissue. Almost all folate-based radiopharmaceuticals have been prepared by conjugation at the γ-carboxylic functionality of the glutamate moiety of folic acid. In this work, three pairs of fluorinated α- and γ-conjugated folate derivatives were synthesized and their in vitro and in vivo properties compared. The syntheses of all six regioisomers were obtained in good chemical yields using a multistep synthetic approach including the highly selective Cu(I)-catalyzed 1,3-dipolar cycloaddition. The radiosyntheses of the α- and γ-conjugated 18F-labeled folate derivatives were accomplished in moderate to good radiochemical yields, high radiochemical purities (>95%), and specific activities ranging from 25 to 196 GBq/μmol. In vitro, all folate derivatives showed high binding affinity to the FR-α (IC50 = 1.4-2.2 nM). In vivo PET imaging and biodistribution studies in FR-positive KB tumor-bearing mice demonstrated similar FR-specific tumor uptake for both regioisomers of each pair of compounds. However, FR-unspecific liver uptake was significantly lower for the α-regioisomers compared to the corresponding γ-regioisomers. In contrast, kidney uptake was up to 50% lower for the γ-regioisomers than for the α-regioisomers. These results show that the site of conjugation in the glutamyl moiety of folic acid has a significant impact on the in vivo behavior of 18F-based radiofolates, but not on their in vitro FR-binding affinity. These findings may potentially stimulate new directions for the design of novel 18F-labeled folate-based radiotracers.

Synthesis, biological activity and structural study of new benzotriazole-based protein kinase CK2 inhibitors

A new series of 4,5,6,7-tetrabromobenzotriazole (TBB) derivatives was synthesized and characterized as CK2 inhibitors. They were readily synthesized using a click chemistry approach based on a Cu(i)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC). Some of the synthesized compounds present interesting inhibitory activities using an in vitro assay, with Ki values in the low micro molar range and a high degree of selectivity against a panel of 24 kinases. Selected compounds were tested for their antiproliferative effect on several cancer cell lines, and for their proapoptotic activity towards human Jurkat T-leukemia and MCF-7 breast adenocarcinoma cells, showing that they can be proposed as promising anticancer agents. Docking studies as well as crystallographic analysis allowed us to identify ligand-CK2 interactions that account for the molecular recognition process, and can help to further optimize this family of compounds as CK2 inhibitors.

18 F-LABELLED FOLATES

The present invention is directed towards new 18F-folate radiopharmaceuticals, wherein fluorine-18 is covalently linked through a triazole- or tetrazole linker to a folate or derivative thereof, a method of their preparation, as well as their use in diagnosis and monitoring of therapy of cancer and inflammatory and autoimmune diseases.

NOVEL AZALIDE AND AZALACTAM DERIVATIVES AND PROCESS FOR THE PRODUCTION OF THE SAME

A compound represented by the following general formula (1) or a pharmaceutically acceptable salt thereof, which is useful for a prophylactic and/or therapeutic treatment of a microbial infectious disease. [R1 is hydrogen atom, or a linear C1-6 alkylcarbonyl group; R2 is hydrogen atom, or a C1-6 alkylcarbonyl group; R3 is hydrogen atom, a C1-6 alkyl group, a C1-6 alkylcarbonyl group, a C1-6 alkenyl group, a C2-6 alkenylcarbonyl group, a C2-6 alkynyl group, or an Ar-B- group (Ar represents an aryl group, or a heterocyclic group, and B is a C1-6 alkyl group, a C1-6 alkylcarbonyl group, a C2-6 alkenyl group, a C2-6 alkenylcarbonyl group, or a C2-6 alkynyl group); R5, R6, R7, and R8 represent hydrogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, or an Ar-B'- group (B' is a C1-6 alkyl group, a C2-6 alkenyl group, or a C2-6 alkynyl group); X is oxygen atom, or an -NR4- group (R4 is hydrogen atom, a C1-6 alkyl group, or a C1-6 alkyl group which may be substituted with an Ar group); and R4' is hydrogen atom, or a group represented by the aforementioned formula (a) (R3" and R4" represent hydrogen atom, or a linear or branched C1-6 alkylcarbonyl group)]

Mono-Protected Diamines. Nα-tert-Butoxycarbonyl α,ω-Alkanediamine Hydrochlorides from Amino alcohols.

Nα-tert-Butoxycarbonyl α,ω-alkanediamine hydrochlorides 3a-e are prepared from the amino alcohols in yields of 66-87percent.Reaction of the free amine with di-tert-butyl dicarbonate gives the N-tert-Butoxycarbonylamino alcohol 1a-e.One-pot conversion to the azide 2a-e via the mesylate under phase-transfer conditions followed by hydrogenolysis in the presence of chloroform yields the title compounds.