Phenyl Sulfonyl Research Articles

Coordination of Thermally Activated Delayed Fluorescent Molecules for Efficient and Stable Perovskite Light‐Emitting Diodes

AbstractThe bandgap and operation stability of metal halide perovskites (MHPs) based light‐emitting diodes (PeLEDs) have been compromised by the substantial surface defect densities in the matrix. Today's defect passivation strategies rely on coordination actions of small‐molecular and/or polymeric ligands, which effectively enhance the optical properties of materials. However, the non‐trivial insulating characteristics of the molecules concurrently sacrifice the operation stability and external quantum efficiency (EQE) of the PeLEDs by augmenting the charge injection barrier at the interface. Herein, a coordinative, charge‐polarized organic semiconductor exhibiting thermally activated delayed fluorescence (TADF), namely 9,9‐dimethyl‐10‐(4‐(phenyl sulfonyl)phenyl)‐9,10‐dihydroacridine (SO‐DMAc) is coordinated, into the MHPs matrix for deep‐red PeLEDs. Owing to the distinctive charge transfer (CT) between the molecule and MHPs with exclusive coordination at the MHP's bottom, SO‐DMAc serves as a molecular bridge that significantly augments the hole injection into the PeLEDs. Encouraged by these improvements, efficient and stable deep red PeLEDs offering EQE of 21.8% and respective half lifetimes (T50) of luminance and EQE exceeding 6 and 35 h are demonstrated. It is revealed that the molecular coordination to the MHP surface is pivotal to manifesting the interfacial CT process for favorable energy level tuning.

Synthesis, crystal structures, spectroscopic characterization and in vitro evaluation of the 4-sulfono-3-methoxycinnamaldehydes as potential α-glucosidase and/or α-amylase inhibitors

The 4-sulfono-3-methoxycinnamaldehyde derivatives 2a–e were synthesized by sulfonation of 4-hydroxy-3-methoxycinnamaldehyde 1 with alkyl or phenyl sulfonyl chlorides. Both single crystal X-ray diffraction (XRD) and 1H NMR spectroscopic techniques provided proof of the trans stereochemistry of the α,β-unsaturated carbonyl arm of these molecular constructs. XRD method confirmed the trans isomer to exist exclusively in the solid state. NOESY experiment, on the other hand, confirmed the presence in the solution phase of also a conformer with cis alkenyl moiety and a trans orientation of the aldehyde group. This observation was corroborated by density functional theory studies which predicted the coexistence of both cis and trans isomers in the gas phase. The Hirshfeld surface and 2D fingerprint plots were used to understand the intermolecular interactions responsible for the molecular packing in the crystal lattices of these compounds. Their potential to inhibit α-glucosidase and/or α-amylase activities were evaluated through enzymatic assays in vitro complemented with molecular docking studies. 4-(Methoxyphenyl)sulfono-3-methoxycinnamaldehyde (2d) exhibited increased inhibitory effect against α-glucosidase (IC50 = 0.68 ± 1.36 µM) and α-amylase (IC50 = 22.99 ± 0.45 µM) compared to substrate 1 (IC50 = 1.70 ± 1.77 µM & 30.45 ± 0.30 µM, respectively) and acarbose (IC50 = 4.46 ± 1.52 µM & 25.48 ± 0.80 µM, respectively). The experimental results were complemented with data from molecular docking of the most active derivatives and molecular dynamics simulation study of derivatives with highest binding energies against α-glucosidase and α-amylase.

Synthesis and herbicidal activity of novel 1,2,4-triazole derivatives containing fluorine, phenyl sulfonyl and pyrimidine moieties

In this study, 4-amino-2-(alkylthio)-6-(methylthio) pyrimidine-5-carbonitrile Ι were employed as the starting materials to synthesize a novel series of 1,2,4-triazole derivatives containing fluorine, phenyl sulfonyl and pyrimidine moieties Ⅳ-1∼Ⅳ-39. The preliminary bioassay indicated that many newly synthesized compounds exhibited moderate to good herbicidal activities against the monocotyledons (Echinochloa crusgalli, Sorghum bicolor) and dicotyledons (Raphanus sativus, Brassica campestris, Cucumis sativus, and Medicago sativa) at the concentrations of 100 mg·L−1 and 10 mg·L−1. Especially, compound (Ⅳ-8) displayed good herbicidal activity, with 100% inhibition against Brassica campestris, Cucumis sativus, and Medicago sativa at a concentration of 100 mg·L−1.

