75178-87-9

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL N-(4-HYDROXYBUTYL)CARBAMATE is used as a building block for the synthesis of spermidine analogues, which are important compounds in the development of pharmaceuticals with potential applications in various therapeutic areas.
Used in Polymer Synthesis for In Vivo Delivery:
TERT-BUTYL N-(4-HYDROXYBUTYL)CARBAMATE is used as an intermediate for the synthesis of polymers that are utilized in the creation of in vivo delivery polyconjugate systems. These systems are designed to improve the delivery and efficacy of therapeutic agents, particularly in the field of drug delivery and biomedicine.
Used in Chemical Synthesis:
As a light yellow liquid, TERT-BUTYL N-(4-HYDROXYBUTYL)CARBAMATE can be employed in various chemical synthesis processes, contributing to the development of new compounds and materials with diverse applications across different industries.

InChI:InChI=1/C9H19NO3/c1-9(2,3)13-8(12)10-6-4-5-7-11/h11H,4-7H2,1-3H3,(H,10,12)

Upstream product

• 13325-10-5 4-Aminobutanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 57294-38-9 N-(tert-butoxycarbonyl)-4-aminobutanoic acid 
• 104700-36-9 ethyl (2E)-4-[(tert-butoxycarbonyl)amino]but-2-enoate 
• 67-56-1 methanol 
• 85909-08-6 tert-butyl 2-oxopyrrolidine-1-carboxylate 
• 67-63-0 isopropyl alcohol 
• 34619-03-9 tert-butyldicarbonate 
• 2508-29-4 5-hydroxypentylamine 

Downstream Products

• 84766-90-5 4-[N-(tert-butyloxycarbonyl)]amino-1-butanal 
• 164365-88-2 tert-butyl 4-bromobutylcarbamate 
• 180851-50-7 toluene-4-sulfonic acid 4-tert-butoxycarbonylaminobutyl ester 
• 189340-42-9 2-Chlorobenzenesulfonic acid 3-[[4-(N-tert-butoxycarbonyl)amino]butoxy]-5-methylphenyl ester 
• 446848-02-8 benzenesulfonic acid 4-tert-butoxycarbonylamino-butyl ester 
• 436864-52-7 2-(4-tert-butoxycarbonylaminobutoxy)-6-hydroxybenzoic acid methyl ester 
• 436864-68-5 methyl 3-bromo-6-{4-[(tert-butoxycarbonyl)amino]butoxy}-2-hydroxybenzoate 
• 313680-04-5 (3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-(4-{4-[(tert-butoxycarbonyl)amino]butoxy}benzyl)-2-hydroxypropylcarbamate 
• 262278-40-0 N-tert-butoxycarbonyl-4-amino-1-iodobutane 
• 740873-01-2 {4-[4-(3-nitrophenyl)piperazin-1-yl]butyl}carbamic acid tert-butyl ester 
• 894407-04-6 (5S,6S)-1-[4-(tert-butoxycarbonylamino)butyl]-5,6-dihydro-5-diphenylphosphoryloxy-6-[(2-naphthyl)methyl]pyridin-2-one 
• 894407-14-8 (5R,6S)-1-[4-(tert-butoxycarbonylamino)butyl]-5,6-dihydro-5-diphenylphosphoryloxy-6-[(2-naphthyl)methyl]pyridin-2-one 
• 894407-01-3 (3S,4S)-4-{N-[4-(tert-butoxycarbonylamino)butyl]-N-(2-nitrobenzenesulfonyl)}amino-3-[(tert-butyl)dimethylsiloxy]-5-(2-naphthyl)pent-1-ene 
• 849473-05-8 [4-(benzyl-methyl-amino)-butyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Biomimetic enterobactin analogue mediates iron-uptake and cargo transport intoE. coliandP. aeruginosa

The design, synthesis and biological evaluation of the artificial enterobactin analogueEntKLand several fluorophore-conjugates thereof are described.EntKLprovides an attachment point for cargos such as fluorophores or antimicrobial p

Hyperbranched Copolymers Based on Glycidol and Amino Glycidyl Ether: Highly Biocompatible Polyamines Sheathed in Polyglycerols

