83948-53-2

Usage

Uses

Used in Pharmaceutical Synthesis:
tert-Butyl 3-bromopropylcarbamate is used as an alkylating reagent for the synthesis of Benzydamine analogs, which are activators for soluble guanylate cyclase. This application is significant in the development of drugs targeting specific biological pathways.
Used in Cancer Research:
In the field of cancer research, tert-Butyl 3-bromopropylcarbamate is utilized for the synthesis of N-substituted chromenotriazolopyrimidine, a human murine double minute 2 (MDM2) inhibitor. MDM2 inhibitors have the potential to play a crucial role in cancer treatment by targeting proteins that regulate the cell cycle and apoptosis.
Used in Organic Chemistry:
tert-Butyl 3-bromopropylcarbamate is also used for the synthesis of protected amines from piperidine derivatives, which are essential building blocks for the creation of sulfonamide series. Sulfonamides are a class of antibiotics that have been widely used in the treatment of bacterial infections.
Used in Polymer Science:
Furthermore, tert-Butyl 3-bromopropylcarbamate can be employed for the post-polymerization quaternization of polymers. This process allows the synthesis of functional cationic polymers, which have applications in various fields, including the development of antimicrobial agents to combat resistant bacterial strains.

InChI:InChI=1/C8H16BrNO2/c1-8(2,3)12-7(11)10-6-4-5-9/h4-6H2,1-3H3,(H,10,11)

Upstream product

• 558-13-4 carbon tetrabromide 
• 58885-58-8 N-tert-butoxycarbonyl-3-aminopropanol 
• 216959-40-9 [(3-bromo-propyl)-tert-butoxycarbonyl-amino]-oxo-acetic acid ethyl ester 

Downstream Products

• 83948-50-9 1-<(tert-Butoxycarbonyl)amino>-3-propane 
• 83948-55-4 N-Benzyloxy-acetimidic acid 3-tert-butoxycarbonylamino-propyl ester 
• 122632-09-1 C₄₇H₆₈N₈O₉ 
• 83948-65-6 C₂₀H₃₂N₂O₅ 
• 216502-92-0 (S)-3-[4-(3-tert-Butoxycarbonylamino-propoxy)-3-nitro-phenyl]-2-(2,2,2-trifluoro-acetylamino)-propionic acid tert-butyl ester 
• 251369-17-2 1-(3-(4-(1-N-BOC-3-aminopropyl)piperidyl)propyl)-2-(4-chlorophenoxymethyl)-4-methylbenzimidazole 
• 186347-50-2 N-(3-tert-butoxycarbonylaminopropyl)-4-cyano-4-phenylpiperidine 
• 239807-64-8 3-[4-[2-(1-methylethoxy)phenyl]-1-piperazinyl]propylcarbamic acid, 1,1-dimethylethyl ester 
• 186347-39-7 4-cyano-4-(2-methylphenyl)-N-[3-{(1,1-dimethyl-ethoxy) carbonyl}amino]propyl piperidine 
• 256951-74-3 2-[1-(3-tert-butoxycarbonylaminopropyl)-piperidin-4-yl] benzonitrile 
• 256951-81-2 1-(3-tert-Butoxycarbonylamino-propyl)-4-(4-fluorophenyl)-4-cyano-piperidine 
• 256951-78-7 {3-[4-(2-cyano-4-fluoro-phenyl)-piperidin-1-yl]-propyl}-carbamic acid tert-butyl ester 
• 268205-04-5 4-(2-Cyanophenyl)-4-cyano-N-(3-[N-{1,1-dimethyl ethoxycarbonyl}]amino)propylpiperidine 
• 216311-14-7 1-(3-tert-Butoxycarbonylamino-propyl)-4-(2,4-difluorophenyl)-piperidine-4-carbonitrile 

Relevant academic research and scientific papers

PHTHALOCYANINE DYE COMPOUNDS, CONJUGATES AND METHODS OF USE THEREOF

Disclosed herein are phthalocyanine dyes, and conjugates thereof, useful as fluorescent reporters for bioassays, for optical imaging and as therapeutic conjugates as the photosensitizing agents in light-based therapies including photoimmuno therapy (PIT). Certain phthalocyanine dyes disclosed herein are water soluble, and possess photophysical and photochemical profiles useful for use in imaging or therapy.

