2-chloroethyl Amine Hydrochloride Research Articles

Influence of the reducing agent on the physicochemical and electrocatalytic properties of graphene-based aerogels

In-depth research was carried out with different characterization techniques (Scanning Electron Microscope (SEM), Fourier-Transform InfraRed spectroscopy (FTIR), X-ray Diffraction (XRD), picnometry, N2 adsorption/desorption) on the influence various nitrogenous and non-nitrogenous reducing agents have on the properties of graphene-based aerogels. The reducing agent used were ethylene glycol, hydrazine monohydrate, 2-chloroethylamine hydrochloride and ethylenediamine. These aerogels were synthesized by hydrothermal reduction of graphene oxide (GO) and later underwent freeze-drying. Thus, the relationship between the underlying reduction conditions with each reducing agent and certain properties such as textural and crystallographic ones and these, in turn, with electrochemical performance were elucidated.Electrocatalytic performance of the resulting graphene-based aerogels was strongly influenced by porosity, density, crystallinity and the presence of nitrogenous and oxygenated functional groups. To maximize electrocatalytic performance in the hydrogen evolution reaction (HER), a nitrogen-doped graphene aerogel with a low level of remaining oxygen functional groups, high surface mesopore area and porosity and exceptionally low density was needed. The presence of N species was found to have a positive effect on HER performance. Furthermore, adding N through hydrazine assisted hydrothermal synthesis seemed to be preferable for HER.

Hydrogen-bonded helix formation by N-brigded tripodal ligand

Hydrogen-bonded helix formation by a simple N-bridged tripodal ligand is reported. The ligand has been synthesized by reduction of product formed through substitution reaction of tris(2-chloroethyl) amine hydrochloride by hydroxybenzaldehyde. The reported ligand has been characterized by 1H NMR, 13C NMR, IR and mass spectra. Crystal structure has been characterized by single crystal X-ray diffraction and thermogravimetric analysis.

New catalysts based on reduced graphene oxide for hydrogen production from ammonia decomposition

Promising and highly novel catalysts based on ruthenium (Ru) supported on reduced graphene oxide were synthesized, characterized and tested for COx-free hydrogen generation by catalytic ammonia decomposition. Metal loading and amount of a pre-reducing agent clearly affect the catalytic properties of the final catalysts. A Ru loading higher than 2.5 wt% resulted in Ru particles of size higher than 5 nm, which were agglomerated, thus decreasing the amount of the most active sites (B5 type-sites) and therefore the ammonia conversion. Additionally, a graphene oxide (GO) hydrothermal pre-reduction with 2-chloroethylamine hydrochloride, led materials with a more ordered structure which is associated with a good electronic conductivity and, higher basicity. Optimal catalytic activity is achieved using a reducing agent/GO ratio of 5/3 (wt/wt) and a Ru loading of 2.5 wt%. Thus, 2.5Ru/10C-rGO catalyst resulted in excellent hydrogen (H2) production from ammonia decomposition, with an ammonia conversion close to 96% and hydrogen production rate of 9.1 mmolH2 gcat−1 min−1 at 400 °C. Reduced graphene oxide proved to be a suitable support in the development of nanosized Ru catalysts being the optimal one highly active in COx-free hydrogen generation during more than 60 h of reaction, providing virtuous stability.

Green and facile synthesis of aminated lignin-silver complex and its antibacterial activity

Silver nanoparticles (AgNPs) exhibit broad spectrum antibacterial effect, but their cores after use can persist in the environment, which presents a toxic effect on humans. To address this issue, silver-based biomaterials are regarded as green alternatives to AgNPs. In this study, we used kraft lignin, a green and biodegradable polymer derived from wood biomass, to prepare an aminated lignin-silver complex (Ag@AL complex) as an alternative antibacterial agent. A facile approach for preparing aminated lignin (AL) was realized by the amination of kraft lignin using 2-chloroethylamine hydrochloride in water solvent. The nitrogen content of optimized AL was 4.37 %. Ag(Ⅰ) could be captured and reduced to metallic Ag(0) by AL, thereby forming AgNPs on the surface of AL. Importantly, the obtained Ag@AL complex was proven to be an effective antibacterial agent against gram-positive (Bacillus cereus, Staphylococcus aureus) and gram-negative (Salmonella enterica) bacteria.

