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• A novel series of triazole, sulfonamide and sulfonyl urea derivatives of N -acylhomoserine lactones (HSL) have been prepared. • These novel molecules were screened against Chromobacterium violaceum ATCC 12472 for their quorum sensing inhibitory (QSI) activity. • Among them, compounds 6, 7 and 14 showed comparable antibacterial activities with reference to penicillin and streptomycin as 37.5 µg/mL, while compounds 7, 13 and 17 exhibited promising QSI activity. Triazole, sulfonamide and sulfonyl urea derivatives of N -acylhomoserine lactones (AHLs) have been prepared from homoserine lactone hydrobromide which in turn is derived from l -methionine. The molecules were screened against Chromobacterium violaceum ATCC 12472 for their quorum sensing inhibitory (QSI) activity. Among them, compounds 6, 7 and 14 were exhibited comparable antibacterial activities with reference to penicillin and streptomycin as 37.5 µg/mL, while compounds 7, 13 and 17 exhibited promising QSI activity. These compounds represent a synthetically accessible class of AHL analogs could find utility to improve their potency. [Display omitted] [ABSTRACT FROM AUTHOR]

A new sulfonamide-derived prophane sulfonyl hydrazone compounds: 2-hydroxy- acetophenoneprophanesulfonylhydrazone (afpsh) , 5-Cl-2-hydroxyacetophenoneprophane sulfonylhydrazone (5-Clafpsh) , 3,5-di-tert-butyl-2-hydroxybenzaldehydeprophanesulfonyl hydrazone (3,5tbsalpsh) and their Pd(II) complexes were synthesized. The characterization of all compounds was characterized by 1H NMR, 13C NMR, FT-IR, Mass spectral data, elemental analysis and magnetic susceptibility measurements. The crystal structure of afpsh was determined by single crystal X-ray diffraction methods. 1H and 13C shielding tensors of afpsh were calculated with GIAO/DFT/B3LYP/6–311++G(d,p) methods in DMSO. Molecular electrostatic potential surface and frontier orbital analysis were also carried out. HOMO-LUMO energy gap was calculated which allowed the calculation of relative reactivity descriptors like chemical hardness, chemical inertness, chemical potential, nucleophilicity and electrophilicity index of all compounds. It has been observed that the calculated band gaps for Pd (II) complexes are much smaller than ligands. The microbiological effect of ligands and Pd(II) complexes were tested against six human pathogenic bacteria (three Gram-positive and three Gram-negative strains) by using microdilution (as MICs) and disc diffusion (as mm zone) methods. It was found that all compounds, in particular Pd (II) complexes, were more active than sulfonyl hydrazones. Image 1 • Novel Pd(II) complexes with sulfonyl hydrazones were synthesized. • Single crystal X-ray studies revealed the structure of the afpsh. • The minimum inhibitory concentration of the sulfony hdrazone and Pd(II) complexes against bacterial strains was determined. • The Pd(II) compexes of sulfonyl hydrazone emerged as good bacterial inhibitors. • Bioactivity studies show that the Pd(II) complex can interact with in vitro. [ABSTRACT FROM AUTHOR]

[Display omitted] The reactions of N -(benz[ d ]oxazol-2-yl)- or N -(benzo[ d ]-thiazol-2-yl)-substituted carbothioamides with sulfonyl azides proceed as replacement of thioxo substituent by the sulfonylimino group to afford the corresponding N' -sulfonylated amidines. Acetic acid thioamides react smoothly upon boiling in ethanol, while for thioamides of trifluoroacetic and benzoic acids heating to 80–90 °C was required. Among hybrid molecules thus prepared, bacteriostatic-, bactericidal- and fungistatic-active against S. aureus and C. albicans representatives were found. [ABSTRACT FROM AUTHOR]

Graphical abstract Highlights • Cu-catalyzed aerobic oxidative coupling of sulfonyl hydrazides and amines was achieved. • Aliphatic sulfonyl hydrazides underwent the present oxidative coupling efficiently. • The developed coupling was effective on a larger scale. • The plausible mechanism was proposed on the basis of several control experiments. Abstract An environmentally friendly route for sulfonamides has been developed. The oxidative coupling of sulfonyl hydrazides and amines was catalyzed by CuBr 2 to produce various sulfonamides with the water and nitrogen gas as byproducts. Preliminary experiments revealed that the sulfonyl radical is likely to be involved in the reaction mechanism. [ABSTRACT FROM AUTHOR]

