Synthesis Of Bis Research Articles

Phthalocyanines bearing silazane group for colorectal cancer

The synthesis of bis(trimethylsilyl)amine substituted zinc(II), and indium(III) chloride phthalocyanine complexes have been performed. The obtained compounds were characterized by spectroscopic methods. All synthesized phthalocyanine derivatives were evaluated for cytotoxic, genotoxic, and apoptotic activities on LoVo cell lines which are the standard colorectal cancer cell lines derived from metastatic site: left supraclavicular region. Non-peripheral silazane substituted zinc phthalocyanine (5) showed quite different behavior from all the other compounds analyzed and found to be the best cytotoxic, genotoxic, and apoptotic compound. All derivatives showed no proliferative effect at all doses. All phthalocyanine compounds increased cytotoxicity, DNA damage, apoptosis, and intracellular ROS dose-dependent manner. To explain and verify in vitro tests, phthalocyanine compound structures were optimized using density functional theory, and in silico molecular docking studies on B-DNA dodecamer were performed. Both the experimental and theoretical findings comply with each other.

GO-Fe3O4-Ti(IV) as an efficient magnetic catalyst for the synthesis of bis(indolyl)methanes and benzo[a]xanthen-11-one derivatives

In this study, a new and efficient magnetic composite was synthesized based on graphene oxide (GO). Initially, GO was coated with magnetite, and then Ti(IV ) was fixed on GO-Fe3O4 via a covalent graft. The magnetic composite was characterized by FT-IR, EDS, XRD, FE-SEM, TEM, VSM and TGA techniques. It was designed as a compound with strong and recoverable catalytic properties. The prepared GO-Fe3O4-Ti(IV) emerged to be of high catalytic activity for the synthesis of bis(indolyl)methane and benzo[a]xanthen-11-one derivatives under mild conditions. The stability and reusability of the catalyst were investigated too. All of the data proved that GO-Fe3O4-Ti(IV) could be recycled five times without a marked loss of activity.

Selective Synthesis and Characterization of the Highly Energetic Materials 1-Hydroxy-5H-tetrazole (CHN4 O), its Anion 1-Oxido-5H-tetrazolate (CN4 O- ) and Bis(1-hydroxytetrazol-5-yl)triazene.

For the first time, an adequate selective synthesis, circumventing the formation of 2‐hydroxy‐5H‐tetrazole, of 1‐hydroxy‐5H‐tetrazole (HTO), as well as the synthesis of bis(1‐hydroxytetrazol‐5‐yl)triazene (H3T) are reported. Several salts thereof were synthesized and characterized which resulted in the formation of new primary and secondary explosives containing the 1‐oxidotetrazolate unit. Molecular structures are characterized by single‐crystal X‐ray diffraction, 1H and 13C NMR, IR, and elemental analysis. Calculation of the detonation performance using the explo5 code confirmed the energetic properties of 1‐hydroxy‐5H‐tetrazole. The detonation properties can be adjusted to the requirements for those of a secondary explosive by forming the hydroxylammonium (6) or hydrazinium (7) salts, or to meet the requirements of a primary explosive by forming the silver salt 4, which shows a fast DDT on contact with a flame. The sensitivities of all compounds towards external stimuli such as impact, friction, and electrostatic discharge were measured.

An Update on the Synthesis and Applications of Bis(Naphthoquinones): An Important Class of Molecules against Infectious Diseases and other Conditions.

Naphthoquinones are important molecules belonging to the general class of quinones, and many of these compounds have become drugs that are in the pharmaceutical market for the treatment of several diseases. A special subclass of compounds is that of the bis(naphthoquinones), which have two linked naphthoquinone units. In the last few years, several synthetic approaches toward such valuable compounds have been described, as well as their evaluation against numerous important biological targets. In this review, we provide a thorough discussion on the various synthetic methods reported for the synthesis of bis(naphthoquinone) analogues, also highlighting the biological activities of these substances.

