51857-17-1

Basic information

• Product Name: N-tert-Butoxycarbonyl-1,6-hexanediamine
• Synonyms: 1-BOC-AMINO-1,6-HEXANEDIAMINE;1-BOC-1,6-DIAMINOHEXANE;AURORA KA-4392;AURORA KA-7545;AURORA KA-7567;TIMTEC-BB SBB006530;TERT-BUTYL N-(6-AMINOHEXYL)CARBAMATE;N-(6-AMINOHEXYL)CARBAMIC ACID TERT-BUTYL ESTER
• CAS NO: 51857-17-1
• Molecular Formula: C₁₁H₂₄N₂O₂
• Molecular Weight: 216.32
• EINECS: -0
• Product Categories: All Aliphatics;Monoprotected Diaminoalkanes;N-Boc-diaminoalkanes;Aliphatics;Amines
• Mol File: 51857-17-1.mol
• Article Data: 108

Chemical Properties

• Boiling Point: 106-110 °C (0.3 mmHg)
• Flash Point: 125 °C
• Appearance: Clear light yellow/Viscous Liquid
• Density: 0.965 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.000233mmHg at 25°C
• Refractive Index: n20/D 1.462
• Storage Temp.: 0-10°C
• Solubility: Soluble in dichloromethane and ethyl acetate.
• PKA: 12.93±0.46(Predicted)
• Sensitive: Air Sensitive
• BRN: 2089264
• CAS DataBase Reference: N-tert-Butoxycarbonyl-1,6-hexanediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-tert-Butoxycarbonyl-1,6-hexanediamine(51857-17-1)
• EPA Substance Registry System: N-tert-Butoxycarbonyl-1,6-hexanediamine(51857-17-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• F: 10-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 51857-17-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

N-Boc-1,6-diaminohexane is used to prepare 1,3-Bis[6-(Boc-amino)hexyl]urea by reacting with carbonyl dichloride in the presence of triethylamine. Further, it is used as a reagent for the introduction of a C6-spacer.

Application

N-Boc-1,6-hexanediamine can be used as a linear hexyl spacer (C6-spacer) to synthesize:Biodegradable poly(disulfide amine)s for gene delivery.A multifunctional dendrimer for theranostics.Polyamide platinum anti-cancer complexes designed to target cancer specific DNA sequences.Self-assembled monolayers (SAMs) that resist adsorption of proteins.[N-(6-(4-Hydroxy-6-isopropylamino-1,3,5-triazin-2-ylamino)hexyl)-5-hydroxy-1,4-naphthoquinone-3-propionamide] (JUG-HATZ), which can be used in designing electrochemical immunosensors.

Preparation

synthesis of N-BOC-1,6-diaminohexane: 1,6-Diaminohexane 3 (Fig. 1) (100 g, 0.86 mol) was dissolved in CH2Cl2 (300 ml) and cooled in an ice bath to 0–3°C. To the stirred solution 0.3 eq. di-tert-butyl bicarbonate (62.6 g, 0.29 mol) was added slowly over a period of 1 h. The reaction was allowed to warm up to r.t., and proceeded overnight. The reaction mixture was extracted with saturated aqueous NaHCO3 (50 ml, three times). The organic phases were pooled, dried, and evaporated under reduced pressure. The resulting oil was dissolved in 200 ml, 1 N HCl and extracted with ether. The aqueous phase was washed with ether, made basic to a pH of 10 with aqueous 2 N NaO3, and extracted with ethyl acetate. The organic phases were pooled, dried, and evaporated under reduced pressure. The resulting oil was dissolved in 200 ml, 1 N HCL and extracted with ether. The aqueous phase was washed with ether, made basic to a pH of 10 with aqueous 2 N NaOH, and extracted with ethyl acetate. The organic extracts were pooled, dried over Na2SO4 and evaporated to give 10.5 g of homogeneous N-BOC-1, 6- diaminohexane 2c (Fig. 1) as a yellow oil which was used without further purification. TLC Rf 0.51; 1H NMR (CDCL3) d 4.54 (bs, 1H; NH), 3.05 1 2.62 (m, 4H; NCH2), 1.41 (m, 9H; CH3), 1.29 (m, 8H; CH2). Evaluation of aminoalkylmethacrylate nanoparticles as colloidal drug carrier systems. Part I: synthesis of monomers, dependence of the physical properties on the polymerization methods