Synthesis and acaricidal activity of phenylpiperazine derivatives.

We synthesized 33 new phenylpiperazine derivatives and assessed their acaricidal activity. These derivatives were synthesized through sequential reactions consisting of the sulfonylation of 2-substituted 4-methylaniline with chlorosulfonic acid, reduction with red phosphorus and iodine, alkylation by alkyl halide, cyclization with bis(2-chloroethyl)amine hydrochloride, and N-substitution reaction of phenylpiperazines with various reagents. All phenylpiperazines synthesized were evaluated for acaricidal activity and their structure–activity relationships discussed, it was found that 4-substituted 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]piperazine derivatives exhibited good acaricidal activity. Among them, 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-4-(trifluoromethylsulfonyl) piperazine showed the highest level of activity against Tetranychus urticae and provided a high level of activity against Tetranychus kanzawai and Panonychus citri. In addition, studies on the effect at various stages of T. urticae exhibited that this compound showed good activity against both adults and eggs.

Chitosan hydrogels cross-linked with tris(2-(2-formylphenoxy)ethyl)amine: Swelling and drug delivery

Tris(2-(2-formylphenoxy)ethyl)amine was designed and synthesized by reaction of salicylaldehyde with tris(2-chloroethyl)amine hydrochloride and evaluated as a new multi-functional cross-linker for preparation of new pH- and thermo-responsive chitosan hydrogels through formation of covalent Schiff-base linkage. The structure and properties of the hydrogels were characterized by FT-IR, 1H NMR and scanning electron microscopy (SEM). The swelling behavior of prepared hydrogels at different pHs and temperatures was investigated. Also, in vitro controlled release behavior of the metronidazole model drug was studied with prepared hydrogels. The release profiles of metronidazole from the hydrogels were determined by UV–Vis absorption measurement. The results showed that the new hydrogels exhibit a pH and temperature-responsive swelling ratio. Also, the pH and temperature were found to strongly influence the drug release behavior of these swollen polymers. Due to the concurrent rapid and significant stimuli-response, these smart hydrogels prepared from chitosan as a natural polymer may expand the scope of hydrogel applications in various fields of research such as targeted (cellular or tissue) delivery of drugs. In addition, these new hydrogels can be used to improve bioavailability, sustain release of drugs or solubilize drugs for systemic delivery.

Preparation and characterization of aminoethyl hydroxypropyl starch modified with collagen peptide

The preparation of aminoethyl hydroxypropyl starch collagen peptide (AEHPS-COP) was via an enzyme-catalyzed reaction between amino groups in aminoethyl hydroxypropyl starch (AEHPS) and γ-carboxamide groups in collagen peptide (COP) by using microbial transglutaminase (MTGase) as biocatalyst. As an intermediate reactant, AEHPS was synthesized from hydroxypropyl starch (HPS) and 2-chloroethylamine hydrochloride (CEH). The chemical structures of HPS, AEHPS and AEHPS-COP were characterized by Fourier transform infrared spectroscopy (FT-IR) and 13C nuclear magnetic resonance (13C NMR). The reaction conditions that influenced the degree of substitution (DS) of AEHPS-COP were optimized, which included the reaction temperature, the reaction time, the mass ratio of collagen peptide to aminoethyl hydroxypropyl starch and the pH value. In addition, in vitro antioxidant activities of AEHPS-COP were evaluated through the scavenging activity of hydroxyl and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. Furthermore, the methylthiazol tetrazolium (MTT) assay was applied to investigate the cell viability of AEHPS-COP. The results indicated that the AEHPS-COP exhibited better cell viability to L929 mouse fibroblast cells. Therefore, the AEHPS-COP showed a promising potential application in cosmetic, biomedical and pharmaceutical fields.

Nitrogen Doped Graphene as Potential Material for Hydrogen Storage

The nitrogen doped graphene was synthesized by hydrothermal route utilizing 2-Chloroethylamine hydrochloride as nitrogen precursor in the presence of graphene oxide (GO). Nitrogen-doped graphene material is developed for its application in hydrogen storage at room temperature. Nitrogen doped graphene layered material shows ~1.5 wt% hydrogen storage capacity achieved at room temperature and 90 bar pressure.