Theoretical–Experimental Study of the Release of Chlorine during the Synthesis of BHET in the Presence of PVC

AbstractThis work studies the chlorine (Cl) release during the esterification of terephthalic acid (TPA) and ethylene glycol (EG) due to the addition of different amounts of polyvinyl chloride (PVC) that emulates its presence as an impurity. With the aim to explore the possible effects of PVC presence and its dehydrochlorination during the syntheses of bis(2‐hydroxyethyl) terephthalate (BHET) and with the aid of a mathematical model, the evolution releasing of Cl during PVC dehydrochlorination is analyzed. Theoretical results present a good correlation with experimental data that indicate the presence of Cl in the composition of the final product because the dehydrochlorination is incomplete. Additionally, the model predicts the temperature in that Cl can be completely released avoiding its presence in BHET. These kinds of studies are of particular interest when products with a high degree of purity are required, and Cl is detrimental to end applications.

Synthesis of Bi2MoO6 and Activating Peroxymonosulfate to Enhance Photocatalytic Activity under Visible Light Irradiation

AbstractBi2MoO6 nanoflakes are synthesized via a normal hydrothermal method. Bi2MoO6 photocatalysts show lower photocatalytic activity for the degradation of methylene blue under visible light irradiation. In order to further enhance the degradation efficiency, Bi2MoO6 is used to activate the peroxymonosulfate for the degradation of methylene blue under visible light. Bi2MoO6 nanoflakes show excellent degradation efficiency in the Bi2MoO6/Vis/peroxymonosulfate (PMS) system. Moreover, the influences of PMS dosage, pH value, and inorganic anions on photodegradation are evaluated. The mechanism of activating peroxymonosulfate is proved by radical quenching experiment, which reveals that sulfate radicals govern the removal of methylene blue.

A Cytotoxic Bis(1,2,3-triazol-5-ylidene)carbazolide Gold(III) Complex Targets DNA by Partial Intercalation.

The syntheses of bis(triazolium)carbazole precursors and their corresponding coinage metal (Au, Ag) complexes are reported. For alkylated triazolium salts, di‐ or tetranuclear complexes with bridging ligands were isolated, while the bis(aryl) analogue afforded a bis(carbene) AuI‐CNC pincer complex suitable for oxidation to the redox‐stable [AuIII(CNC)Cl]+ cation. Although the ligand salt and the [AuIII(CNC)Cl]+ complex were both notably cytotoxic toward the breast cancer cell line MDA‐MB‐231, the AuIII complex was somewhat more selective. Electrophoresis, viscometry, UV‐vis, CD and LD spectroscopy suggest the cytotoxic [AuIII(CNC)Cl]+ complex behaves as a partial DNA intercalator. In silico screening indicated that the [AuIII(CNC)Cl]+ complex can target DNA three‐way junctions with good specificity, several other regular B‐DNA forms, and Z‐DNA. Multiple hydrophobic π‐type interactions involving T and A bases appear to be important for B‐form DNA binding, while phosphate O⋅⋅⋅Au interactions evidently underpin Z‐DNA binding. The CNC ligand effectively stabilizes the AuIII ion, preventing reduction in the presence of glutathione. Both the redox stability and DNA affinity of the hit compound might be key factors underpinning its cytotoxicity in vitro.

Hantzsch synthesis of bis(pyrido[2,3-d:6,5-d']dipyrimidines), bis(pyrimido[4,5-b]quinolines), and bis(benzo[4,5]imidazo[2,1-b]quinazolines) linked to pyrazole units as novel hybrid molecules

Bis(1-phenylpyrazole-4-carboxaldehydes) were utilized as versatile precursors to novel series of bis(pyrido[2,3-d:6,5-d']dipyrimidines), bis(pyrimido[4,5-b]quinolines), and bis(benzo[4,5]imidazo[2,1-b]quinazolines) derivatives which are linked to pyrazole units.