InChI:InChI=1/C11H24N2O2/c1-11(2,3)15-10(14)13-9-7-5-4-6-8-12/h4-9,12H2,1-3H3,(H,13,14)/p+1

Upstream product

• 124-09-4 1,6-Hexanediamine 
• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 16644-54-5 N,N'-bis(tert-butoxycarbonyl)-1,6-hexanediamine 
• 118110-05-7 tert-butyl (5-cyanopentyl)carbamate 
• 60-32-2 6-aminohexanoic acid 
• 34619-03-9 tert-butyldicarbonate 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 129392-87-6 1-Azido-6-(tert-butoxycarbonylamino)hexane 
• 85535-56-4 ε-<(tert-Butoxycarbonyl)amino>capronamide 
• 6404-29-1 6-(tert-butoxycarbonylamino)hexanoic acid 
• 56934-05-5 N-(6-aminohexyl)-2,2,2-trifluoroacetamide 
• 251557-12-7 N-{6-{[(tert-butoxy)carbonyl]amino}hexyl}-2,2,2-trifluoroacetamide 

Downstream Products

• 268544-19-0 N-6-(t-butoxycarbonylamino)hexyl 3-(2-hydroxyphenyl)propionamide 
• 251557-14-9 4-N-{6-{[(tert-butoxy)carbonyl]amino}hexyl}-2',3'-dideoxy-5'-O-(dimethoxytrityl)cytidine 
• 718605-04-0 (6-{4-[(2-Amino-4-oxo-1,4-dihydro-pteridin-6-ylmethyl)-(2,2,2-trifluoro-acetyl)-amino]-benzoylamino}-hexyl)-carbamic acid tert-butyl ester 
• 65953-56-2 N-(6-aminohexyl)-5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d] imidazol-4-yl)pentanamide 
• 1374209-88-7 N-(6-(5,11-dioxo-5H-indeno[1,2-c]isoquinolin-6(11H)-yl)hexyl)-4-methylbenzenesulfonamide 
• 1374209-99-0 N-(6-(5,11-dioxo-5H-indeno[1,2-c]isoquinolin-6(11H)-yl)hexyl)-4-bromobenzenesulfonamide 
• 934473-89-9 C₂₈H₄₅N₅O₆ 
• 1017264-50-4 N-[(6-aminohexyl)carbamoyl]-3-methylbenzenesulfonamide 
• 1042001-96-6 C₁₃₉H₂₅₈N₂₂O₃₂ 
• 887277-38-5 tetra-(tert-butyl)-2,2',2'',2'''-{[6-(tert-butyloxycarbonylamino)hexylimino]bis(methylene)bis(4-bromopyridine-6,2-diyl)bis(methylenenitrilo)}tetrakis(acetate) 
• 884846-50-8 5-[2-(6-tert-butoxycarbonylamino-hexylcarbamoyl)-phenyl]-oxazole-4-carboxylic acid methyl ester 
• 623901-53-1 3-[(6-t-butyloxycarbamoylhexyl)amino]-1,2,4-benzotriazine 1-oxide 
• 870074-58-1 [6-(4-(hydroxymethyl)-3-nitrobenzoylamino)hexyl]carbamic acid tert-butyl ester 
• 862157-10-6 N',N''-bis(6-(tert-butoxycarbonyl)aminohexyl)-N^α-benzyloxycarbonyl-L-glutamide 

Relevant articles and documents

Water-soluble copolymeric materials: Switchable NIR two-photon fluorescence imaging agents for living cancer cells

A simple one-pot multi-component ROMP of hydrophilic, spiropyran (SP) and tert-butyloxycarbonyl-protected (Boc-protected) amino-functionalized norbornenes was developed, and a series of water-soluble copolymeric materials were provided. The photochromic SP moiety endows the copolymers the properties of switchable fluorescence imaging with alternating near-IR (NIR) two-photon and visible single-photon excitations; thereby the copolymers can serve as a promising NIR two-photon fluorescent probe for living cancer cells. The cationic ammonium group enhances the cell transporting capability of the copolymers as well. The present strategy of one-pot ROMP also makes polynorbornene a modular and flexible scaffold in designing and synthesizing specifically biocompatible polymers with applications in imaging, diagnosis and therapy. The Royal Society of Chemistry 2014.