Preparation and characterization of aminoethyl hydroxypropyl methyl cellulose modified with nisin

Nisin grafted aminoethyl hydroxypropyl methyl cellulose (AEHPMC) was prepared by an enzyme-catalyzed reaction in the presence of microbial transglutaminase (MTGase). AEHPMC was synthesized with 2-chloroethylamine hydrochloride (CEH) which was as an intermediate reactant. The parameters, which influenced the NH2% and the degree of substitution (DS), including reaction time, reaction temperature and the mass ratio of the reactants were investigated. Antioxidant activities of AEHPMC-nisin were evaluated by the scavenging activity of hydroxyl and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. With the DS and concentration increasing of AEHPMC-nisin, the radical scavenging activity increased. The Methylthiazol tetrazolium (MTT) assay indicated that AEHPMC-nisin had low-toxicity to L929 cells. Therefore, the derivative of HPMC may show a promising potential application in biomedical, food and pharmaceutical fields.

Chrysin-piperazine conjugates as antioxidant and anticancer agents

Synthesis of 7-(4-bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one intermediate treating chrysin with 1,4-dibromobutane facilitated combination of chrysin with a wide range of piperazine moieties which were equipped via reacting the corresponding amines with bis(2-chloroethyl)amine hydrochloride in diethylene glycol monomethyl ether solvent. Free radical scavenging potential of prepared products was analyzed in vitro adopting DPPH and ABTS bioassay in addition to the evaluation of in vitro anticancer efficacies against cervical cancer cell lines (HeLa and CaSki) and an ovarian cancer cell line SK-OV-3 using SRB assay. Bearable toxicity of 7a-w was examined employing Madin-Darby canine kidney (MDCK) cell line. In addition, cytotoxic nature of the presented compounds was inspected utilizing Human bone marrow derived mesenchymal stem cells (hBM-MSCs). Overall, 7a-w indicated remarkable antioxidant power in scavenging DPPH· and ABTS·+, particularly analogs 7f, 7j, 7k, 7l, 7n, 7q, 7v, 7w have shown promising free radical scavenging activity. Analogs 7j and 7o are identified to be highly active candidates against HeLa and CaSki cell lines, whereas 7h and 7l along with 7j proved to be very sensitive towards ovarian cancer cell line SKOV-3. None of the newly prepared scaffolds showed cytotoxic nature toward hBM-MSCs cells. From the structure–activity point of view, nature and position of the electron withdrawing and electron donating functional groups on the piperazine core may contribute to the anticipated antioxidant and anticancer action. Different spectroscopic techniques (FT-IR, 1H NMR, 13C NMR, Mass) and elemental analysis (CHN) were utilized to confirm the desired structure of final compounds.

Switching Dielectric Constant Near Room Temperature in a Molecular Crystal.

The organic salt bis(2-chloroethyl)amine hydrochloride shows a sharp switching of its dielectric constant at 320 K. The switching property originates from the dynamic changes of the (2-chloroethyl)ammonium cation between frozen and motional states, corresponding to a structural phase transition.

Development of hybrid-type modified chitosan derivative nanoparticles for the intracellular delivery of midkine-siRNA in hepatocellular carcinoma cells

Hepatocellular carcinoma (HCC) is one of the most common cancers worldwide. Most of the patients with HCC lose the surgical opportunity at the time of diagnosis. Some novel therapeutic modalities, like gene therapy, are promising for the treatment of HCC. However, the success of gene therapy depends on two aspects: efficient gene materials and gene delivery vectors. The present study was to develop new chitosan-based nanoparticles for a midkine-siRNA (anti-HCC gene drug) delivery. The novel gene delivery vector (MixNCH) was synthesized by hybrid-type modification of chitosan with 2-chloroethylamine hydrochloride and N, N-dimethyl-2-chloroethylamine hydrochloride. The chemical structure of MixNCH was characterized by FT-IR and 1HNMR. The cytotoxicity of MixNCH was determined by MTS assay. The gene condensation ability and size, zeta potential and morphology of MixNCH/MK-siRNA nanoparticles were measured. The in vitro transfection and gene knockdown efficiency of midkine by MixNCH/MK-siRNA nanoparticles was detected by qRT-PCR and Western blotting. Gene knockdown effect at the molecule level on the proliferation of HepG2 in vitro was determined by MTS assay. MixNCH was successfully acquired by aminoalkylation modification of chitosan. The MixNCH could condense MK-siRNA well above the weight ratio of 3. The average size of MixNCH/MK-siRNA nanoparticles was 100-200 nm, and the surface charge was about +5 mV. Morphologically, MixNCH/MK-siRNA nanoparticles were in regular spherical shape with no aggregation. Regarding to the in vitro transfection of nanoparticles, the MixNCH/MK-siRNA nanoparticles reduced MK mRNA level to 14.03%+/-4.03%, which were comparable to Biotrans (8.94%+/-3.77%). MixNCH/MK-siRNA effectively inhibited the proliferation of HepG2 in vitro. MixNCH/MK-siRNA nanoparticles could be effective for the treatment of hepatocellular carcinoma.

