Chloride Derivatives Research Articles

Synthetic (E)-3-Phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium Chloride Derivatives as Promising Chemotherapy Agents on Cell Lines Infected with HTLV-1.

Synthesis of four compounds belonging to mesoionic class, (E)-3-phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium chloride derivatives (5a–d) and their biological evaluation against MT2 and C92 cell lines infected with human T-cell lymphotropic virus type-1 (HTLV-1), which causes adult T-cell leukemia/lymphoma (ATLL), and non-infected cell lines (Jurkat) are reported. The compounds were obtained by convergent synthesis under microwave irradiation and the cytotoxicity was evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays. Results showed IC50 values of all compounds in the range of 1.51–7.70 μM in HTLV-1-infected and non-infected cells. Furthermore, it was observed that 5b could induce necrosis after 24 h for Jurkat and MT2 cell lines. The experimental (fluorimetric method) and theoretical (molecular docking) results suggested that the mechanism of action for 5b could be related to its capacity to intercalate into DNA. Moreover, the preliminary pharmacokinetic profile of the studied compounds (5a–d) was obtained through human serum albumin (HSA) binding affinity using multiple spectroscopic techniques (circular dichroism, steady-state and time-resolved fluorescence), zeta potential and molecular docking calculations. The interaction HSA:5a–d is spontaneous and moderate (Ka ~ 104 M−1) via a ground-state association, without significantly perturbing both the secondary and surface structures of the albumin in the subdomain IIA (site I), indicating feasible biodistribution in the human bloodstream.

Synthesis of Some New Pyrazoline-Based Thiazole Derivatives and Evaluation of Their Antimicrobial, Antifungal, and Anticancer Activities

3-(2-Thienyl)-5-aryl-1-thiocarbamoyl-2-pyrazolines were reacted with chloroacetone derivatives and hydrazonyl chloride derivatives in ethanol to afford the corresponding thiazolylpyrazoline derivatives and thiophenylpyrazolyl-5-substituted aryl-diazenylthiazole derivatives, respectively. The structures of the newly synthesized compounds were elucidated by different elemental and spectral analyses (IR, mass, 1H and 13C NMR). The antimicrobial and antifungal activities of the newly synthesized compounds were evaluated against four bacterial species and five fungal strains. In addition, the antitumor activities of two of the newly synthesized compounds 1-(2-(5-(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazol-1-yl)-4-methyl thiazol-5-yl)ethan-1-one and 2-(5-(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methyl-5-(phenyl-diazenyl)thiazole against HEPG-2, HCT-116, MCF-7, BHK, and CACO-2 were evaluated. From the obtained results, we found that these two compounds were the most potent candidates towards all gram-positive and gram-negative bacteria, as well as the fungi studied. Also, the same two compounds showed strong antitumor activities against two of the tumor cell lines (HCT-116 and CACO-2).

Synthesis and Reactivity of Organometallic Intermediates Relevant to Cobalt-Catalyzed Hydroformylation.

Intermediates relevant to cobalt-catalyzed alkene hydroformylation have been isolated and evaluated in fundamental organometallic transformations relevant to aldehyde formation. The 18-electron (R,R)-(iPr DuPhos)Co(CO)2 H has been structurally characterized, and it promotes exclusive hydrogenation of styrene in the presence of 50 bar of H2 /CO gas (1:1) at 100 °C. Deuterium-labeling studies established reversible 2,1-insertion of styrene into the Co-D bond of (R,R)-(iPr DuPhos)Co(CO)2 D. Whereas rapid β-hydrogen elimination from cobalt alkyls occurred under an N2 atmosphere, alkylation of (R,R)-(iPr DuPhos)Co(CO)2 Cl in the presence of CO enabled the interception of (R,R)-(iPr DuPhos)Co(CO)2 C(O)CH2 CH2 Ph, which upon hydrogenolysis under 4 atm H2 produced the corresponding aldehyde and cobalt hydride, demonstrating the feasibility of elementary steps in hydroformylation. Both the hydride and chloride derivatives, (X=H- , Cl- ), underwent exchange with free 13 CO. Under reduced pressure, (R,R)-(iPr DuPhos)Co(CO)2 Cl underwent CO dissociation to form (R,R)-(iPr DuPhos)Co(CO)Cl.