Nanoscale photosensitizer with tumor-selective turn-on fluorescence and activatable photodynamic therapy treatment for COX-2 overexpressed cancer cells

Effective targeting andin situimaging-guided treatment are particularly important for accurate clinical photodynamic therapy (PDT) of malignant tumors. Herein, we propose a single molecule, namedIMC-DAH-SQ, which possesses dual-targeting components, including structure-inherent targeting (SIT) and cyclooxygenase-2 (COX-2) targeting units, and controllable turn-on near infrared (NIR) fluorescence. Due to its amphiphilicity,IMC-DAH-SQassembles into a nanoprobe with low background fluorescence. After incubation with tumor cells, the SIT and COX-2 recognition characteristics ofIMC-DAH-SQendow it with preferential tumor-targeting activity. The strong binding with overexpressed COX-2 can collapse the nanoprobe to monomers after accumulation in tumor cells, leading to turn-on NIR fluorescence that is completely different from normal cells. Additionally, benefiting from the single molecular model tactic, the nanoprobe has the advantages of simple synthesis without ever considering the loading rate and separation between the photosensitizer and targeting unit. Other favorite features, including superior biocompatibility, weak dark toxicity, and mitochondria enrichment capability, are implemented. All these traits not only afford nanoprobe precision tumor cell targeting capability but also provide promising imaging-guided antitumor therapy. We believe that the single molecular protocol will establish a novel strategy for simultaneous diagnosis and anticancer medicine treatment utilizing versatile but small compounds.

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Design, synthesis and anticancer activity of 2-amidomethoxy-1,4-naphthoquinones and its conjugates with Biotin/polyamine

In continuation with the previous work, a series of 5-hydroxy-2-amidomethoxy-1,4-naphthoquinones were prepared to establish the structure-activity relationship studies toward anticancer activity (IC50 in μM) against three cell lines; colo205 (colon adenocarcinoma), T47D (breast ductal carcinoma) and K562 (chronic myelogenous leukemia). Among the synthesized compounds, naphthoquinone amines, 5 (0.8; 0.6; 0.8), 14 (0.8; 0.6; 0.5) and the amine precursor, 4 (1.3; 0.3; 1.0) displayed potent anticancer activities. A tumor targeting drug delivery system was achieved by synthesizing the conjugate 6 (1.4; 0.5; 1.1) of naphthoquinone-amine 5 and Biotin which also proved its potency. Finally, to introduce polyamine conjugate, spermidine was attached with 2-amidomethoxy-1,4-naphthoquinone. The naphthoquinone-spermidine conjugate 27 (1.2; 1.7; 1.7) also retained the activity. Thus, potent naphthoquinone amines were explored and Biotin/polyamine conjugate was developed as tumor targeting drug delivery system.

Single-wall carbon nanotubes covalently linked with zinc (II) phthalocyanine bearing poly (aryl benzyl ether) dendritic substituents: Synthesis, characterization and photoinduced electron transfer

A novel series of dendritic phthalocyanine-single-wall carbon nanotube nanoconjugates, zinc (II) phthalocyanine bearing poly (aryl benzyl ether) dendritic substituents covalently linked with single-wall carbon nanotubes through either ethylenediamine or hexamethylenediamine as the spacer linker, were prepared. The structures and morphologies of the dendritic phthalocyanine-single-wall carbon nanotube nanoconjugates were characterized by IR, Raman spectroscopy, transmission electron microscopy and thermal gravimetric analysis methods. The photophysical properties of the nanoconjugates were studied by steady-state and time-resolved fluorescence spectroscopy. The intramolecular electron transfer occurred from phthalocyanine (donor) to the carbon nanotubes (acceptor) by a photoinduced process. The electron transfer exchange rate constant and the electron transfer efficacy between the dendritic phthalocyanine and single-wall carbon nanotubes increased with decreasing length of spacer linker. These novel nanoconjugates were fundamentally important due to the synergy effects of carbon nanotubes and dendritic zinc phthalocyanine, which may find potential application as biological labels.