Synthesis of Bi(1,2,3-triazoles) by a Three-Component Reaction

Key words triazoles - rearrangement - multicomponent reaction - azides

Synthesis, Characterization and Antibacterial Evaluation of 2, 3Dihydroquinazolin-4 (1H)-Ones and Some New Bis 2, 3- Dihydroquinazolin-4 (1H)-Ones Using Pre-made Pyrazole Carbaldehyde Derivatives

2, 3-Dihydroquinazolinones are of popular compounds with the diversification of biological and pharmacological activities. Among many discovered methods, there are efficient and convenient methods used for the synthesis of 2, 3-dihydroquinazoline-4 (1H)-one and some new bis 2, 3- dihydroquinazoline-4 (1H)-one derivatives which are reported in this study. The mentioned methods include the two-component condensation of one molecule of anthranilamide and one molecule of pyrazole carbaldehyde using montmorillonite-K10 as a catalyst for the preparation of 2, 3 dihydroquinazoline- 4 (1H)-ones. Also, one-pot pseudo-five-component reaction (5MCRs) of two molecules of isatoic anhydride, two molecules of pyrazole carbaldehydes and one molecule of ethan-1, 2-diamine in the presence of the r catalyst (montmorillonite-K10) for the synthesis of bis 2, 3-dihydroquinazoline-4 (1H)-ones. Despite the short times of reactions, high yields of products were obtained, which were validated using FT-IR, <sup>1</sup>HNMR, <sup>13</sup>CNMR, and elemental analysis. Moreover, the compounds were screened for their antimicrobial activities against two-gram-positive bacterial strains: Staphylococcus aureus and Micrococcus Luteus; and against two-gram-negative bacterial strains, as well: Escherichia coli and Pseudomonas aeruginosa, which all were utilized for antibacterial investigations. The results showed moderate or significant antibacterial activities.

Synthesis of bis(benzoxazole) frameworks chiralized by planar chiral [2.2]Paracyclophane

In this study, a new class of chiral bis(benzoxazole) has been synthesized. The bis(benzoxazole) framework, which has an achiral structure was chiralized by a planar chiral [2.2]paracyclophane moiety. Both enantiomeric forms of the bis(benzoxazole) derivatives were successfully obtained in 99% ee. Even though the starting material was not completely enantiomerically pure, enantiomeric enrichment was afforded by the Horeau principle in the synthesis route.

Solvent-free multi-component synthesis of unsymmetrical bis(indolyl)alkanes with Lewis acid-surfactant-SiO2 as nanocatalyst

Herein we report the multicomponent synthesis of the bis(indolyl)methane derivatives in a ball mill. The reaction was carried out under solvent-free conditions using only the Lewis acid-surfactant-SiO2 composite nanocatalyst (LASSC) prepared in situ. The unsymmetrical bis(indolyl) methane derivatives containing nitro or fluorine substitution with a yield of 72%–92% were obtained in a short reaction time. Within we verified that under the action of the combined catalyst of AlCl3·6H2O + SDS + SiO2, the method of preparing unsymmetrical bis(indolyl)methane by mechanical grinding without solvent has obvious advantages. Finally, we inspected that the catalysis system can be used eight times without a significant decrease in activity.

Expedient Microwave-Assisted Synthesis of Bis(n)-lophine Analogues as Selective Butyrylcholinesterase Inhibitors: Cytotoxicity Evaluation and Molecular Modelling

In the brain of patients with chronic Alzheimer’s disease (AD), the butyrylcholinesterase (BuChE) levels rise while the acetylcholinesterase (AChE) levels decrease. Therefore, development of new selective BuChE inhibitors is of vital importance. Here we present a series of bis(n)‑lophine analogues, where two lophine derivatives are connected by a methylene chain. The bis(n)-lophine analogues were synthesized through one-pot four component reaction between pyridinecarboxaldehydes, 1,n-alkanediamines, benzil, and ammonium acetate. The reactions were performed in a microwave reactor in one step for symmetrical bis(n)-lophines, and in two steps for unsymmetrical bis(n)-lophines. The compounds are strongly selective to BuChE, since none of them inhibit AChE. All the compounds, except 7a, 7b and 7c, displayed potent inhibitory activity against BuChE at a micromolar and sub-micromolar range (half maximal inhibitory concentration (IC50) 32.25-0.03 μM). The enzyme kinetic and docking studies suggests that the inhibitor act as a dual binding site inhibitor, binding into the bottom of the gorge and in the peripheral anionic site (PAS) of BuChE cavity. Furthermore, in vitro studies showed that compounds 5b and 12b had no cytotoxic effects in kidney Vero, hepatic HepG2 and C6 astroglial cell lines.