Synthesis and Reactivity of Organometallic Intermediates Relevant to Cobalt‐Catalyzed Hydroformylation

AbstractIntermediates relevant to cobalt‐catalyzed alkene hydroformylation have been isolated and evaluated in fundamental organometallic transformations relevant to aldehyde formation. The 18‐electron (R,R)‐(iPrDuPhos)Co(CO)2H has been structurally characterized, and it promotes exclusive hydrogenation of styrene in the presence of 50 bar of H2/CO gas (1:1) at 100 °C. Deuterium‐labeling studies established reversible 2,1‐insertion of styrene into the Co−D bond of (R,R)‐(iPrDuPhos)Co(CO)2D. Whereas rapid β‐hydrogen elimination from cobalt alkyls occurred under an N2 atmosphere, alkylation of (R,R)‐(iPrDuPhos)Co(CO)2Cl in the presence of CO enabled the interception of (R,R)‐(iPrDuPhos)Co(CO)2C(O)CH2CH2Ph, which upon hydrogenolysis under 4 atm H2 produced the corresponding aldehyde and cobalt hydride, demonstrating the feasibility of elementary steps in hydroformylation. Both the hydride and chloride derivatives, (X=H−, Cl−), underwent exchange with free 13CO. Under reduced pressure, (R,R)‐(iPrDuPhos)Co(CO)2Cl underwent CO dissociation to form (R,R)‐(iPrDuPhos)Co(CO)Cl.

Thienyl Chloride Initiated Living Cationic Polymerization: A General and Efficient Access toward Terminally Functionalized Poly(vinyl ether)s

Poly(vinyl ether)s (PVEs) are useful materials of different applications. In this work, we have developed a versatile and highly efficient initiation approach based on thienyl chloride derivatives ...

Design, Synthesis, and Biological Activity of Novel Diazabicyclo Derivatives as Safeners.

Herbicide safeners selectively protect crops from herbicide damage without reducing the herbicidal efficiency on target weed species. The title compounds were designed by the intermediate derivatization approach and fragment splicing to exploit novel potential safeners. A total of 31 novel diazabicyclo derivatives were synthesized by the microwave-assistant method using isoxazole-4-carbonyl chloride and diazabicyclo derivatives. All synthetic compounds were confirmed by infrared, 1H and 13C nuclear magnetic resonance, and high-resolution mass spectrometry. The bioassay results demonstrated that most of the title compounds could reduce the nicosulfuron phytotoxicity on maize. The glutathione S-transferase (GST) activity in vivo was assayed, and compound 4(S15) revealed an inspiring safener activity comparable to commercialized safeners isoxadifen-ethyl and BAS-145138. The molecular docking model exhibited that the competition at the active sites of target enzymes between compound 4(S15) and nicosulfuron was investigated with respect to herbicide detoxification. The current work not only provided a powerful supplement to the intermediate derivatization approach and fragment splicing in design pesticide bioactive molecules but also assisted safener development and optimization.

Synthesis and anticancer evaluation of N-benzoyl-N'-phenyltiourea derivatives against human breast cancer cells (T47D)