Preparation and Preliminary Biological Evaluation of Novel 99mTc-Labelled Thymidine Analogs as Tumor Imaging Agents

Two kinds of novel thymidine derivatives, N-thymidine-yl-N′-methyl- N′-{N′′- [2-sulfanyl-(ethylamino)acetyl]-2-aminoethylsulfanyl- 1-hexanamide}-ethanediamine (TMHEA) and N-thymidine-yl-N′-methyl-N′- {N′′-[2-sulfanyl-(ethylamino)acetyl]-2- aminoethylsulfanyl-1- hexanamide}-hexanediamine (TMHHA) were prepared and successfully labeled with 99mTc in high labeling yields. The in vitro stability and in vivo biodistribution of 99mTc-TMHEA and 99mTc-TMHHA were investigated and compared. The biodistribution studies indicate that the radiotracer 99mTc-TMHEA displays selective tumor uptake, suggesting it is a potential tumor imaging agent.

Selective Pseudo-irreversible Butyrylcholinesterase Inhibitors Transferring Antioxidant Moieties to the Enzyme Show Pronounced Neuroprotective Efficacy in Vitro and in Vivo in an Alzheimer's Disease Mouse Model

A series of multitarget-directed ligands (MTDLs) was designed by functionalizing a pseudo-irreversible butyrylcholinesterase (BChE) inhibitor. The obtained hybrids were investigated in vitro regarding their hBChE and hAChE inhibition, their enzyme kinetics, and their antioxidant physicochemical properties (DPPH, ORAC, metal chelating). In addition, in vitro assays were applied to investigate antioxidant effects using murine hippocampal HT22 cells and immunomodulatory effects on the murine microglial N9 cell line. The MTDLs retained their antioxidative properties compared to the parent antioxidant-moieties in vitro and the inhibition of hBChE was maintained in the submicromolar range. Representative compounds were tested in a pharmacological Alzheimer's disease (AD) mouse model and demonstrated very high efficacy at doses as low as 0.1 mg/kg. The most promising compound was also tested in BChE-/- mice and showed reduced efficacy. In vivo neuroprotection by BChE inhibition can be effectively enhanced by incorporation of structurally diverse antioxidant moieties.

Polyamine-Conjugated Nitroxides Are Efficacious Inhibitors of Oxidative Reactions Catalyzed by Endothelial-Localized Myeloperoxidase

The heme enzyme myeloperoxidase (MPO) is a key mediator of endothelial dysfunction and a therapeutic target in cardiovascular disease. During inflammation, MPO released by circulating leukocytes is internalized by endothelial cells and transcytosed into the subendothelial extracellular matrix of diseased vessels. At this site, MPO mediates endothelial dysfunction by catalytically consuming nitric oxide (NO) and producing reactive oxidants, hypochlorous acid (HOCl) and the nitrogen dioxide radical (?NO2). Accordingly, there is interest in developing MPO inhibitors that effectively target endothelial-localized MPO. Here we studied a series of piperidine nitroxides conjugated to polyamine moieties as novel endothelial-targeted MPO inhibitors. Electron paramagnetic resonance analysis of cell lysates showed that polyamine conjugated nitroxides were efficiently internalized into endothelial cells in a heparan sulfate dependent manner. Nitroxides effectively inhibited the consumption of MPO's substrate hydrogen peroxide (H2O2) and formation of HOCl catalyzed by endothelial-localized MPO, with their efficacy dependent on both nitroxide and conjugated-polyamine structure. Nitroxides also differentially inhibited protein nitration catalyzed by both purified and endothelial-localized MPO, which was dependent on ?NO2 scavenging rather than MPO inhibition. Finally, nitroxides uniformly inhibited the catalytic consumption of NO by MPO in human plasma. These studies show for the first time that nitroxides effectively inhibit local oxidative reactions catalyzed by endothelial-localized MPO. Novel polyamine-conjugated nitroxides, ethylenediamine-TEMPO and putrescine-TEMPO, emerged as efficacious nitroxides uniquely exhibiting high endothelial cell uptake and efficient inhibition of MPO-catalyzed HOCl production, protein nitration, and NO oxidation. Polyamine-conjugated nitroxides represent a versatile class of antioxidant drugs capable of targeting endothelial-localized MPO during vascular inflammation.