Synthesis of bis(1,5‐disubstituted tetrazoles) via double four component Azido‐Ugi reaction

AbstractA double four component Azido‐Ugi reaction of isocyanide, TMSN3, aldehyde, and 4,4′‐sulfonyldianiline with two amine functional groups in MeOH at 65°C has been described. The synthesis of pharmacologically and structurally interesting compounds with two 1,5‐disubstituted tetrazole rings via a reaction from available and inexpensive reagents under a convenient process and mild reaction conditions has been reported. Modifications in the structure of the reaction product could be followed by varying the aldehyde or isocyanide component. The products are new and were well described by Mass, 1H NMR, and 13C NMR spectral studies.

Copper(II) and cobalt(II) complexes based on methyl trifluorosalicylate and bipyridine-type ligands: Synthesis and their antimicrobial activity

The synthesis of bis(salicylato)Cu(II) and Co(II) chelates based on methyl trifluorosalicylate and the corresponding M(OAc)2 in the presence of alkali is reported. The following reaction with 2,2′-bipyridine and 1,10-phenanthroline in refluxing methanol affords heteroligand complexes containing methyl trifluorosalicylate and azaheterocyclic ligands in the ratio 2:1. However, the refluxing of Co(II) chelates in ethanol resulted in transesterification of methyl ester group to form heteroligand complexes of ethyl trifluorosalicylate while Cu(II) chelates underwent hydrolysis of ester group to obtain heteroligand complexes of trifluorosalicylic acid. The structures of obtained metal complexes were confirmed by X-Ray diffraction experiment, IR spectroscopy and elemental analysis. The antimycotic and antibacterial activities of synthesized metal complexes were investigated. The heteroligand metal complexes were found to exhibit moderate anti-Candida albicans activity. Among new series of complexes, the most activity showed the mixed metal complexes of trifluorosalicylates and 1,10-phenanthroline revealing a wide range of action in relation to pathogenic fungi and bacteria.

Synthesis of bis[benzyl‐N′‐hydrazinecarbodithioato‐κ2N′,S]nickel(II) complex as a novel lead molecule for cancer treatment

A novel bis[benzyl‐N′‐hydrazinecarbodithioato‐κ2 N′,S]nickel(II) complex was synthesized and characterized by means of various physical, chemical, and spectroscopic techniques. The X‐ray single crystal diffraction analysis indicated two independent close comparable bis‐chelated square planar complexes of trans‐configuration, where S‐benzyl dithiocarbazate (SBDTC) ligand is coordinated via N,S‐donor set. The complex is able to inhibit Ehrlich ascites carcinoma (EAC) cell proliferation by 51.81% and 75.75%, with 0.3 and 50 mg kg−1 (dose adjusted) dose, respectively, administered intraperitoneally for five successive days in mice model. Apoptotic cell morphological changes were examined using optical and fluorescence microscopy techniques. Expression pattern of apoptosis regulatory genes in EAC cells treated with the synthesized nickel(II) complex for five consecutive days showed an increased expression of P53, Bax, Cas‐8, Cas‐9, Cas‐3, Cyt‐c, and TNF‐α proapoptotic genes and decreased expression of antiapoptotic Bcl‐2 gene. The Ni(II) complex and Bleomycin (standard drug) were used in molecular docking coupled with molecular dynamics simulation studies with the aim to support the experimental results and to investigate the apoptotic effect towards the targeting apoptotic genes. Both experimental and computational studies reveal that the nickel(II) complex inhibits EAC cells growth successfully, suggesting a potential compound for cancer treatment.