New anti-breast cancer compounds have been found and may prove to have stronger activity. To predict the activities of N-benzoyl-N'-phenylthiourea (BPTU) derivatives, namely N-(3-chloro)benzoyl-N'-phenylthiourea (3-Cl-BPTU) and N-(3,4-dichloro)benzoyl-N'-phenylthiourea (3,4-2Cl-BPTU) with Sirtuin-1 receptor (PDB code: 4I5I), molecular docking was conducted at the beginning of this study. The compounds were then synthesized from benzoyl chloride derivatives and N-phenylthiourea. Molecular structure was confirmed using FTIR, 1H NMR, 13C NMR and Mass Spectra, while the anticancer activity was tested in vitro against human breast cancer cells (T47D) using MTT assay. The results indicated that the anti-cancer activities of the test compounds were better than those of the hydroxyurea as the reference compound, evidenced by the Rerank Score (RS). Furthermore, cytotoxic effect of 3-Cl-BPTU (IC50: 0.43 mM) and 3,4-dichloro-BPTU (IC50: 0.85 mM) showed better result compared with hydroxyurea (IC50: 4.58 mM). Therefore, we concluded that these compounds could possess termendous potential as the candidate for a new anticancer drug.

Thiazole Azodyes Containing Sulfonamide Moiety for UV Protection and Antimicrobial of Cotton Fabrics

Hot three 4-(5-methyl-4-(1-(2-(4-methyl-5-(aryldiazenyl)thiazol-2-yl)hydrazono)ethyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamides were designed by interacting of 4-(4-acetyl-5-methyl-1H-1,2,3-triazol-1-yl)benzenesulfonamide with thiosemicarbazide succeed by reacting the output with several hydrazonoyl chloride derivatives in slightly basic-ethanol under reflux terms. The fresh products are distinguished and utilized as azo dyes for simultaneous dyeing and easy patronage finishing of cotton textile to reinforce the dyeability in addition to practical advantages of that fabric. The scores disclosed that the dyed-finished fabric samples have perfect fastness besides effectual properties, that is, UV protection and antibacterial properties. Over and above, the cured fabric was described, contrast with untreated sample, via SEM and EDX analysis.

A facile synthetic route and dual function of network luminescent porous polyester and copolyester containing porphyrin moiety for metal ions sensor and dyes adsorption

Abstract In this work, A novel optical metal ion sensor microporous polyesters and copolyesters containing porphyrin moiety as a monomeric unit in the main chain were successfully prepared by the interfacial condensation polymerization from 5,10,15,20-Tetrakis(4-hydroxyphenyl) porphyrin (Por-OH) and 5,10,15,20-Tetrakis(4-hydroxy-3-methoxyphenyl) porphyrin (Por-V) with aliphatic and aromatic acid chlorides derivatives (such as; adipoyl chloride, and azobenzene-4,4′-dicarboxylic chloride, respectively). These polyesters and copolyesters are characterized by FT-IR, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), X-ray diffraction, UV–Visible absorbance, fluorescence emission, and SEM measurements. The results show that our novel compounds are amorphous, have good thermal stability with high char yield and possess peaks similar to the porphynoid structure that make them good metal ion sensors with different metals ions (such as; Zn+2, Cu+2, Ni+2, Co+2, and Fe+3). Also, they can be used as dye adsorbents in aqueous solution and displayed amazing adsorption and selectivity toward cationic dye methylene blue (MB) over anionic sunset yellow (SY) in the dye's mixture.

Catalytic and antibacterial properties of 3‐dentate carboxamide Pd/Pt complexes obtained via a benign route

The complexes PdII(qcq)(OAc) and PtII(qcq)Cl have been synthesized using environmentally benign synthesized ligands and characterized by elemental analyses: Fourier transform infrared spectroscopy, UV–visible spectroscopy, 1H NMR spectroscopy, and X‐ray diffraction. The catalytic activity of the complex was assessed, in different media, for the Mizoroki–Heck coupling reaction for typical aryl halides and terminal olefins under aerobic conditions. Since the base and the solvent were found to influence the efficiency of the reaction, reaction conditions, temperature, time, and the amount of K3PO4 and a mixture of H2O/PEG, were optimized. We found, for the Mizoroki–Heck reaction coupling less reactive aryl chloride derivatives with olefins, promising activity for palladium catalysts. The electrochemical behavior of Hqcq and the Pd(II) complex was investigated by cyclic voltammetry and irreversible PdII/I reductions were observed. Hqcq and the Pd(II) and Pt(II) complexes were also screened for their in vitro antibacterial activity. They showed promising antibacterial activity comparable to that of the antibiotic penicillin.