Potent biological investigation into a new class of sulfone derivatives endowed with quinolinyl–cyclopropane analogue

Novel series of quinoline derivatives incorporating cyclopropyl ring and sulfone linkage as substituents have been synthesized, and oxidation of ethyl-2-cyclopropyl-4-(substituted phenylthio)quinoline-3-carboxylate was carried out to set ethyl-2-cyclopropyl-4-(substituted phenyl sulfonyl)quinoline-3-carboxylate. An ecofriendly synthesis of sulfone derivatives was carried out by the reaction of glacial acetic acid and 30% hydrogen peroxide at room temperature. The synthesized quinoline incorporating sulfone linkage derivatives was evaluated for their anticipated antimicrobial activity as well as characterized by their melting point, mass spectra, IR, 1H NMR and 13C NMR spectra. For proving the structural biological activity, herein we have carried out SAR and HOMO–LUMO studies. From these studies, we have found some best results as their energy gap is very low which makes their activity higher, i.e. compounds 11a, 11b, 11h, 11k and 11m.Graphical abstract

Multicomponent Synthesis of Pyrano (3, 2-c) Quinolone Fused Spirochromenes

A multicomponent pathway has been described for the synthesis of novel pyrano (3,2-c) quinolone fused spirochromenes by piperidine catalyzed reaction between isatins, phenyl (or alkyl) sulfonyl acetonitrile and 4-hydroxy-N-methylquinoline-2-one. Decent yields coupled with easy isolation of the products and avoidance of conventional purification methods are the noteworthy merits of the developed protocol.

Synthesis and herbicidal activity of pyrimidyl‐1,2,4‐triazole derivatives containing aryl sulfonyl moiety

AbstractTo discover novel heterocyclic compounds with high herbicidal activity, a series of new pyrimidyl‐1,2,4‐triazole derivatives (Ι‐1 to Ι‐41) was designed and synthesized by incorporating the activating 1,2,4‐triazole, pyrimidine, and phenyl sulfonyl structural templets. Their structures were clearly identified by proton nuclear magnetic resonance (1H NMR), carbon‐13 nuclear magnetic resonance (13C NMR), high‐resolution mass spectroscopy (HRMS), and X‐ray single‐crystal diffraction (compound Ι‐3). Their herbicidal activities against monocotyledons (Echinochloa crusgalli, Sorghum bicolor) and dicotyledons (Raphanus sativus, Brassica campestris, Cucumis sativus, and Medicago sativa) were evaluated using a Petri dish culture method. The results indicated that most of title compounds exhibited significant herbicidal potencies against the plant growth at 100 mg·L−1, while some of them, such as Ι‐2 and Ι‐4, showed remarkable inhibitory effects on weed control at 10 mg·L−1 and 100 mg·L−1. On the whole, compound Ι‐3, which was found to possess an even broader spectrum of inhibitory activities against the roots and stalks of Echinochloa crusgalli, Raphanus sativus, Brassica campestris, Cucumis sativus, and Medicago sativa at 10 and 100 mg·L−1 than that of the commercial herbicide Flumetsulam, could be employed as a new lead structure for further optimization to find more potent herbicides.

New lactam-containing benzenesulfonamides: design, synthesis, and in silico and in vitro studies

A virtual set of new lactam-containing derivatives of arylsulfonylglycines 1a–d and 2a–d was designed and analyzed using structure–activity computer models (web-services PASS Online, AntiBac-Pred, and GUSAR Acutetoxicity). The antimicrobial activity against Staphylococcus aureus along with low toxicity was predicted for these derivatives. Compounds 1a–d and 2a–d were synthesized by the reactions of N-trimethylsilyl lactams with 4-substituted [(phenyl)sulfonyl]aminoacetyl chlorides. The structures of new compounds were confirmed by IR spectroscopy, NMR spectroscopy, and elemental analysis data. According to the results of studies in vitro, compounds 1a–d and 2a–d efficiently suppress the growth of S. aureus. Lactam-containing benzenesulfonamides bearing the bromine atom or methyl or nitro group at position 4 manifested the most pronounced activity.