Graphical abstract Highlights • Three-component reaction of aryl diazonium salt with sulfonamide and acetonitrile. • Nitrilium ion intermediate generates in reaction of aryldiazonium salt with nitrile. • Trapping nitrilium ion by sulfonamide to give N -sulfonyl amidine. • Trapping nitrilium ion by indole to give indolyl imine. Abstract A new method was developed to prepare N -sulfonyl amidine compounds through three-component reaction of aryl diazonium salts with sulfonamides and acetonitrile, in which, nitrilium ion intermediate, generated from the reaction of aryldiazonium salt with nitrile, was subsequently trapped by sulfonamides. A series of N -sulfonyl amidine derivatives were synthesized by using various types of aryl diazonium salts, sulfonamides and nitriles. In addition, indolyl imine products could also be prepared by using indole as the nucleophile to trap nitrilium ion intermediate. [ABSTRACT FROM AUTHOR]

A novel, rapid, and environmentally-friendly protocol for the synthesis of sulfonamides using iodine as catalyst under solvent-free conditions is described. This method involves the oxidative coupling of sulfonyl hydrazides and amines in the presence of catalytic amount of iodine using TBHP as oxidant. This protocol does not require purification techniques such as column chromatography and recrystalization. [ABSTRACT FROM AUTHOR]

[Display omitted] Among all biologically active sulfonamides, primary sulfonamides possessing terminal SO 2 NH 2 group occupy special place due to their high zinc binding capability which has been successfully exploited for discovery of several different medicinally active primary sulfonamides. However, majority of the primary sulfonamide synthesis involve traditional method of treating ammonia with sulfonyl chloride, which in turn is typically obtained either from thiols by harsh oxidation conditions or chlorination of sulfonic acids. We herein report a simple and convenient protocol to access primary sulfonamides by direct sulfonylamidation of unfunctionalized arenes [direct C H activation to C-SO 2 NH 2 ]. Usefulness of the protocol has been further demonstrated successfully by extending the application to formal syntheses of known drugs, acetazolamide (2), methazolamide (3), ethoxzolamide (4), and a pharmacologically active benzolamide (6). [ABSTRACT FROM AUTHOR]

Abstract: An inibition study of the β-carbonic anhydrase (CA, EC 4.2.1.1) DmBCA from the insect Drosophila melanogaster with sulfonamides and sulfamates is reported. Among the panel of 40 investigated compounds, the best DmBCA inhibitors were the sulfonylated benzenesulfonamides and ethoxzolamide, which showed inhibition constants in the range of 65.3–138nM. Methazolamide and sulthiame were also effective inhibitors with K Is ranging between 237 and 249nM, whereas most of the simple aromatic/heterocyclic sulfonamides showed inhibition constants in the range of 0.47–6.40μM. Topiramate, zonisamide and saccharine did not inhibit DmBCA. As orthologs of this mitochondrial CA are found in many insect species involved in the spread of various diseases, inhibitors interfering with their activity may be of interest for developing insecticides with an alternative mechanism of action to the presently used agents, for which many insects developed extensive resistance. [Copyright &y& Elsevier]

