39945-54-5

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL N-(3-BROMOPROPYL)CARBAMATE is used as a key intermediate in the synthesis of various pharmaceutical compounds for its ability to be incorporated into complex molecular structures.
Used in Anti-HIV Applications:
TERT-BUTYL N-(3-BROMOPROPYL)CARBAMATE is used as a building block in the synthesis of an active anti-HIV ethidium-arginine conjugate, which is specifically targeted against the viral TAR RNA sequence, playing a crucial role in the development of treatments for HIV.
Used in Synthesis of Biologically Active Compounds:
TERT-BUTYL N-(3-BROMOPROPYL)CARBAMATE is used as a versatile component in the creation of biologically active compounds, contributing to the advancement of medicine and healthcare by enabling the development of new therapeutic agents.

Synthesis

Benzyl N-(3-bromopropyl)carbamate synthesis: A solution of triphenylphosphine (9.4 g, 28.60 mmol) and carbon tetrabromide (7.5 g, 28.60 mmol) in dry THF was added dropwise (30 mL) to a solution of benzyl N-(3-hydroxypropyl)carbamate (3.0 g, 14.30 mmol) in the same solvent (30 mL). After 48 h of stirring at room temperature, the solution was filtrated to remove an insoluble solid. After evaporation of filtrate, the residue was dissolved in CH2Cl2 and the solution washed with H2O. The organic layer was dried over MgSO4. Removal of the solvent yielded an oily residue, which was purified by column chromatography (CH2Cl2 to MeOH). After evaporation of the solvents benzyl N-(3-bromopropyl)carbamate was obtained as an orange oil (3.2 g, 86.4 %). Rf (silica-gel, CHCl3) = 0.5. 1H-NMR (300 MHz, CDCl3, ppm) δH 7.32 (5H, m, Cbz), 5.15 (1H, br s, CBzNH-), 5.06 (2H, s, Cbz), 3.39 (2H, t), 3.30 (2H, q), 2.06 – 1.96 (2H, m). 13C-NMR (75.5 MHz, CDCl3, ppm) δc 156.4, 136.3, 128.4, 128.0, 127.9, 66.6, 39.2, 32.3, 30.6.

InChI:InChI=1/C11H14BrNO2/c1-9(12)7-13-11(14)15-8-10-5-3-2-4-6-10/h2-6,9H,7-8H2,1H3,(H,13,14)

Upstream product

• 18370-81-5 (3-bromopropyl)amine 
• 501-53-1 benzyl chloroformate 
• 5003-71-4 3-bromopropylamine hydrochloride 
• 174626-34-7 N-(benzyloxycarbonyl)-3-amino-1-propyl methanesulfonate 
• 1885-14-9 phenyl chloroformate 
• 34637-22-4 3-[(N-benzyloxycarbonyl)amino]propanol 
• 41236-20-8 3-bromopropan-1-amine hydrochloride 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 76799-54-7 3',5-dihydroxy-4'-methoxy-7-<propoxy>flavanone 
• 96839-28-0 N-benzyloxycarbonylamino<1-13C>butanenitrile 
• 79177-61-0 N-benzyloxycarbonylamino<1-amino-15N,1-13C>butanenitrile 
• 25313-19-3 N-(Carbobenzoxy)-3-(2-chlor-4-nitrophenoxy)-propylamin 
• 199612-53-8 {3-[(2R,6S)-4-(3-Carbazol-9-yl-propyl)-2,6-dimethyl-piperazin-1-yl]-propyl}-carbamic acid benzyl ester 
• 204061-09-6 7-(N-phenylmethoxycarbonyl)amino-4-azaheptanol 
• 218450-29-4 N-benzyloxycarbonyl-3-(4-hydroxy-4-phenylpiperidin-1-yl)propylamine 
• 437718-23-5 {4-[(3-benzyloxycarbonylamino-propyl)-(2-nitro-benzenesulfonyl)-amino]-butyl}-{2-[5-(2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-pentylcarbamoyl]-ethyl}-carbamic acid benzyl ester 
• 461441-09-8 N¹-benzyloxycarbonyl-N³-tert-butyloxycarbonyl-N²-2-naphthalenesulfonyl-spermidine 
• 882687-29-8 benzyl [3-(2,4-dibromo-6-formylphenoxy)propyl]carbamate 
• 882687-07-2 benzyl [3-(2,6-dibromo-4-formylphenoxy)propyl]carbamate 
• 870177-03-0 ethyl 4-(3-benzyloxycarbonylaminopropoxy)-3,5-dihydroxybenzoate 
• 882687-14-1 benzyl [3-(2-bromo-4-formylphenoxy)propyl]carbamate 
• 870177-64-3 ethyl 3-bromo-5-{3-{[(benzyloxy)carbonyl]amino}propyl}benzoate 

Relevant academic research and scientific papers

A Nexus between Theory and Experiment: Non-Empirical Quantum Mechanical Computational Methodology Applied to Cucurbit[n]uril?Guest Binding Interactions

A training set of eleven X-ray structures determined for biomimetic complexes between cucurbit[n]uril (CB[7 or 8]) hosts and adamantane-/diamantane ammonium/aminium guests were studied with DFT-D3 quantum mechanical computational methods to afford ΔG

NEW MACROCYCLIC LRRK2 KINASE INHIBITORS

Compounds of formula (I): wherein R, X1, X2, X3, Z1, Z2, Z3, A and Ra are as defined in the description. Medicaments.

