Synthesis, characterization, crystal structure, Hirshfeld interaction and bio-evaluation studies of 4-amino quinazoline sulfonamide derivatives

Kumar, Ashish; Kudva, Jyothi; Kumar, Shankar; Vishwanatha, U.; Kumar, Vasantha; Naral, Damodara

doi:10.1016/j.molstruc.2018.04.055

Cited by 14 publications

(4 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is likely that the NH signal is masked under water of DMSO, while the aminophosphonate NH group appears upfield at ≈ 10 ppm. A sim-ilar observation has been documented for sulfisoxazole derivatives [60].…”

Section: Chemistrymentioning

confidence: 76%

Microwave-assisted synthesis of novel sulfonamide-based compounds bearing α-aminophosphonate and their antimicrobial properties

Sabry

Mohamed

Ewies

et al. 2022

Journal of Molecular Structure

View full text Add to dashboard Cite

Section: Chemistrymentioning

confidence: 76%

Microwave-assisted synthesis of novel sulfonamide-based compounds bearing α-aminophosphonate and their antimicrobial properties

Sabry

Mohamed

Ewies

et al. 2022

Journal of Molecular Structure

View full text Add to dashboard Cite

“…They are investigated in the current study for the pursuit to recognise effectual inhibitors to guard the mild steel against deteriorating in a corrosive environment. The distinctiveness of these inhibitors is they have exhibited antimicrobial, antitubercular and antifungal biological activities owing to the presence of the quinazoline‐sulfonamide and pyrimidine moiety [13–14] . They have exhibited superior antibacterial action against B. subtilis than the standard drug Ciprofloxacin having a minimal inhibitory concentration (MIC) of 2.0 μg/mL to a MIC of 0.8 μg/mL for PQS and 1.6 μg/mL for MQS.…”

Section: Introductionmentioning

confidence: 99%

“…The distinctiveness of these inhibitors is they have exhibited antimicrobial, antitubercular and antifungal biological activities owing to the presence of the quinazoline-sulfonamide and pyrimidine moiety. [13][14] They have exhibited superior antibacterial action against B. subtilis than the standard drug Ciprofloxacin having a minimal inhibitory concentration (MIC) of 2.0 μg/mL to a MIC of 0.8 μg/mL for PQS and 1.6 μg/mL for MQS. The non-toxic nature of PQS and MQS is verified by their excellent ADME parameters and studies carried out on red blood cells by hemolytic assay at higher concentrations.…”

Section: Introductionmentioning

confidence: 99%

Experimental and Theoretical Approach for the Corrosion Deceleration of Mild Steel in Hydrochloric Acid Medium by Two Sulfonamide Derivatives

Dsouza,

Kudva,

Kumar

et al. 2024

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

In the pursuit to find corrosion inhibitors of superior efficacy, N‐(pyrimidin‐2‐yl)‐4‐[(quinazoline‐4‐yl)amino]benzene‐1‐sulfonamide (PQS) and N‐(4‐methylpyrimidin‐2‐yl)‐4‐[(quinazoline‐4‐yl)amino]benzene‐1‐sulfonamide (MQS) are the two new sulfonamides employed, which have decelerating effect on mild steel (MS) corrosion in a medium 0.5 M HCl and were found to have an efficiency of 98.7 % and 96.8 % respectively (303 K for 40 ppm concentration) deliberated through the electrochemical techniques (PDP and EIS). The inhibitory efficacy relies on the temperature of the solution and inhibitor concentration. PQS had greater stability than MQS at higher temperatures which is indicative in the obtained experimental data. The relative adsorption process was in consonance with the Langmuir adsorption isotherm. The SEM, EDS, FT‐IR, and AFM analysis validated PQS and MQS to form a barrier on MS, opposing corrosion. The potential energy surfaces (PES) scan and a theoretical study for PQS and MQS were probed employing density functional theory (DFT) at B3LYP/6‐311+G(d, p) basis set level that explicated the formation of a complex between the sulfonamides and MS. The corrosion inhibition efficiency of PQS and MQS inferred from experimental and theoretical data comply, making them credible corrosion inhibitors.

show abstract

“…Disparate from the preceding reports, our report administers the incorporation of the sulfonamide moiety. Sulfonamides comprise of a remarkable category of medicinally efficient derivatives and possess several biological activities, such as antimicrobial [6,7,8,9,10], antiviral [11], insulin-releasing [12,13,14], anti-carbonic anhydrase [15,16,17], hypoglycemic [18], anti-inflammatory [19], antiglaucoma [20,21], anti-tumor [22,23,24] activities and effects. Additionally, pyrazole and pyrimidine nuclei are pharmacophoric scaffolds and exemplify a group of heterocyclic compounds with a large range of biological applications, including: antimicrobial [25,26,27,28,29,30,31,32,33,34,35,36], anticancer [37,38,39,40,41,42,43,44,45,46], analgesic and anti-inflammatory [47,48], antileishmanial [49,50,51], and antimalarial activities [50,51,52].…”

Section: Introductionmentioning

confidence: 99%

Rational Design and Synthesis of Diverse Pyrimidine Molecules Bearing Sulfonamide Moiety as Novel ERK Inhibitors

Halawa

Eskandrani

Elgammal

et al. 2019

IJMS

View full text Add to dashboard Cite

Protein kinases orchestrate diverse cellular functions; however, their dysregulation is linked to metabolic dysfunctions, associated with many diseases, including cancer. Mitogen-Activated Protein (MAP) kinase is a notoriously oncogenic signaling pathway in human malignancies, where the extracellular signal-regulated kinases (ERK1/2) are focal serine/threonine kinases in the MAP kinase module with numerous cytosolic and nuclear mitogenic effector proteins. Subsequently, hampering the ERK kinase activity by small molecule inhibitors is a robust strategy to control the malignancies with aberrant MAP kinase signaling cascades. Consequently, new heterocyclic compounds, containing a sulfonamide moiety, were rationally designed, aided by the molecular docking of the starting reactant 1-(4-((4-methylpiperidin-1-yl)sulfonyl)phenyl)ethan-1-one (3) at the ATP binding pocket of the ERK kinase domain, which was relying on the molecular extension tactic. The identities of the synthesized compounds (4–33) were proven by their spectral data and elemental analysis. The target compounds exhibited pronounced anti-proliferative activities against the MCF-7, HepG-2, and HCT-116 cancerous cell lines with potencies reaching a 2.96 μM for the most active compound (22). Moreover, compounds 5, 9, 10b, 22, and 28 displayed a significant G2/M phase arrest and induction of the apoptosis, which was confirmed by the cell cycle analysis and the flow cytometry. Thus, the molecular extension of a small fragment bounded at the ERK kinase domain is a valid tactic for the rational synthesis of the ERK inhibitors to control various human malignancies.

show abstract

Synthesis, characterization, crystal structure, Hirshfeld interaction and bio-evaluation studies of 4-amino quinazoline sulfonamide derivatives

Cited by 14 publications

References 33 publications

Microwave-assisted synthesis of novel sulfonamide-based compounds bearing α-aminophosphonate and their antimicrobial properties

Microwave-assisted synthesis of novel sulfonamide-based compounds bearing α-aminophosphonate and their antimicrobial properties

Experimental and Theoretical Approach for the Corrosion Deceleration of Mild Steel in Hydrochloric Acid Medium by Two Sulfonamide Derivatives

Rational Design and Synthesis of Diverse Pyrimidine Molecules Bearing Sulfonamide Moiety as Novel ERK Inhibitors

Contact Info

Product

Resources

About