Convenient Synthesis and Anticancer Activity of Bis(aryl)alkanes and Bis(indolyl)methane Alkaloid Analogs

An efficient metal free high yield method of synthesis of bis(indolyl)methanes (BIMs) and bis(aryl)alkanes analogs in the presence of B(C6F5)3 by condensation of primary amines with pyruvates has been successfully developed. Some analogs of BIMs display good in vitro antitumor activity, screened by MTT assay. Compound 3b demonstrates the best anti-cancer activity against lung carcinoma cell A549 cells with IC50 of 4.52 µM.

Synthesis, structure, photophysical properties and evaluation of in vitro cytotoxic activity of homoleptic dipyrrin based palladium complexes

The synthesis of bis(dipyrrinato)palladium(II) complexes (PD1-PD4) from functionalized dipyrromethanes was achieved via a simple and versatile route involving the oxidation of meso-substituted dipyrromethane followed by complexation with palladium acetate. All the complexes were characterized in detail using various spectroscopic techniques and their structures explicitly confirmed by X-ray crystallography. The crystal structures of the complexes PD1 and PD4 revealed an overall ‘zig-zag’ arrangement for the molecules due to the bent geometry of the meso-substituents with respect to the dipyrrin plane. The photophysical properties were meticulously studied; the complexes exhibit weak luminescence in the blue-green spectral region (λem = 500–575 nm) with lifetime of 2.5–3.8 ns. A short triplet state lifetime of 28.97–67.61 ns was observed for the complexes, as determined by nanosecond transient absorption spectroscopy. All the complexes were tested for their cytotoxicity through a trypan blue-based in vitro assay on DLA cancer cell lines and the results were compared with normal spleen cells. Interestingly, low IC50 values were obtained for PD3 against the cancerous cells, whereas the complexes are inactive towards normal cell lines. The antiproliferative activity revealed the potential of these complexes for further development as in vivo anticancer agents.

“Inorganic Polymer Flocculation Catalyst”—Polyaluminum chloride as highly efficient and green catalyst for the Friedel-crafts alkylation of bis(indolyl)methanes

The classic inorganic polymer flocculant—polyaluminum chloride (PAC)—was used as an environmentally friendly, efficient, and recyclable catalyst in the synthesis of Bis(indolyl)methanes (BIMs) compounds for the first time. The strategy of catalysis is to use PAC as a Lewis acid, which contains different structures of Al–O polynuclear cations. These Al atoms may have a special synergistic catalytic effect for synthesis of BIMs compounds. PAC exhibits excellent catalytic activity in both solution (Yield: 95%) and solid phase (Yield: 99%). In addition, the PAC catalyst possesses outstanding stability and can be reused at least 4 times. Therefore, PAC may have wider applications in the synthesis of other organic compounds.

Copper(II) and Cobalt(II) Complexes Based on Methyl Trifluorosalicylate and Bipyridine-Type Ligands: Synthesis and Their Antimicrobial Activity

The synthesis of bis(salicylato)Cu(II) and Co(II) chelates based on methyl trifluorosalicylate and the corresponding M(OAc) 2 in the presence of alkali is reported. The following reaction with 2,2’-bipyridine and 1,10 phenanthroline in refluxing methanol affords heteroligand complexes containing methyl trifluorosalicylate and azaheterocyclic ligands in the ratio 2:1. However, the refluxing of Co(II) chelates in ethanol resulted in transesterification of methyl ester group to form heteroligand complexes of ethyl trifluorosalicylate while Cu(II) chelates underwent hydrolysis of ester group to obtain heteroligand complexes of trifluorosalicylic acid. The structures of obtained metal complexes were confirmed by X-Ray diffraction experiment, IR spectroscopy and elemental analysis. The antimycotic and antibacterial activities of synthesized metal complexes were investigated. The heteroligand metal complexes were found to exhibit moderate anti-Candida albicans activity. Among new series of complexes, the most activity showed the mixed metal complexes of trifluorosalicylates and 1,10-phenanthroline revealing a wide range of action in relation to pathogenic fungi and bacteria.