Discovery of naphthalimide conjugates as fluorescent probes for α1-adrenoceptors

α1-Adrenoceptors (α1-ARs), including at least three subtypes, α1A, α1B and α1D, which play essential roles in G protein-coupled receptors (GPCRs), can convey multiple pivotal extracellular signals in varied tissues and organs. In this research, a series of napthalimide-based small-molecule fluorescent probes (1a–1f) for α1-ARs, including two parts, a pharmacophore (quinazoline and phenylpiperazine) for α1-AR recognition and a fluorophore (naphthalimide) for visualization, were designed and synthesized successfully. These compounds display excellent fluorescence property and high affinity to receptors, which were used successfully for in vitro visualization of α1-adrenoceptors.

Halogenation of primary alcohols using a tetraethylammonium halide/[Et 2NSF2]BF4 combination

The halogenation of primary alcohols is presented. The use of a combination of tetraethylammonium halide and [Et2NSF2]BF4 (XtalFluor-E) allows for chlorination and bromination reactions to proceed efficiently (up to 92% yield) with a wide range of alcohols. Iodination reactions are also possible albeit in lower yields.

GLUCOSE SENSOR MOLECULE

The present invention provides a glucose sensor having a glucose receptor containing a binding site of formula (I): wherein X, n, m and R1 are defined herein. Also provided is a glucose sensor molecule for use in such a glucose sensor, the glucose sensor molecule containing the binding site of formula (I). The binding site has been found to have particularly good selectivity for glucose.

The use of novel C-methylated spermidine derivatives to investigate the regulation of polyamine metabolism

The polyamines are organic polycations present at millimolar concentrations in eukaryotic cells where they participate in the regulation of vital cellular functions including proliferation and differentiation. Biological evaluation of rationally designed

Visible-light-mediated conversion of alcohols to halides

The development of new means of activating molecules and bonds for chemical reactions is a fundamental objective for chemists. In this regard, visible-light photoredox catalysis has emerged as a powerful technique for chemoselective activation of chemical bonds under mild reaction conditions. Here, we report a visible-light-mediated photocatalytic alcohol activation, which we use to convert alcohols to the corresponding bromides and iodides in good yields, with exceptional functional group tolerance. In this fundamentally useful reaction, the design and operation of the process is simple, the reaction is highly efficient, and the formation of stoichiometric waste products is minimized.

Syntheses of bifunctional 2,3-diamino propionic acid-based chelators as small and strong tripod ligands for the labelling of biomolecules with 99mTc

The labelling of targeting biomolecules requires small and hydrophilic complexes in order to not affect the binding properties of the vectors. 2,3-Diamino propionic acid (dap) is a small and strong, albeit scarcely used, tripod ligand for the fac-[99mTc(CO)3]+ moiety. We have introduced at the α-carbon atom in the basic dap structure various second functionalities such as carboxylato, amino and α-amino acid groups via various spacers in order to yield bifunctional chelators. These dap derivatives can be coupled to targeting molecules for application in molecular imaging. Full characterizations of the bifunctional chelators, X-ray structures of intermediates and of one rhenium complex, as well as labelling studies with 99mTc, are presented.

Synthesis of aminooxy and N-alkylaminooxy amines for use in bioconjugation

Five Boc-protected aminooxy and N-alkylaminooxy amines have been synthesized in 60-95% overall yield using a common synthetic strategy from readily available two- and three-carbon Cbz-protected amino alcohols. The amines can be linked to biomolecules via

ARYLPIPERAZINE-CONTAINING PYRROLE 3-CARBOXAMIDE DERIVATIVES FOR TREATING DEPRESSIVE DISORDERS

The present invention relates to novel arylpiperazine-containing pyrrole 3-carboxamide derivatives of formula (I) or a pharmaceutically acceptable salt thereof which is useful for preventing or treating depressive disorders. The present invention also provides a method for preparing the arylpiperazine-containing pyrrole 3-carboxamide derivatives or the pharmaceutically acceptable salt thereof, a pharmaceutical composition containing same, and a method for preventing or treating depressive disorders.