Synthesis, docking and biological activities of novel hybrids celecoxib and anthraquinone analogs as potent cytotoxic agents.

Herein, novel hybrid compounds of celecoxib and 2-aminoanthraquinone derivatives have been synthesized using condensation reactions of celecoxib with 2-aminoanthraquinone derivatives or 2-aminoanthraquinon with celecoxib derivatives. Celecoxib was reacted with different acid chlorides, 2-chloroethylisocyanate and bis (2-chloroethyl) amine hydrochloride. These intermediates were then reacted with 2-aminoanthraquinone. Also the same different acid chlorides and 2-chloroethylisocyanate were reacted with 2-aminoanthraquinone and the resulting intermediates were reacted with celecoxib to give isomers for the previous compounds. The antitumor activities against hepatic carcinoma tumor cell line (HEPG2) have been investigated in vitro, and all these compounds showed promising activities, especially compound 3c, 7, and 12. Flexible docking studies involving AutoDock 4.2 was investigated to identify the potential binding affinities and the mode of interaction of the hybrid compounds into two protein tyrosine kinases namely, SRC (Pp60v-src) and platelet-derived growth factor receptor, PDGFR (c-Kit). The compounds in this study have a preferential affinity for the c-Kit PDGFR PTK over the non-receptor tyrosine kinase SRC (Pp60v-src).

Labeled oxazaphosphorines for applications in mass spectrometry studies. 2. Synthesis of deuterium‐labeled 2‐dechloroethylcyclophosphamides and 2‐ and 3‐dechloroethylifosfamides

The prodrugs cyclophosphamide (CP) and ifosfamide (IF) each metabolize to an active alkylating agent through a cytochrome P450-mediated oxidation at the C-4 position. Competing with this activation pathway are enzymatic oxidations at the exocyclic α and α' carbons, which result in dechloroethylation of CP and IF. The incidence of oxidation at one position relative to another is believed to be at least one factor underlying the high degree of interpatient variability in both CP and IF pharmacokinetics. As standards for the mass spectrometry quantification of dechloroethylation, the following were synthesized: (1) [4,4,5,5-(2) H4 ]-2-dechloroethylcyclophosphamide (equivalent to [4,4,5,5-(2) H4 ]-3-dechloroethylifosfamide); (2) [α,α,4,4,5,5-(2) H6 ]-2-dechloroethylcyclophosphamide (equivalent to [α,α,4,4,5,5-(2) H6 ]-3-dechloroethylifosfamide); and (3) [α,α,4,4,5,5-(2) H6 ]-2-dechloroethylifosfamide. The common precursor to all of the target compounds was [2,2,3,3-(2) H4 ]-3-aminopropanol. A one-pot reaction of this compound with POCl3 and unlabeled or labeled 2-chloroethylamine hydrochloride gave the d4 and d6 labeled 2-dechloroethylcyclophosphamides. The construction of the 2-dechloroethylifosfamide from the aminopropanol required five discreet steps. Optimization of the synthetic pathways and stability studies are discussed.