Functional hyperbranched polyglycerols (PGs) have recently garnered considerable interest due to their potential in biomedical applications. Here, we present a one-pot synthesis of hyperbranched PGs possessing amine functionality using a novel amino glycidyl ether monomer. A Boc-protected butanolamine glycidyl ether (BBAG) monomer was designed and polymerized with glycidol (G) through anionic ring-opening multibranching polymerization to yield a series of hyperbranched P(G-co-BBAG) with controlled molecular weights (4800-16700 g/mol) and relatively low molecular weight distributions (1.2-1.6). The copolymerization and subsequent deprotection chemistry allow the incorporation of an adjustable fraction of primary amine moieties (typically, 5-20% monomer ratio) within the hyperbranched PG backbones, thus providing potentials for varying charge densities and functionality in PGs. The copolymerization kinetics of G and BBAG was also evaluated using a quantitative in situ 13C NMR spectroscopic analysis, which revealed gradient copolymerization between the comonomers. The free amine groups within the deprotected P(G-co-BAG) copolymer were further utilized for a facile conjugation chemistry with a model molecule in a quantitative manner. Furthermore, the superior biocompatibility of the prepared P(G-co-BAG) polymers was demonstrated via cell viability assays, outperforming many existing polyamines possessing relatively high cytotoxicity. Taken together, the biocompatibility with facile conjugation chemistry of free amine groups sheathed within the framework of hyperbranched PGs holds the prospect of advancing biological and biomedical applications.

The synthesis of lysine α-ketoamide thrombin inhibitors via an epoxy amide ring opening

We describe a novel route for the preparation of substituted α-ketoamides of lysine. These compounds, due to the presence of an electrophilic carbonyl, display submicromolar activity toward the enzyme thrombin.

De-novo designed β-lysine derivatives can both augment and diminish the proliferation rates of E. coli through the action of Elongation Factor P

An investigation into the effect of modified β-lysines on the growth rates of eubacterial cells is reported. It is shown that the effects observed are due to the post translational modification of Elongation Factor P (EFP) with these compounds catalysed b

Novel Labelled Cannabinergic Ligands and Related Analogs

Novel cannabinoid ligands represented by the general formulas I, II, and III and methods for preparation and use within which one or more of a fluorescent ligand, nitroxide spin label, metal chelate, biotin moiety, or group with enhanced polarity may be incorporated. The compounds can bind to and modulate the cannabinoid CB1 and CB2 receptors and thereby considered specific ligands for these receptors. Some of the disclosed compounds that bind to cannabinoid CB1 and CB2 receptors can exhibit tight or irreversible binding characteristics for these receptors. Due to the presence of the imaging/diagnostic and/or therapeutic functional groups including fluorescent groups, nitroxide spin labels, metal chelates, biotin moieties, and groups with enhanced polarity, the disclosed compounds may be useful as imaging/diagnostic tools and/or therapeutic agents.

Application of bioorthogonal hetero-Diels-Alder cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid and vinyl thioether for imaging inside living cells

New bioorthogonal cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid as 1-oxa-1,3-butadienes and vinyl thioether as a dienophile has been applied to imaging inside living cells. The reaction is high yielding, selective, and fast in aqueous media. The proposed 1-oxa-1,3-butadiene derivative conjugated to a FITC fluorochrome selectively and rapidly labels the cancer cells pretreated with the dienophile-taxol. The second order rate constants k2 for various proposed bioorthogonal cycloadditions were estimated to be in the range from 0.9 × 10-2 M-1 s-1 to 1.4 M-1 s-1, which is much better than in the case of the first generation TQ-ligation (o-quinolinone quinone methide and vinyl thioether ligation, k2 = 1.5 × 10-3 M-1 s-1) and comparable or better to that for the second generation TQ-ligation (k2 = 2.8 × 10-2 M-1 s-1). The reaction rate constants k2 of proposed ligation reactions are in the range of the rate constants k2 for tetrazines and norbornenes or tetrazines and cyclopropenes. These findings indicate that this chemistry is suitable for in vitro imaging experiments.