ABL1 kinase inhibitors for the treatment of Niemann-Pick disease type A

An attempt has been made to delineate the role of natural and synthetic retinoid receptor ligands on vimentin expression in the human triple-negative breast cancer cells. The effects of currently synthesized triorganotin derivatives of the general formula R3SnX (R is butyl or phenyl, X is isothiocyanate), which are considered RXR ligands, were investigated in the human MDA-MB-231 breast cancer cell line. Studies were evaluated in the presence and absence of all-trans retinoic acid (ATRA), a natural RAR ligand. Vimentin represents the major protein associated with epithelial-mesenchymal transition (EMT), an essential process when the primary tumour transforms into a malignant one. mRNA and proteomic data obtained in this study, based on the PDQuest software protein evaluation and further quantification of proteins by iTRAQ analysis, suggest that vimentin was significantly reduced in the combination of RAR ligand and RXR ligand treatment. Both tested triorganotin compounds showed similarly reduced expression of vimentin, but tributyltin isothiocyanate (TBT-ITC) proved to be more effective than triphenyltin isothiocyanate (TPT-ITC). Furthermore, the effect of natural (9cRA) and synthetic RXR ligands, both chloride and isothiocyanate derivatives, on vimentin expression was compared.

Synthesis, properties and biodegradation of periodic copolyesters composed of hydroxy acids, ethylene glycol, and terephthalic acid

Aromatic polyesters such as poly(ethylene terephthalate) (PET), poly(trimethylene terephthalate) (PTT) and poly(butylene terephthalate) (PBT) are widely used all over the world due to their excellent physical properties. However, their degradation in the environment is very slow and the environmental load of their wastes is a potential problem. On the other hand, poly(l-lactic acid) (PLLA) and poly(glycolic acid) (PGA) have attracted attention for their biodegradability. We expected that periodic copolyesters composed of hydroxy acids, ethylene glycol, and terephthalic acid can be biodegradable polymer with relatively high melting points. In this study, a series of novel periodic copolyesters was synthesized and their physical properties and biodegradabilities were investigated. The 2:1 condensation products (LEL and GEG) of l-lactic acid (LA) or glycolic acid (GA) and ethylene glycol were synthesized from the reaction of potassium salt of LA or GA with 1,2-dibromoethane. Then, the polycondensation of LEL or GEG with chloride derivatives of dicarboxylic acids (terephthalic acid, 2,5-furandicarboxylic acid, 2,6-naphthalenedicarboxylic acid, and adipic acid) were performed to produce a series of periodic copolyesters such as poly((ethylene diglycolate) terephthalate) (poly(GEGT)) and poly((ethylene di(l-lactate)) terephthalate) (poly(LELT)). The most of the copolyesters with LA units such as poly(LELT) were amorphous. In contrast, the copolyesters with GA units exhibited relatively high melting temperature (e.g. Tm = 209 °C for poly(GEGT)). The preliminary degradation tests of poly(GEGT) and poly(LELT) were performed. The obtained poly(GEGT) showed biodegradability in seawater at 27 °C.

Deep eutectic solvents consisting of 1-ethyl-3-methylimidazolium chloride and glycerol derivatives for highly efficient and reversible SO2 capture

Development of eco-friendly materials for the removal of SO2 is a significant topic in sustainable chemical engineering process. In this work, we describe an efficient protocol for highly efficient and reversible SO2 capture by deep eutectic solvents (DESs) consisting of 1-ethyl-3-methylimidazolium chloride (EmimCl) and glycerol derivatives. The presented DESs exhibit an equal or much higher absorption capacity than previously reported DESs or ionic liquids in the same conditions. Particularly, EmimCl-glycerol (molar ratio 2:1) shows excellent reversible absorption through physical interactions supporting by FTIR and NMR spectroscopic experiments, thus presenting good potential as a candidate absorbent for the removal of SO2.

