13093-04-4

Usage

Uses

Used in Chemical Synthesis:
N,N'-DIMETHYL-1,6-HEXANEDIAMINE is used as an organic building block for the synthesis of various compounds, such as hydroxyurethane, which is produced by reacting DMHDA with propylene carbonate.
Used in Dental Resins:
In the dental industry, N,N'-DIMETHYL-1,6-HEXANEDIAMINE is used as a monomer to create N,N'-dimethyl, N,N'-di(methacryloxy ethyl)-1,6-hexanediamine (NDMH). NDMH serves as both a co-initiator and a reactive diluent for dental resins, enhancing their properties and performance in dental applications.
Used in Gene Transfection Vectors:
N,N'-DIMETHYL-1,6-HEXANEDIAMINE is also utilized in the production of degradable poly(amino alcohol ester) polymer by nucleophilic addition with diglycidyl adipate. This polymer has potential applications in gene transfection vectors, which are essential tools in genetic research and therapy.

Upstream product

• 629-03-8 1 ,6-dibromohexane 
• 74-89-5 methylamine 
• 629-09-4 1,6-diiodohexane 
• 1740-58-5 N,N'-dimethyl-adipamide 
• 592-42-7 1,5-Hexadien 
• 80-48-8 methyl p-toluene sulfonate 
• 47473-92-7 N,N'-dibenzenesulfonyl-1,6-diaminohexane 
• 16644-54-5 N,N'-bis(tert-butoxycarbonyl)-1,6-hexanediamine 
• 3009-40-3 N¹,N²-dibenzylidenehexane-1,6-diamine 
• 124-09-4 1,6-Hexanediamine 
• 67-56-1 methanol 
• 35161-65-0 hexanediyldiformamide 
• 111-69-3 hexanedinitrile 
• 64-17-5 ethanol 

Downstream Products

• 109-89-7 diethylamine 
• 117688-88-7 N,N''-1,6-(hexanediyl)bis[N'-cyclohexyl-N'-[(cyclohexylimino)(4-morpholinyl)methyl]-N-methylurea] 
• 112915-27-2 N,N'-Dimethyl-N,N'-hexamethylene-bis[3-(N,N-dibenzyl aminoxy)propionamide] 
• 93300-59-5 C₂₂H₂₈N₂O₂ 
• 110-89-4 piperidine 
• 111-49-9 hexamethylene imine 
• 74-89-5 methylamine 
• 109-05-7 2-Methylpiperidin 
• 157614-63-6 N-Benzyloxy-3-({6-[(2-benzyloxycarbamoyl-ethyl)-methyl-amino]-hexyl}-methyl-amino)-propionamide 
• 99191-71-6 N,N'-dimethyl-N,N'-hexanediyl-bis-carbamoyl chloride 

Relevant academic research and scientific papers

Inhibition of cellular proliferation and induction of apoptosis in human lung adenocarcinoma A549 cells by T-type calcium channel antagonist

The anti-proliferative and apoptotic activities of new T-type calcium channel antagonist, 6e (BK10040) on human lung adenocarcinoma A549 cells were investigated. The MTT assay results indicated that BK10040 was cytotoxic against human lung adenocarcinoma (A549) and pancreatic cancer (MiaPaCa2) cells in a dose-dependent manner with IC50 of 2.25 and 0.93 μM, respectively, which is ca. 2-fold more potent than lead compound KYS05090 despite of its decreased T-type calcium channel blockade. As a mode of action for cytotoxic effect of BK10040 on lung cancer (A549) cells, this cancer cell death was found to have the typical features of apoptosis, as evidenced by the accumulation of positive cells for annexin V. In addition, BK10040 triggered the activations of caspases 3 and 9, and the cleavages of poly (ADP-ribose) polymerase (PARP). Moreover, the treatment with z-VAD-fmk (a broad spectrum caspase inhibitor) significantly prevented BK10040-induced apoptosis. Based on these results, BK10040 may be used as a potential therapeutic agent for human lung cancer via the potent apoptotic activity.

In vitro cytotoxicity on human ovarian cancer cells by T-type calcium channel blockers