In Vitro and In Vivo Evaluation of an Adamantyl-Based Phenyl Sulfonyl Acetamide against Cutaneous Leishmaniasis Models of Leishmania amazonensis.

Phenotypic assay against Leishmania amazonensisin vitro and in vivo led to identification of an adamantyl-based phenyl sulfonyl acetamide (compound 1) as a promising antileishmanial agent. Compound 1 inhibited the growth of intracellular forms of L. amazonensis (50% inhibitory concentration [IC50] = 4 μM) and exhibited low toxicity to host cells, with a selectivity index (SI) of >125. However, in a cutaneous leishmaniasis (CL) mouse model, compound 1 did not reduce lesions and parasite load when administered as monotherapy or when given simultaneously with a suboptimal dose of miltefosine.

Drug Re-purposing from SARS-CoV Led the Identification of Potential Candidate Drug Target and Alternate Drug Molecules Against SARSCoV- 2

Background: SARS-CoV-2 causes COVID19 disease where there are no suitable drugs available. Objective: The objective of the work is to repurpose the drugs prescribed for SARS-CoV as the drugs for the control of SARS-CoV-2. Methods:: In this work, we have used homology searches and docking methods for understanding the mechanism of the drugs prescribed for the control of SARS-CoV on SARS-CoV-2. Results: In our analysis, we found that the drugs Benzyl (2-Oxopropyl)carbamate, 2-[(2,4-Dichloro- 5-methyl phenyl)sulfonyl]-1,3-dinitro-5-(trifluoromethyl)benzene, S-[5-(Trifluoromethyl)-4H-1,2,4- triazol-3-YL] 5-(phenylethynyl)furan-2-carbothioate, 4-(Dimethylamino)benzoic acid, which are capable of inhibition of the activity of 3CLPro and prevent the progression of SARS-CoV. Conclusion: In this letter, we describe the findings of the protein ligand interactions between 3CLPro of SARS-CoV, SARS-CoV-2 with Benzyl (2-oxopropyl) carbamate.

Molecular simulation of the separation of toluene and p-xylene with the thermally-robust ionic liquid triphenyl-p-phenyl sulfonyl phenyl phosphonium

Here, we use molecular dynamics simulations to evaluate the behavior of toluene (TOL) and p-xylene (XYL) within three different solvents: n-hexane (HEX), n-heptane (HEP), and a thermally-robust ionic liquid (triphenyl-p-phenyl sulfonyl phenyl phosphonium + bis(trifluoromethylsulfonyl)imide (TPSP + Tf2N)). Several different temperatures are explored, while the solvation structures, energetics, and dynamics of TOL and XYL are evaluated. The solvation free energy (ΔGsolv) and transfer free energy (ΔGtransfer) of TOL and XYL are calculated using thermodynamic integration (TI). The transfer free energy of XYL from HEP/HEX to TPSP + Tf2N is more favorable than that of TOL over the entire temperature range, while the transfer of both TOL and XYL becomes less favorable as the temperature increases. The diffusion rates of TOL and XYL are lower in the ionic liquid when compared to HEP and HEX, but the thermal stability of TPSP + Tf2N may allow for higher operating temperatures and accelerated mass transport rates.

Sodium L-ascorbate-catalyzed one-pot green synthesis of sulfonyl substituted 2-amino-4H-pyran derivatives

In the present research, multicomponent one-pot green synthesis of sulfonyl-substituted 2-amino-4H-pyran derivatives through the reaction of aromatic aldehyde, cyclic ketone and phenyl (or methyl) sulfonyl acetonitrile was developed. This multicomponent reaction distinguishes by employing a less expensive and non-toxic sodium L-ascorbate as a catalyst which represents a simple, efficient and environmentally benign route to obtain sulfonyl substituted 2-amino-4H-pyran derivatives in moderate to good yields. The major advantages of the present work are high efficiency, short reaction time, use of cheap, safe and stable catalyst system as well as green solvent and mild reaction condition. Herein, we introduce an efficient and green multicomponent one-pot protocol for the synthesis of sulfonyl-substituted 2-amino-4H-pyran derivatives in 80% EtOH using sodium L-ascorbate (NaAsc) as catalyst.

Photochemical Strain-Release-Driven Cyclobutylation of C(sp3 )-Centered Radicals.

