4‐[(1, 3‐Dioxoisoindolin‐2‐yl)methyl]benzenesulfonamide: Full Structural and Spectroscopic Characterization and Molecular Docking with Carbonic Anhydrase II

Gökçe, Halil; Öztürk, Nuri; Sert, Yusuf; El‐Azab, Adel S.; Alsaif, Nawaf A.; Abdel‐Aziz, Alaa A.‐M.

doi:10.1002/slct.201802484

Cited by 18 publications

(3 citation statements)

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“…In the literature there are studies indicating that some benzenesulfonamide derivatives can interact with several biomolecules (Krishnamurthy et al, 2007;Zubrienė et al, 2017;Gökce et al, 2018); this phenomenon could involve different thermodynamic parameters such as such as free energy of binding, electrostatic energy, total intermolecular energy, and Van-Der Waals (vdW) + hydrogen bond (Hbond) + desolvation energy .…”

Section: Thermodynamic Parametersmentioning

confidence: 99%

Biological activity of a benzene sulfonamide on perfusion pressure and coronary resistance using an isolated rat heart model

Alvarez-Ramirez,

Figueroa-Valverde,

Rosas-Nexticapa

et al. 2024

Braz. J. of Sci.

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There are studies which indicate that some sulfonamide derivatives can produce changes in the cardiovascular system; however, their biological activity on perfusion presure and coronary resistance is not clear. The aim of this research was to evaluate the effect exerted by benzenesulfonamide, and their derivatives (2,5-dichloro- N-(4-nitro-phenyl)-benzene-sulfonamide, 2-hydrazino-carbonyl-benzenesulfonamide, 4-(2-amino-ethyl)-benze- ne-sulfonamide, and 4-[3-(4-nitro-phenyl)-ureido]-benzene- sulfonamide) on perfusion pressure and coronary reistance. To evaluate the biological activity of benzenesulfonamide and their derivatives on perfusion pressure and coronary reistance an isolated rat heart model was used. Furthermore, theoretical interaction of 4-(2-amino-ethyl)-benzenesul- fonamide with Calcium channel surface was determined using 6jp5 protein, nifedipine, amlodipine, verapamil and BayK 8644 as theoretical tools in a DockingServer program. The Results showed that 4-(2-amino-ethyl)-ben- zenesulfonamide decreased perfusion pressure and coronary resistance compared to benzenesulfonamide, 2,5-dichloro- N-(4-nitro-phenyl)-benzene-sulfonamide, 2-hydrazinocar- bonyl-benze-nesulfonamide, 4-[3-(4-nitro-phenyl)-ureido]- benenesulfonamide and the control conditions. Besides, theoretical data suggest that 4-(2-aminoethyl)benzenesulfo- namide could interact with aminoacid residues such as Glu614 and Ala320 involved in 6jp5 protein surface. This phenomenon could result in an ligand-Calcium channel complex formation to produce a decrease in perfusion pressure and vascular resistance. It is noteworthy that biological and experimental models used in this study is an invaluable research tool for investigating questions across the spectrum of physiologic functions of cardiovascular system such as perfusion pressure and coronary resistance

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Section: Thermodynamic Parametersmentioning

confidence: 99%

Biological activity of a benzene sulfonamide on perfusion pressure and coronary resistance using an isolated rat heart model

Alvarez-Ramirez,

Figueroa-Valverde,

Rosas-Nexticapa

et al. 2024

Braz. J. of Sci.

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“…Sulfonamide derivatives are a preferred class of COX-2 inhibitors and antitumor agents [7][8][9][10][11]. In addition, compounds incorporating sulfonamide fragments are highly used as CA inhibitors [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25]. Furthermore, SLC-0111 (Figure 1) is a sensitive inhibitor of CA IX/XII with a sulfonamide moiety (Phase I) for the rehabilitation of solid metastatic tumors via zinc metalloenzyme fixation [12,13,[26][27][28][29].…”

Section: Introductionmentioning

confidence: 99%

“…25 showed soft hCA XII inhibitory action (Ki, 46.1-89.4 nM, Table1). Structure-activity interactions of hCA XII activities with Ki values directed the following: (i) Ester 2 showed moderate hCA XII activity (Ki, 34.…”