Graphene Oxide Cellular Delivery of Hydrophilic Small Molecules

Unmodified graphene oxide conjugated with hydrophilic small molecules for cellular delivery.

Effect of spermine-derived AGEs on oxidative stress and polyamine metabolism

Non-enzymatic glycation between proteins and carbohydrates, such as advanced glycation end products (AGEs), are naturally occurring compounds implicated in aging and numerous degenerative diseases. Methyl glyoxal (MG), which is an intermediate of the AGE biosynthetic pathway, is known to react with primary amines of proteins to create a wide range of AGE modifications, such as carboxyethyl lysine (CEL) and methylglyoxal-derived lysine dimer (MOLD). As a means to investigate and probe the ROS production pathways of AGEs, low molecular weight compounds carboxyethyl spermine (CES) and methylglyoxal-derived spermine dimer (MOSD) were synthesized, which replace lysine with another highly nucleophilic biological amine, spermine (SPM). Contrary to expectations, results show CES- and MOSD-induced oxidative stress proceeds through different pathways. As such, we have developed useful probes that can be used to better understand and investigate pathways related to acrolein-based oxidative stress and/or polyamine metabolic pathways.

Light-mediated deoxygenation of alcohols with a dimeric gold catalyst

A new protocol for the reductive deoxygenation of primary alcohols was explored. This photo-mediated method combines a novel approach to bromination of alcohols merged with the powerful reducing capability of [Au2(dppm)2]Cl2 [dppm = 1,1-bis(diphenylphosphino)methane] as a photoredox catalyst. The highly efficient methods discussed are marked by the use of UVA light-emitting diodes, which have significantly reduced reaction times and lowered setup cost.

COMPOUNDS FOR THE REDUCTION OF BETA-AMYLOID PRODUCTION

Compounds of the formula (I) are provided, including pharmaceutically acceptable salts thereof: which modulate β-amyloid peptide (β-AP) production, and are useful in the treatment of Alzheimer's Disease and other conditions affected by -amyloid peptide (β-AP) production.

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.

Module assembly for protein-surface recognition: Geranylgeranyltransferase I bivalent inhibitors for simultaneous targeting of interior and exterior protein surfaces

Synthetic chemical probes designed to simultaneously targeting multiple sites of protein surfaces are of interest owing to their potential application as site specific modulators of protein-protein interactions. A new approach toward bivalent inhibitors of mammalian type I geranylgeranyltransferase (GGTase I) based on module assembly for simultaneous recognition of both interior and exterior protein surfaces is reported. The inhibitors synthesized in this study consist of two modules linked by an alkyl spacer; one is the tetrapeptide CVIL module for binding to the interior protein surface (active pocket) and the other is a 3,4,5-alkoxy substituted benzoyl motif that contains three aminoalkyl groups designed to bind to the negatively charged protein exterior surface near the active site. The compounds were screened by two distinct enzyme inhibition assays based on fluorescence spectroscopy and incorporation of a [ 3H]-labeled prenyl group onto a protein substrate. The bivalent inhibitors block GGTase I enzymatic activity with Ki values in the submicromolar range and are approximately one order of magnitude and more than 150 times more effective than the tetrapeptide CVIL and the methyl benzoate derivatives, respectively. The bivalent compounds 6 and 8 were shown to be competitive inhibitors, suggesting that the CVIL module anchors the whole molecule to the GGTase I active site and delivers the other module to the targeting protein surface. Thus, our module-assembly approach resulted in simultaneous multiple-site recognition, and as a consequence, synergetic inhibition of GGTase I activity, thereby providing a new approach in designing protein-surface-directed inhibitors for targeting protein-protein interactions.

N-Boc ethyl oxamate: A new nitrogen nucleophile for use in Mitsunobu reactions

N-Boc ethyl oxamate can be directly coupled with primary and secondary alcohols under Mitsunobu conditions to afford various N-Boc mines after mild deprotection.

Molecular diversity of novel amino acid based dendrimers

We have expanded the recently introduced methodology for the preparation of a novel amino acid based dendrimer in order to be able to synthesize a diversity of dendrimers. For this purpose different hydroxybenzoic acids and amino alcohols were used to prepare the required monomers, necessary for construction of the respective dendrimers.