TARGET PROTEIN EED DEGRADATION-INDUCING DEGRADUCER, PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING DISEASES RELATED TO EED, EZH2, OR PRC2, COMPRISING SAME AS ACTIVE INGREDIENT

The present invention relates to a target protein degradation-inducing Degraducer, a preparation method thereof, and a pharmaceutical composition for preventing or treating diseases related to EED, EZH2, or PRC2 comprising same as an active ingredient. A novel compound represented by formula 1, according to the present invention is a Degraducer compound that induces degradation of a target protein, i.e., embryonic ectoderm development (EED) or polycomb repressive complex 2 (PRC2), utilizing cereblon E3 ubiquitin ligase, von Hippel-Lindau tumor suppressor (VHL) E3 ubiquitin ligase, mouse double minute 2 homolog (MDM2) E3 ubiquitin ligase, and cellular inhibitor of apoptosis protein 1 (cIAP) E3 ubiquitin ligase, wherein the compound has an aspect of remarkably achieving target protein degradation-inducing activity through a ubiquitin proteasome system (UPS), and therefore there is a useful effect in that it is possible to provide a pharmaceutical composition for preventing or treating diseases or conditions related to a target protein, and a functional health food composition for preventing or improving same, comprising said compound as an active ingredient.

Synthesis and Pharmacological Evaluation of σ2 Receptor Ligands Based on a 3-Alkoxyisoxazole Scaffold: Potential Antitumor Effects against Osteosarcoma

Since its initial discovery as the basis for nicotinic acetylcholine receptor ligands, the 3-alkoxyisoxazole scaffold has been shown to be a versatile platform for the development of potent σ1 and σ2 receptor ligands. Herein we report a further SAR exploration of the 3-alkoxyisoxazole scaffold with the aim of obtaining potent σ2 receptor ligands. Various substitutions on the benzene ring and at the basic amino regions resulted in a total of 21 compounds that were tested for their binding affinities for the σ2 receptor. In particular, compound 51 [(2S)-1-(4-ammoniobutyl)-2-(((5-((3,4-dichlorophenoxy)methyl)isoxazol-3-yl)oxy)methyl)pyrrolidin-1-ium chloride] was identified as one of the most potent σ2 ligands within the series, with a Ki value of 7.9 nM. It demonstrated potent antiproliferative effects on both osteosarcoma cell lines 143B and MOS?J (IC50 values of 0.89 and 0.71 μM, respectively), relative to siramesine (IC50 values of 1.81 and 2.01 μM). Moreover, compound 51 inhibited clonal formation of osteosarcoma 143B cells at 1 μM, corresponding to half the dose required of siramesine for similar effects. The general cytotoxicity profile of compound 51 was assessed in a number of normal cell lines, including HaCaT, HAF, and LO2 cells. Furthermore, FACS analysis showed that compound 51 likely inhibits osteosarcoma cell growth by disruption of the cell cycle and promotion of apoptosis.

Preparation method of 4-(BOC-amino)-1-butanol

The invention discloses a preparation method of 4-(BOC-amino)-1-butanol. The method comprises the following steps: reacting a proper amount of 2, 3-dihydrofuran with an acidic solution to obtain 2, 3-dihydro-5-methyl furan; mixing the obtained 2, 3-dihydro-5-methyl furan with hydrochloride, and then adding the mixture into an alkaline solution for reaction to obtain isobutyl nitrite; reacting isobutyl nitrite under the action of a reducing agent to generate 4-amino-1-butyl alcohol; and reacting 4-amino-1-butyl alcohol with di-tert-butyl dicarbonate in tetrahydrofuran to generate 4-(BOC-amino)-1-butyl alcohol; according to the preparation method of the 4-(BOC-amino)-1-butanol, the total yield of the product is as high as 70%, the reaction temperature is low, and the safety coefficient is high), the reducing agent is cheaper than that in the prior art, the experimental operation method is simple, the steps are short, and the method is suitable for large-scale production.

COMPOUNDS AND USES THEREOF

The present disclosure features compounds and methods useful for the treatment of BAF complex-related disorders.