An Efficient Palladium-Catalysed Aminocarbonylation of Benzyl Chlorides

An improved procedure for the aminocarbonylation of benzyl chloride derivatives using carbon monoxide and either primary or secondary amines has been developed. Studying the competing background alkylation reaction allowed the solvent and base to be selected for a simple catalyst screen, which, in turn, enabled the discovery of a method for the preparation of 2-arylacetamides under mild conditions, with minimal side-products using an inexpensive phosphine ligand. This non-traditional optimisation strategy allowed us to overcome the background alkylation, which has been cited as justification for the development of more complex and less atom-economical approaches.

Intermolecular Interactions and Intramolecular Couplings of Binuclear Porphyrin Models for Cytochrome c Oxidase.

Cytochrome c oxidase (CcO) has a binuclear active site composed of a high-spin heme group and a tris-histidine-ligated copper ion (CuB). By using two different porphyrin models derived by Gunter (H2TPyPP) and us (H2TImPP), we have isolated several mono- and binuclear complexes including one carbonyl and three chloride derivatives which are determined by 100 K single-crystal X-ray. Low-temperature (4 K) EPR and multitemperature (295-25 K) Mössbauer investigations on the products not only confirmed the spin states of the two metal ions (S = 5/2 Fe3+ and S = 1/2 Cu2+) but also revealed the intermolecular interactions and intramolecular couplings which are in accordance with the crystal structural features.

Molecular structure of 1,4-bis(substituted-carbonyl)benzene: A combined experimental and theoretical approach

The reaction of pyrazole derivatives (pyrazole (Pz), 3-methylpyrazole (MPz) and 3,5-dimethylpyrazole (DMPz)) with terephthaloyl dichloride (TD) in the presence of Et3N afforded the desired products, 1,4-bis(pyrazolylcarbonyl)benzene (1), 1,4-bis(3-methylpyrazolylcarbonyl)benzene (2) and 1,4-bis(3,5-dimethylpyrazolylcarbonyl)benzene (3).Good quality crystals were isolated and diffraction data for single crystal were collected which revealed that compounds 1–3 are monoclinic with space group P21/n, C2/c and P21/c, respectively. These compounds were obtained as a result of C–N coupling reaction between the acid chloride and pyrazol derivatives with the intent to explore their structure in solution as well as solid state. Density function theory (DFT) calculations using B3LYP and CAM-B3LYP functionals with 6-311G(d,p) basis set were performed to explore geometric and electronic properties of compounds. The Root Mean Square Error (RMSE) has also been calculated for the values of geometric parameters, indicating a good agreement with experimental findings. Moreover, frontier molecular orbitals (FMOs) and natural bond orbitals (NBOs) analyses were carried out through B3LYP/6-311G(d,p) level of theory. The linear polarizability (α) values of nonlinear optical (NLO) analysis were calculated with the same level of theory and basis set as FMO but under different solvent conditions. Time Dependent Density Functional Theory (TD-DFT) study of these pyrazole substituted derivatives was performed aiming to investigate UV–Visible behavior. The stability of molecule has been additionally analyzed by Hirshfeld surface analysis in addition to NBO analysis. The calculated HOMO and LUMO energies from FMO assisted in calculating global reactivity parameters (Chemical hardness, chemical softness, electronegativity, EA, IP and electrophilicity). Natural population analysis (NPA) and Molecular electrostatic potential (MEP) were also performed to obtain insights about the reactivity of compounds 1–3. Theoretical calculations indicate that these compounds have considerable low reactivity and can be used for development of coordination chemistry under optimum conditions.

