RESUMEN
An Indane-1-one derivative 11-(1-benzyl-1H-indol-3-yl)-10,12-dihydrodiindeno[1,2-b:2',1'-e]-pyridine (BDP) has been synthesized by the reaction of Indan-1-one with 1-benzyl-1H-indole-3-carbaldehyde. FT-IR, 1H-NMR, 13N-NMR and Mass spectroscopic techniques has been used to confirmed the structure of BDP. The observed photophysical changes in BDP across various solvents were associated. The impact of various interactions on photophysical parameters, including Stokes shift, dipole moment, oscillator strength, and fluorescence quantum yields, has been assessed in relation to solvent polarity. Moreover, BDP demonstrates potential as a selective fluorescent chemosensor for detecting Fe3+ ion within a range of cations in an aqueous DMSO environment. A thorough investigation into the recognition mechanism of BDP towards Fe3+ ion has been conducted using Benesi-Hildebrand and Stern-Volmer, measurements. BDP forms a 2:1 complex with the Fe3+ ion, exhibiting fluorescent quenching behaviour.
RESUMEN
A new series of isatin-linked benzenesulfonamide derivatives (9a-w) were synthesized using the tail approach and assayed for their inhibitory potency against four different human carbonic anhydrase (hCA) isoforms, hCA I, II, IX, and XII. Most of these synthesized compounds exhibited interesting inhibition potency against isoforms hCA I, IX, and XII in the nanomolar range and by taking the standard drug acetazolamide. The most potent compounds in the case of hCA I were 9c (435.8 nM) and 9s (956.4 nM), for hCA IX, 9a (60.5 nM), 9d (95.6 nM), 9g (92.1 nM), and 9k (75.4 nM), and for hCA XII, 9p (84.5 nM). However, these compounds showed more selectivity toward hCA IX over hCA I, II, and XII. Thus, these compounds can be further developed as potential lead molecules for the development of isoform-selective hCA IX inhibitors with further structural modifications.
Asunto(s)
Bencenosulfonamidas , Inhibidores de Anhidrasa Carbónica , Anhidrasas Carbónicas , Diseño de Fármacos , Sulfonamidas , Inhibidores de Anhidrasa Carbónica/farmacología , Inhibidores de Anhidrasa Carbónica/síntesis química , Inhibidores de Anhidrasa Carbónica/química , Humanos , Relación Estructura-Actividad , Sulfonamidas/farmacología , Sulfonamidas/síntesis química , Sulfonamidas/química , Anhidrasas Carbónicas/metabolismo , Estructura Molecular , Isoenzimas/antagonistas & inhibidores , Isoenzimas/metabolismo , Isatina/farmacología , Isatina/química , Isatina/síntesis química , Relación Dosis-Respuesta a DrogaRESUMEN
This review basically concerned with the application of different Schiff bases (SB) based fluorimetric (turn-off and turn-on) and colorimetric chemosensors for the detection of heavy metal cations particularly Al(III), Fe(III), and Cr(III) ions. Chemosensors based on Schiff bases have exhibited outstanding performance in the detection of different metal cations due to their facile and in-expensive synthesis, and their excellent coordination ability with almost all metal cations and stabilize them in different oxidation states. Moreover, Schiff bases have also been used as antifungal, anticancer, analgesic, anti-inflammatory, antibacterial, antiviral, antioxidant, and antimalarial etc. The Schiff base also can be used as an intermediate for the formation of various heterocyclic compounds. In this review, we have focused on the research work performed on the development of chemosensors (colorimetric and fluorometric) for rapid detection of trivalent metal cations particularly Al(III), Fe(III), and Cr(III) ions using Schiff base as a ligand during 2020-2022.
RESUMEN
A donor-π-acceptor (D-π-A) chromophore, 2-amino-4-(9-ethyl-9H-carbazol-3-yl)-8-methoxy-5,6-dihydrobenzo[h]quinoline-3-carbonitrile (AEDQ) was synthesized from the condensation of 6-methoxy-3,4-dihydronaphthalen-1(2H)-one, 9-ethyl-9H-carbazole-3-carbaldehyde, malononitrile and NH4OAc in ethanol. Spectroscopic techniques and elemental analysis were employed to establish the structure of AEDQ. Photophysical parameters and fluorescence quantum yield were calculated in the different polarity solvents to evaluate the interactions of the solvent with AEDQ chromophore. Further, the interaction of the AEDQ with cationic and anionic surfactants (CTAB, SDS) were also evaluated by using fluorescence spectroscopy techniques. The intensity of the fluorescence spectrum increased as the concentration of surfactants increased, suggesting that strong interaction occurs between AEDQ with surfactants, and this interaction arises from electrostatic forces. As a result, the AEDQ chromophore could be used to determine the CMC of surfactants. The disc diffusion and minimal inhibitory concentration (MIC) technique were used to test in-vitro antibacterial activity against Gram +ve and Gram -ve bacteria, and the results are compared with the standard drug, tetracycline. AEDQ also showed good ADMET, pharmacokinetics and drug-likeness properties, which are desirable for a good drug candidate. The molecule also fits well in the DNA gyrase A active pocket site with the binding free energy of -17.92 kcal/mol, which testifies its good antibacterial activity.
Asunto(s)
Antibacterianos/farmacología , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Compuestos Heterocíclicos/farmacología , Microondas , Quinolinas/farmacología , Antibacterianos/síntesis química , Antibacterianos/química , Relación Dosis-Respuesta a Droga , Compuestos Heterocíclicos/síntesis química , Compuestos Heterocíclicos/química , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Quinolinas/síntesis química , Quinolinas/química , Relación Estructura-ActividadRESUMEN
The coumarin is one of the most promising classes of non-classical carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. In continuation of our ongoing work on search of coumarin based selective carbonic anhydrase inhibitors, a new series of 6-aminocoumarin based 16 novel analogues of coumarin incorporating thiazole (4a-p) have been synthesized and studied for their hCA inhibitory activity against a panel of human carbonic anhydrases (hCAs). Most of these newly synthesized compounds exhibited interesting inhibition constants in the nanomolar range. Among the tested compounds, the compounds 4f having 4-methoxy substitution exhibited activity at 90.9 nM against hCA XII isoform. It is noteworthy to see that all compounds were specifically and selectively active against isoforms hCA IX and hCA XII, with Ki under 1000 nM range. It is anticipated that these newly synthesized coumarin-thiazole hybrids (4a-p) may emerge as potential leads candidates against hCA IX and hCA XII as selective inhibitors compared to hCA I and hCA II.