N, N- bis (2-CHLOROETHYL)AMIDES AND N, N- bis (2-CHLOROETHYL)HYDRAZIDES OF CARBOXYLIC ACIDS OF THE FURAN SERIES

Reaction of N, N-bis(2-chloroethyl)amine hydrochloride with chloroanhydrides of carboxylic acids of the furan series, in chloroform in the presence of pyridine gives N, N-bis(2-chloroethyl)amides of furan carboxylic acid, furylacrylic acid, 5-nitrofuran carboxylic acid, and 5-nitrofurylacrylic acid. N, N-bis(2-chloroethyl)hydrazides of furan carboxylic acid, furyl carboxylic acid, 5-nitrofuran carboxylic acid, and 5-nitrofurylacrylic acid were obtained in 78–88% yields by reacting N, N-bis(2-chloroethyl)hydrazine hydrochloride with the chloroanhydrides of the appropriate acids in chloroform in the presence of pyridine. The last two hydrazides were prepared in 31 % and 56 % yield, respectively, using anhydrous sodium acetate in place of pyridine. Authors: B. V. Kurgan, S. A. Giller, A. A. Gruze. English Translation in Chemistry of Heterocyclic Compounds , 1965, 1 (1), pp 5-7 http://link.springer.com/article/10.1007/BF01168908

Synthesis and characterization of glycosylated nitrogen mustard derivatives and their interaction with bovine serum albumin

To improve the specificity of nitrogen mustards towards tumor cells, glucose-nitrogen mustard, fructose-nitrogen mustard, and lactose-nitrogen mustard were prepared as three novel glycosylated nitrogen mustard derivatives by esterification of bis(2-chloroethyl)carbamic chloride (BCC) with glucose, fructose, and lactose, respectively. BCC was synthesized from bis(2-chloroethyl)amine hydrochloride and triphosgene. The topic products were characterized by infrared (IR) and mass spectrometry (MS), and their interaction with bovine serum albumin was investigated by measuring fluorescence spectra in tris(hydroxymethyl)aminomethane hydrochloride (Tris–HCl) buffer solution at physiological conditions.

Synthesis, photophysical, and electrochemical properties of a new family of trinuclear Ru(II) polypyridine complexes

A series of four tripodal ligands L1–4 were prepared by the reaction of 9-(2-hydroxy)phenylimino-4,5-diazafluorene with 1,3,5-tris(bromomethyl)benzene, 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene, tris(2-chloroethyl)amine hydrochloride, and pentaerythrityl tetratosylate, respectively, in DMF solution under nitrogen. For each ligand, Ru(II) complexes were prepared by refluxing Ru(bipy)2Cl2 · 2H2O and ligand in 2-methoxyethanol. Photophysical behaviors of these Ru(II) complexes have been investigated by UV-Vis absorption and luminescence spectrometry. They display metal-to-ligand charge transfer absorption at 442 nm in MeCN solution at room temperature and emission at 574 nm in EtOH–MeOH (4 : 1, v/v) glassy matrix at 77 K. Electrochemical studies of the Ru(II) complexes show one Ru(II)-centered oxidation at 1.33 V and three ligand-centered reductions.

ChemInform Abstract: One‐Pot Synthesis of Functionalized Tetrahydro‐1,4‐thiazepines.

AbstractTitle compounds (IV) are obtained via two different routes via a shared intermediate.

One-Pot Synthesis of Functionalized Tetrahydro-1,4-thiazepines

One-pot synthesis of (5Z,7Z)-5-amino-7-(ethyl or arylimino)-2,3,4,7-tetrahydro-1,4-thiazepine-6-carbonitriles from cyclocondensation of 2-((ethyl or arylamino)(mercapto)methylene)malononitrile potassium salts or their methylated derivatives with 2-chloroethylamine hydrochloride or cysteamine in dimethylformamide via two routes but a single intermediate is described.

A Convenient Synthesis of N-Functionalized Perfluoroalkanesulfonamides

This article describes the synthesis of new N-functionalized perfluoroalkanesulfonamides (5) with two sulfonamides functionalities. Perfluoroalkanesulfonyl fluoride underwent a reaction with 2-chloroethylamine hydrochloride or 3-bromopropylamine hydrobromide to give N-(2-chloroethyl or 3-bromopropyl) perfluoroalkanesulfonamides (1). Reaction of (1) with potassium thiocyanate gave N-(2-thiocyanatoethyl or 3-thiocyanatopropyl) perfluoroalkanesulfonamides (3). The sulfonyl chloride derivatives (4) were prepared by reaction of 3 with sulfuryl chloride. In the last step, 4 reacted with ammonia to give the bis sulfonamides derivatives (5). The structures of all new compounds prepared were determined by 1H, 19F, and 13C NMR spectroscopies and by HR-MS.