A new photoredox-catalyzed decarboxylative radical addition approach to functionalized cyclobutanes is described. The reaction involves an unprecedented formal Giese-type addition of C(sp3 )-centered radicals to highly strained bicyclo[1.1.0]butanes. The mild photoredox conditions, which make use of a readily available and bench stable phenyl sulfonyl bicyclo[1.1.0]butane, proved to be amenable to a diverse range of α-amino and α-oxy carboxylic acids, providing a concise route to 1,3-disubstituted cyclobutanes. Furthermore, kinetic studies and DFT calculations unveiled mechanistic details on bicyclo[1.1.0]butane reactivity relative to the corresponding olefin system.

Photochemical Strain‐Release‐Driven Cyclobutylation of C(sp3)‐Centered Radicals

AbstractA new photoredox‐catalyzed decarboxylative radical addition approach to functionalized cyclobutanes is described. The reaction involves an unprecedented formal Giese‐type addition of C(sp3)‐centered radicals to highly strained bicyclo[1.1.0]butanes. The mild photoredox conditions, which make use of a readily available and bench stable phenyl sulfonyl bicyclo[1.1.0]butane, proved to be amenable to a diverse range of α‐amino and α‐oxy carboxylic acids, providing a concise route to 1,3‐disubstituted cyclobutanes. Furthermore, kinetic studies and DFT calculations unveiled mechanistic details on bicyclo[1.1.0]butane reactivity relative to the corresponding olefin system.

A phenoxazine-based fluorescent chemosensor for dual channel detection of Cd2+ and CN− ions and its application to bio-imaging in live cells and zebrafish

A simple phenoxazine-based fluorescence chemosensor N-(4-((4-((5-oxo-5H-benzo [a]phenoxazin-6-yl)amino)phenyl)sulfonyl)phenyl)furan-2-carboxamide (NPC) was developed for discriminative detection of Cd2+ and CN− ions. This easily available chemosensor was synthesized by adding a furan-2-carboxamide group to a phenoxazine fluorophore and a phenyl sulfonyl chelating site. The sensor NPC exhibited turn-on fluorescence emission for Cd2+, and the obtained NPC–Cd2+ complex detected CN−via turn-off fluorescence response with 2:1 binding stoichiometry in CH3CN/H2O (99:1 v/v) medium by fluorescence spectroscopy. The detection limits of Cd2+ and CN− were 0.60 μM and 0.145 μM, respectively, which were significantly lower than the World Health Organization guidelines. The proposed mechanism of sensor NPC was additionally supported by NMR, FT-IR analyses, DFT and a UV/visible titration studies. Furthermore, the sensor NPC has been successfully demonstrated as a biomarker for detecting Cd2+ in live cells and zebrafish larvae.

8-(METHYL(PHENYL)SULFONYL)-2,6-DIHYDROIMIDAZO[1,2- c ]-PYRIMIDIN-5(3 Н )-ONES AND 9-(METHYL(PHENYL)SULFONYL)-2,3,4,7-DIHYDRO-6 H -PYRIMIDO[1,6- a ]PYRIMIDIN-6-ONES: SYNTHESIS AND ANTIVIRAL ACTIVITY

A convenient method for the synthesis of novel sulfonic cytosine derivatives, 8-(methyl(phenyl)sulfonyl)-2,6-dihydroimidazo[1,2-c]-pyrimidin-5(3Н)-ones and 9-(methyl(phenyl)sulfonyl)-2,3,4,7-tetrahydro-6H-pyrimido[1,6-a]pyrimidin-6-ones, has been developed based on the reaction of 3-amino-2-(methyl(phenyl)sulfonyl)acrylonitriles with 2-chloroethyl isocyanate and 3-chloropropyl isocyanate. The resulting heteryl sulfones possess antiviral activity.

8-(Methyl(phenyl)sulfonyl)-2,6-dihydroimidazo[1,2-c]- pyrimidin-5(3Н)-ones and 9-(methyl(phenyl)sulfonyl)- 2,3,4,7-dihydro-6H-pyrimido[1,6-a]pyrimidin-6-ones: synthesis and antiviral activity

A convenient method for the synthesis of novel sulfonic cytosine derivatives, 8-(methyl(phenyl)sulfonyl)-2,6-dihydroimidazo[1,2-c]-pyrimidin-5(3Н)-ones and 9-(methyl(phenyl)sulfonyl)-2,3,4,7-tetrahydro-6H-pyrimido[1,6-a]pyrimidin-6-ones, has been developed based on the reaction of 3-amino-2-(methyl(phenyl)sulfonyl)acrylonitriles with 2-chloroethyl isocyanate and 3-chloropropyl isocyanate. The resulting heteryl sulfones possess antiviral activity.