• The sulfonamide bearing thiadiazole derivatives were synthesized as enzyme inhibitors. • Target compounds bind strongly with the target enzyme (PDBID 1V9E). • The compounds show anticancer activity through carbonic anhydrase inhibition rather than by DNA binding. A series of sulfonamide derivatives bearing 2,5-disubstituted-1,3,4-thiadiazole (5a–j) have been synthesized. Thiosemicarbazide was reacted with CS 2 to get 2-amino-5-mercapto-1,3,4-thiadiazole 1. The intermediate thiadiazole (1) was alkylated by reacting with different halides (2a–c) to afford the alkylated thiadiazoles (3a–c). The title sulfonamide bearing derivatives (5a–j) have been prepared by condensation of sulfonyl chlorides (4a–d) with thiadiazole derivatives (3a–c). The molecular docking studies of target molecules showed strong binding of compounds (5a–j) with target enzyme (PDBID 1V9E) particularly for compound 5f containing fluoro and methoxy groups. The carbonic anhydrase (CA) inhibitory activity showed derivative 5h to be the most potent (IC 50 0.60 ± 0.02 µM) as compared to acetazolamide (IC 50 0.984 ± 0.12 µM) used as standard. Free radical scavenging activity was measured using ascorbic acid as a reference. It was observed that just like CA inhibition the compound 5h showed greater free radical scavenging activity than all other target molecules. Enzyme inhibition kinetics (Lineweaver-Burk plots) showed a compound (5h) to inhibit the enzyme by mixed type of inhibition (Ki and Kiʹ values 2.91 µM and 3.88 µM, respectively). Compound 5h was further investigated that a smaller value of Ki than Ki ′ showed preferred competitive binding over non-competitive manners. The anticancer activity performed against the MCF-7 cell line showed that the compound 5h inhibits 40% cell growth at 125 µM concentration. The mechanism of anticancer potential was further investigated by DNA binding studies through electrochemical methods. The UV-Vis spectroscopy and Cyclic voltammetry results suggested that 5h was weakly bound to DNA (binding constant 30–32 M−1). It is thus proposed that anticancer activity of 5h may be through carbonic anhydrase inhibition rather than by DNA binding. Our investigations suggested the derivative 5h to serve as a lead structure in designing potentially more active carbonic anhydrase inhibitors. [Display omitted] [ABSTRACT FROM AUTHOR]

Abstract: Benzenesulfonicacid-1-methylhydrazide (1) and its four aromatic sulfonyl hydrazone derivatives (1a–1d), N-(3-amino-2-hydroxypropyl)benzene sulfonamide (2) and N-(2-hydroxyethyl)benzenesulfonamide (3) were synthesized and their structures were determined by IR, 1H NMR, 13C NMR, and LCMS techniques. Antibacterial activities of new synthesized compounds were evaluated against various bacteria strains by microdilution and disk diffusion methods. The experimental results show that presence of OH group on sulfonamides reduces the antimicrobial activity, and antimicrobial activities of the sulfonyl hydrazones (1a–1d) are smaller than that of the parent sulfonamide (1), except Candida albicans. In addition, 2D-QSAR analysis was performed on 28 aromatic sulfonyl hydrazones as antimicrobial agents against Escherichia coli and Staphylococcus aureus. In the QSAR models, the most important descriptor is total point-charge component of the molecular dipole for E. coli, and partial negative surface area (PNSA-1) for S. aureus. [Copyright &y& Elsevier]

• The structure of compound 1 was determined through single crystal X-Ray diffraction. • In-Vitro enzyme inhibition potential were checked in order to explore their biological importance. • DFT and Docking studies were used to compare experimental and theoretical parameters. This study describes the synthesis of four (1-4) new phenylalanine based sulfonamides from benzene sulfonyl chlorides. The progress of the reaction was monitored on TLC and after completion; the products were subjected to various analyses that indicated the synthesis of the targeted molecules. The structure of sulfonamide 1 was elucidated on the basis of Single Crystal X-Ray Diffraction technique. While other sulfonamides were characterized with FTIR spectroscopy. The sulfonamide (1-4) were subjected to Density Functional Theory for optimization of the structures and to calculate the bond angle and bond length of the crystalline molecule (1). The DFT and SCXRD results are in close agreement with each other. All compounds were subjected to radical scavenging and enzyme inhibition studies. The compound 1 exhibited moderate antioxidant activity (38.04 %). Enzyme inhibition potential was checked against three enzymes; trypsin, acetylcholine esterase and butyrylcholine esterase using in-vitro models. This study indicated that 2-(4-acetamidophenylsulfonamido)-3-phenylpropanoic acid (1) was found most active among all the synthetic molecules. It exhibited inhibition of 54.07%, 72.42and 57.18 % against AChE, BChE and trypsin respectively. Docking studies of the four sulfonamides were also done with Molecular Operating Environment, which depicted good docking scores. In-silico studies also suggested good enzyme inhibition potential of these understudied molecules. [Display omitted] [ABSTRACT FROM AUTHOR]

B 2 Pin 2 -assisted copper-catalyzed transfer hydrogenation of aromatic sulfonylimines has been achieved, delivering a variety of aryl/heteroaryl sulfonamides in good to excellent yields under mild reaction conditions and with methanol as the hydrogen source. Mechanistic studies suggest that the reaction may proceed via a transient α-borylated intermediate, followed by protodeboration to afford the sulfonamide products. [Display omitted] • Copper-mediated catalysis. • Transfer hydrogenation. • Aryl sulfonamides. • Heteroaryl sulfonamides. [ABSTRACT FROM AUTHOR]