Synthesis and Modification of Some New Prodrug Polymers Based on Chitosan and Study of Some Applications

Synthesis of a new various drug delivery systems (DDS) could develop to provide the modifications and improve the therapeutic efficiency and safety of drugs. These may cause a reduction in size and number of doses, side effects, and biological inactivation and elimination. Also, the benefits may include lower toxicity and higher specificity of action This study includes the preparation of new polymers for chitosan by the interaction of chitosan with different drugs carrying carboxylic groups (cephalexin, ciprofloxacin, amoxicillin, mefenamic acid) after conversion into acid chloride derivatives and diagnosis of the resulting compounds using the FT-IR and HNMR spectrum. How to cite this article: Hassen, T.F., Mohammed, F.H. (2019). Synthesis and Modification of Some New Prodrug Polymers Based on Chitosan and Study of Some Applications. International Journal of Drug Delivery Technology, 9(4): 580-586. Source of support: Nil. Conflict of interest: None.

Synthesis of Ethyl 4-(4-Nitrophenoxy) Picolinate

Ethyl 4-(4-nitrophenoxy) picolinate 4 is an important intermediate for the synthesis of many biologically active compounds. The compound ethyl 4-(4-nitrophenoxy) picolinate was obtained by three simple steps to synthesis from 2-picoliniacid. In this paper, three novel chloropicolinoyl chloride derivatives were prepared. The structure was confirmed by MS and 1H NMR. Furthermore, the synthetic method was optimized. The total yield of the target product was 78.57%.

Regiocontrolled palladium-catalyzed direct C2-arylations of Methoxalen using benzenesulfonyl chlorides and C2,C3-diarylations using aryl bromides as the aryl sources

Conditions for the regioselective palladium-catalyzed direct C2-arylation and C2,C3-diarylation of Methoxalen are described. The use of benzenesulfonyl chlorides as the coupling partner allowed control of the regioselectivity of the arylation in favor of the C2 carbon of Methoxalen. This method tolerates a variety of substituents on the benzenesulfonyl chloride derivative. Notably, 2-, 3-, and 4-bromobenzenesulfonyl chlorides and 4-iodobenzenesulfonyl chloride were coupled with Methoxalen without cleavage of the C-Br or C-I bonds. Conversely, the use of an excess amount of aryl bromides as the aryl source provides access to C2,C3-diarlyated Methoxalenes.

Magnetically recoverable MgFe2O4/conjugated polyvinyl chloride derivative nanocomposite with higher visible-light photocatalytic activity for treating Cr(VI)-polluted water

A facile three-step method was adopted to synthesize MgFe2O4/conjugated polyvinyl chloride (CPVC) nanocomposite. XRD, Raman, XPS, SEM, EDX, element mapping, and HRTEM analyses confirmed the formation of MgFe2O4/CPVC nanocomposite. The optical and magnetic properties of the obtained MgFe2O4/CPVC nanocomposite were measured using UV–Vis spectrophotometer and vibrating sample magnetometer, respectively. Through photocatalytic reduction of aqueous Cr(VI) under visible-light (λ > 420 nm) irradiation, it can be noticed that MgFe2O4/CPVC nanocomposite had both improved visible-light photocatalytic activity (about 2.1 times that of MgFe2O4 nanoparticles) and good photocatalytic stability. Moreover, MgFe2O4/CPVC nanocomposite can also be easily recovered by use of a magnet. Based on electrochemical impedance, transient photocurrent response and Mott-Schottky measurement, the mechanism responsible for the enhanced photocatalytic activity of MgFe2O4/CPVC nanocomposite was proposed. Finally, MgFe2O4/CPVC nanocomposite was applied to photocatalytic treatment of the diluted black chromium electroplating solution at different pH. Results showed that MgFe2O4/CPVC nanocomposite had significant visible-light photocatalytic activity in treating the diluted black chromium electroplating solution over a wide pH range (1.4–10.3), and its treatment efficiency increased with the decrease of solution pH. Thus, MgFe2O4/CPVC nanocomposite has the potential to be a new magnetically recoverable, high-performance visible-light photocatalyst for treating Cr(VI)-polluted water.