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confidence: 99%

Carbonic Anhydrase Inhibition Activities of Schiff’s Bases Based on Quinazoline-Linked Benzenesulfonamide

et al. 2022

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Human carbonic anhydrase (CA, EC 4.2.1.1) (hCA) isoforms I, II, IX, and XII were investigated for their inhibitory activity with a series of new Schiff’s bases based on quinazoline scaffold 4–27. The hCA I isoform was efficiently inhibited by Schiff’s bases 4–6, 10–19, 22–27 and had an inhibition constant (Ki) value of 52.8–991.7 nM compared with AAZ (Ki, 250 nM). Amongst the quinazoline derivatives, the compounds 2, 3, 4, 10, 11, 16, 18, 24, 26, and 27 were proven to be effective hCA II inhibitors, with Ki values of 10.8–52.6 nM, measuring up to AAZ (Ki, 12 nM). Compounds 2–27 revealed compelling hCA IX inhibitory interest with Ki values of 10.5–99.6 nM, rivaling AAZ (Ki, 25.0 nM). Quinazoline derivatives 3, 10, 11, 13, 15–19, and 24 possessed potent hCA XII inhibitory activities with KI values of 5.4–25.5 nM vs. 5.7 nM of AAZ. Schiff’s bases 7, 8, 9, and 21 represented attractive antitumor hCA IX carbonic anhydrase inhibitors (CAIs) with KI rates (22.0, 34.8, 49.2, and 45.3 nM, respectively). Compounds 5, 7, 8, 9, 14, 18, 19, and 21 showed hCA I inhibitors on hCA IX with a selectivity index of 22.46–107, while derivatives 12, 14, and 18 showed selective hCA I inhibitors on hCA XII with a selectivity profile of 45.04–58.58, in contrast to AAZ (SI, 10.0 and 43.86). Compounds 2, 5, 7–14, 19–23, and 25 showed a selectivity profile for hCA II inhibitors over hCA IX with a selectivity index of 2.02–19.67, whereas derivatives 5, 7, 8, 13, 14, 15, 17, 20, 21, and 22 showed selective hCA II inhibitors on hCA XII with a selectivity profile of 4.84–26.60 balanced to AAZ (SI, 0.48 and 2.10).

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Synthesis, Experimental and Theoretical Characterization of Novel Pyrimidine‐5‐Carboxamides

Gümüş

Sert

Yalkın³

et al. 2019

ChemistrySelect

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Eight series of pyrimidine‐5‐carboxamides were synthesized and characterized by FT‐IR, 1H NMR, 13C NMR spectroscopies, HR‐MS and elemental analysis. To encourage experimental confirmations, molecular electronic structure calculations and harmonic vibrational frequencies of compounds (theoretical computations) were carried out with the DFT/B3LYP method at the 6–311G++(d,p) basis set. The selected important assignments‐computed harmonic vibrational wavenumbers of compounds were defined by using potential energy distribution (PED) analysis. The molecular electrostatic potential (MEP) surface analysis was examined to bring into the open nucleophilic and electrophilic reactive areas of the compounds. The highest occupied molecular orbitals and lowest unoccupied molecular orbitals (HOMOs and LUMOs) analyses were theoretically used for definition of electronic transitions corresponding to UV‐Vis. electronic absorption wavelengths. Additionally, for these series non‐linear optical properties (NLO) were investigated based on urea. Finally, in this manuscript molecular docking studies between macromolecule (receptor) and ligand interactions were carried out by using AutoDock Vina program. Obtained all outputs of new compounds were explained in different sections in‐depth.

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4‐[(1, 3‐Dioxoisoindolin‐2‐yl)methyl]benzenesulfonamide: Full Structural and Spectroscopic Characterization and Molecular Docking with Carbonic Anhydrase II

Cited by 18 publications

References 50 publications

Biological activity of a benzene sulfonamide on perfusion pressure and coronary resistance using an isolated rat heart model

Biological activity of a benzene sulfonamide on perfusion pressure and coronary resistance using an isolated rat heart model

Carbonic Anhydrase Inhibition Activities of Schiff’s Bases Based on Quinazoline-Linked Benzenesulfonamide

Synthesis, Experimental and Theoretical Characterization of Novel Pyrimidine‐5‐Carboxamides

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