• Ni(II)-mediated ortho C(sp2)-H bond functionalization of aromatic amide. • Sulfonyl azides as amine source. • (quinolin-8-yl) amine (AQ-amine) as the directing group. In this paper, Ni(II)- Catalyzed ortho-amidation of C(sp2)-H bond with sulfonyl azides directed by (quinolin-8-yl) amine (AQ-amine) is described. The method provides a straightforward method for the synthesis of sulfonamides from available sulfonyl azides via the transition-metal-catalyzed C(sp2)-N bond forming reaction. The amidation reactions exhibit high functional group compatibility, which might proceed a Ni(III)/Ni(I) catalytic cycle. We also applied sulfonamide compound in OLEDs, which exhibits the certain application potential in OLEDs field. [ABSTRACT FROM AUTHOR]

Phosphodiesterase 4 (PDE4) inhibitors have emerged as a new strategy to treat asthma and other lung inflammatory diseases. Searching for new PDE4 inhibitors, we previously reported the discover of LASSBio-448, a sulfonamide with potential to prevent and reverse pivotal pathological features of asthma. In this paper, two novel series of sulfonamide (6a-6m) and sulfonyl hydrazone (7a-7j) analogues of LASSBio-448 have been synthetized and evaluated for selective inhibitory activity toward cAMP-specific PDE4 isoforms. From these studies, we have identified 7j (LASSBio-1632) as a new anti-asthmatic lead-candidate associated with selective inhibition of PDE4A and PDE4D isoenzymes and blockade of airway hyper-reactivity (AHR) and TNF-α production in the lung tissue. In addition, it was able to relax guinea pig trachea on non-sensitized and sensitized animals and showed great TGI permeability. Image 1 • A new selective PDE4A and PDE4D inhibitor. • Good drug-like properties. • Blockade of airway hyper-reactivity (AHR) and TNF-α production in the lung tissue. • relaxant effects on guinea pig trachea. [ABSTRACT FROM AUTHOR]

Charge transfer complex (CTC) formed between (S, S)-bis-N, N-sulfonyl bis- l -phenylalanine dimethylester as donor and 2,3-dichloro-5,6-dicyano- p -benzoquinone (DDQ) as acceptor, has been studied spectrophotometrically. Benesi-Hildebrand and molar ratio methods were applied in order to determine association constant (K CT), molar extinction coefficient (ε CT) and stoichiometric ratio, respectively. The solid CT complex has been synthesized and its structure was characterized via spectroscopic techniques (UV–vis and FT-IR). In order to determine the equilibrium geometries, DFT/CAM-B3LYP has been employed. Moreover, TD-DFT method was used to investigate the electronic structures of donor, acceptor and their complex. Natural bond orbital (NBO) analysis has been used to study the atomic charges and molecular bonding interactions of the interesting complex. These studies show that non-bonding interactions are important in charge transfer complex. • The new CTC complex formed between (S, S)-bis-N, N-sulfonyl bis-L-phenylalanine dimethylester and DDQ was synthesized. • The Benesi-Hildebrand equation was used to calculate the association constant (K). • The CTC was theoretically investigated using DFT: CAM/B3LYP and TD-DFT methods. • The NBO analysis provides a qualitative picture of the Charge-Transfer process. [ABSTRACT FROM AUTHOR]

• A novel strategy for the α-sulfonamidation of cyclic β-ketoesters is described. • This is the first report on metal catalyzed α-sulfonamidation by sulfonyl azides. • α-Iodotetralones affords the respective 2-amino-1,4-naphthoquinone derivatives. • It provides an easy access to 1,1-disubstituted cyclic α-amino acids. α - Sulfonamidation of β-ketoesters with sulfonyl azide has been developed for the first time using a catalytic amount of Ru(II) complex to produce the 1-oxo-2-(sulfonamido)-2,3-dihydro-1 H -indene-2-carboxylate and 1-oxo-2-(sulfonamido)-1,2,3,4-tetrahydronaphthalene-2-carboxylate derivatives in good yields. This method also works well with α-iodotetralones to afford the N -(1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulphonamide derivatives under similar conditions. [ABSTRACT FROM AUTHOR]