Multicenter Polyester Initiators for the Preparation of Graft Copolymers with Oligo(2‐Oxazoline) Side Chains

Multicenter polyester initiators intended for the cationic polymerization of oxazolines were synthesized via high‐temperature polycondensation of 2‐(4‐(2‐bromoethyl)phenyl sulfonyl hydroquinone with a number of aromatic and alkylene‐aromatic dichloroanhydrides. The Kuhn segment values, liquid‐crystalline properties, and molecular‐mass characteristics of the macroinitiators are determined. The synthesized macroinitiators were used in cationic ring‐opening polymerization to obtain hybrid comb polymers containing poly(2‐oxazoline) side chains. It was suggested the method for estimating the length of poly(oxazoline) side fragments and graft density. It was demonstrated that at a certain ratio between backbone length and side chain length (which depends on chemical structure of the initiator), comb copolymers The graft copolymers form aqueous micellar solutions with a narrow particle‐size distribution. They possess a lower critical solution temperature.

Synthesis of Some Substituted 6-Phenyl Purine Analogues and Their Biological Evaluation as Cytotoxic Agents.

A series of 6-(4-substituted phenyl)-9-(tetrahydropyran-2-yl)purines 3-9, 6-(4-substituted phenyl)purines 10-16, 9-((4-substituted phenyl)sulfonyl)-6-(4-substituted phenyl)purines 17-32 were prepared and screened initially for their in vitro anticancer activity against selected human cancer cells (liver Huh7, colon HCT116, breast MCF7). 6-(4-Phenoxyphenyl) purine analogues 9, 16, 30-32, had potent cytotoxic activities. The most active purine derivatives 5-9, 14, 16, 18, 28-32 were further screened for their cytotoxic activity in hepatocellular cancer cells. 6-(4-Phenoxyphenyl)-9-(tetrahydropyran-2-yl)-9H-purine (9) had better cytotoxic activity (IC50 5.4 μM) than the well-known nucleobase analogue 5-FU and known nucleoside drug fludarabine on Huh7 cells. The structure-activity relationship studies reported that the substitution at C-6 positions in purine nucleus with the 4-phenoxyphenyl group is responsible for the anti-cancer activity.

The effect of structural modifications on the thermal stability, melting points and ion interactions for a series of tetraaryl-phosphonium-based mesothermal ionic liquids.

A family of mesothermal ionic liquids comprised of tetraarylphosphonium cations and the bis(trifluoromethanesulfonyl)amidate anion are shown to be materials of exceptional thermal stability, enduring (without decomposition) heating in air at 300 °C for three months. It is further established that three specific structural elements - phenoxy, phenacyl, and phenyl sulfonyl - can be present in the cation structures without compromising their thermal stability, and that their incorporation has specific impacts on the melting points of the salts. Most importantly, it is shown that the ability of such a structural component to lower a salt melting point is tied to its ability to lower cation-cation repulsions in the material.

STUDY OF BINDING INTERACTIONS OF HUMAN CARBONIC ANHYDRASE XII

Objective: The present study was carried out to study the binding interactions of different N’-(substituted phenyl sulfonyl)-pyridine-2-carbohydrazide derivatives and N’-(substituted phenyl sulfonyl)-thiophene-2-carbohydrazide derivatives which were synthesized by senior students from research laboratory, with objective to explore the suitability of selected ligands for their binding affinity for the selected target.Methods: Binding interactions of the selected ligands were studied using glide module of Schrodinger software using Maestro 10.1 interface. At the end of molecular docking studies, docking scores along with 2D and 3D binding interactions of these ligands were studied to evaluate the potency of ligands to act as selective human carbonic anhydrase (hCAXII) inhibitors in comparison with standard inhibitor Acetazolamide (AZA).Results: Docking study on the ligands exhibited very similar conformation and binding interactions with hCAXII as that of standard. This suggests that selected ligands might possess significant binding affinity for hCAXII.Conclusion: It can be concluded that the selected ligands have the potential to act as inhibitors of hCAXII.