The growth inhibition of human cancer cells via T-type Ca2+ channel blockade has been well known. Herein, a series of new 3,4-dihydroquinazoline derivatives were synthesized via a brief SAR study on KYS05090 template and evaluated for both T-type Ca2+ channel (Ca v3.1) blockade and cytotoxicity on three human ovarian cancer cells (SK-OV-3, A2780 and A2780-T). Most of compounds except 6i generally exhibited more potent cytotoxicity on SK-OV-3 than mibefradil as a positive control regardless of the degree of T-type channel blockade. In particular, eight compounds (KYS05090, 6a and 6c-6h) showing strong channel blockade exhibited almost equal and more potent cytotoxicity on A2780 when compared to mibefradil. On A2780-T paclitaxel-resistant human ovarian carcinoma, two compounds (KYS05090 and 6d) were 20-fold more active than mibefradil. With respect to cell cycle arrest effect on A2780 and A2780-T cells, KYS05090 induced large proportion of sub-G1 phase in the cell cycle progression of A2780 and A2780-T, meaning the induction of cancer cell death instead of cell cycle arrest via blocking T-type Ca2+ channel. Among new analogues, compounds 6g and 6h induced cell cycle arrest at G1 phase of A2780 and A2780-T cells in dose-dependent manner and exhibited strong anti-proliferation effects of ovarian cancer cells by blocking T-type Ca2+ channel. Furthermore, 6g and 6h possessing strong cytotoxic effects could induce apoptosis of A2780 cells, which was detected by confocal micrographs using DAPI staining.

Use of additive sites to control nitric oxide release from nitric oxide donors contained within polymers

A method for increasing, prolonging, and/or controlling the release rates of nitric oxide (NO) from polymeric materials containing NO adducts. Such NO-containing polymeric materials may find use in devices such as blood contacting devices, and biocompatible devices utilizing the same. The method and device utilizes anionic site additives, acidic site additives and/or acidic producing site additives in a polymer that contains NO-adducts to generate higher fluxes of NO to exceed NO threshold levels desirable to substantially prevent and/or minimize reactions such as platelet activation or adhesion.

Continuous chemoselective methylation of functionalized amines and diols with supercritical methanol over solid acid and acid-base bifunctional catalysts

The selective N-methylation of bifunctionalized amines with supercritical methanol (scCH3OH) promoted by the conventional solid acids (H-mordenite, β-zeolite, amorphous silica-alumina) and acid-base bifunctional catalysts (Cs-P-Si mixed oxide and γ-alumina) was investigated in a continuous-flow, fixed-bed reactor. The use of scCH 3OH in the reaction of 2-aminoethanol with methanol (amine/CH 3OH = 1/10.8) over the solid catalysts led to a significant improvement in the chemoselectivity of the N-methylation. Among the catalysts examined, the Cs-P-Si mixed oxide provided the most efficient catalyst performance in terms of selectivity and reactivity at 300 °C and 8.2 MPa; the N-methylation selectivity in the products reaching up to 94% at 86% conversion. The present selective methylation was successfully applied to the synthesis of N-methylated amino alcohols and diamines as well as O-methylated ethylene glycol. Noticeably, ethoxyethylamine was less reactive, suggesting that the hydroxy group of the amino alcohols is a crucial structural factor in determining high reactivity and selectivity, possibly because of the tethering effect of another terminus, a hydroxo group, to the catalyst surface. The magic-angle-spinning NMR spectroscopy and X-ray diffraction analysis of the Cs-P-Si mixed oxide catalyst revealed that the acidic and basic sites originate from P2O5/SiO2 and Cs/SiO2, respectively, and the weak acid-base paired sites are attributed to three kinds of cesium phosphates on SiO2. The weak acid-base sites on the catalyst surface might be responsible for the selective dehydrative methylation.

Stereoselective aldol additions of achiral ethyl ketone-derived trichlorosilyl enolates

Methods for the preparation of geometrically defined enoxy(trichlorosilanes) derived from ethyl ketone enolates have been developed. The addition of enoxy(trichlorosilanes) (trichlorosilyl enolates) to aldehydes proceeds with good yields in the presence of catalytic amounts of chiral phosphoramides. The reaction of Z-trichlorosilyl enolates to aryl aldehydes affords aldol products with good to excellent diastereo- and enantioselectivities. Phosphoramide-catalyzed aldol additions lacked substrate generality providing modest selectivities with unsaturated and aliphatic aldehydes. In all cases, the phosphoramide-catalyzed aldol addition of E-trichlorosilyl enolates to aldehydes provided good yields with moderate to good stereoselectivities.

Chemistry of the diazeniumdiolates. 2. Kinetics and mechanism of dissociation to nitric oxide in aqueous solution

Diazeniumdiolate ions of structure R2N[N(O)NO]- (1) are of pharmacological interest because they spontaneously generate the natural bioregulatory species, nitric oxide (NO), when dissolved in aqueous media. Here we report the kinetic

Hydroboration/Amination of N-Trimethylsilyl Protected Olefinic Amines and Diolefins: Synthesis of Isomerically Pure Diamines

N-Trimethylsilyl protected olefinic amines and terminal diolefins were hydroborated with dimethylborane and the resulting organoboranes were treated with in situ generated chloramine or chloralkylamines to produce isomerically pure diamines or N-substituted diamines in good yields.