Recent advances in triazole-benzenesulfonamide hybrids and their biological activities

Chander,; Monika,; Sharma, Pawan K.; Ram, Shobha

doi:10.1007/s00044-023-03052-8

Cited by 6 publications

(1 citation statement)

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“…[25][26][27] Our main efforts have been mainly devoted to the research and development of novel approaches for synthesizing new heterocyclic hybrid compounds, beginning with particular biologically functionalized constituents, [28][29][30][31][32][33][34][35] and exploring the biological significance of benzene sulfonamides, which constitute an important class of organic compounds with high potency and selectivity against parasitic, bacterial, fungal, and cancer cells, [36][37][38][39] along with the broad pharmacological spectrum of the 1,2,3-triazole nucleus, [40][41][42][43] resulting in their selection as preferred frameworks for library design and the generation of tailored therapeutic agents. [44][45][46][47] Furthermore, their possession of numerous functions in the structures has resulted in a resurgence of interest in improving their synergetic effects. 48 Human carbonic anhydrase IX (hCA-IX) is a transmembrane cell surface glycoprotein that is over-expressed in tumors under hypoxic conditions, which are key factors of the tumor microenvironment.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of chromene-1,2,3-triazole benzene sulfonamide hybrids as potent carbonic anhydrase-IX inhibitors against prostate cancer

Albelwi,

Nafie,

Albujuq

et al. 2024

RSC Med. Chem.

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Section: Introductionmentioning

confidence: 99%

Design and synthesis of chromene-1,2,3-triazole benzene sulfonamide hybrids as potent carbonic anhydrase-IX inhibitors against prostate cancer

Albelwi,

Nafie,

Albujuq

et al. 2024

RSC Med. Chem.

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Synthesis and biological evaluation of novel benzenesulfonamide incorporated thiazole–triazole hybrids as antimicrobial and antioxidant agents

Monika,

Chander,

Sharma

et al. 2023

Archiv der Pharmazie

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A library of 20 novel benzenesulfonamide incorporating thiazole tethered 1,2,3‐triazoles 1–4a–e was synthesized and screened for their antimicrobial, antioxidant, and cytotoxicity studies. Amoxicillin and fluconazole were used as reference antibacterial and antifungal drugs, respectively. Further, energies of frontier molecular orbitals were calculated for all the synthesized target compounds 1–4a–e to correlate electronic parameters with the observed biological results. Global reactivity descriptors, including highest occupied molecular orbitals‐lowest unoccupied molecular orbitals energy gap, electronegativity, chemical hardness, chemical softness, and electrophilicity index, were also calculated for the synthesized molecules. All the tested compounds possessed moderate to excellent antibacterial potency; however, 3d and 4d exhibited the overall highest antibacterial effect (minimum inhibitory concentration [MIC] values 5–11 µM) while 2c showed the highest antifungal effect (MIC value 6 µM). Compound 3c exhibited the highest antioxidant activity with a % radical scavenging activity value of 95.12. The cytotoxicity of the compounds 1–4a–e was also checked against an animal cell line and a plant seed germination cell line, and the compounds were found to be safe against both the tested cell lines.

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An operationally simple, one‐pot, convenient synthesis, and in vitro anti‐inflammatory activity of some new spirotriazolotriazine derivatives

El‐Saghier,

Enaili,

Abdou

et al. 2023

Journal of Heterocyclic Chem

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The wide biological actions of triazolotriazine hybrids, benzene‐sulfonamide derivatives, exhibit a good chance of displaying in vitro anti‐inflammatory effects. An operationally simple one‐pot, three‐component, and convenient synthesis method is used toward the synthesis of a series of diverse 2‐(2‐(4‐amino)‐1,3,5‐triazaspiro‐1,4‐dien‐2‐yl) hydrazinyl)‐N‐(4‐sulfamoylphenyl)‐2‐thioxoacetamides, which generated via reaction of 2‐hydrazinyl‐N‐(4‐sulfamoylphenyl)‐2‐thioxoacetamide, cyanoguanidine, and cyclic/acyclic ketones and were characterized by spectral analysis (IR, Nuclear Magnetic Resonance: 1H‐NMR, 13C‐NMR, and elemental analysis). The spirotriazolotriazine derivatives are obtained with up to 95% yield, and their structure–activity relationship was discussed. All compounds were tested for in vitro anti‐inflammatory potential using the inhibition of RBC hemolysis technique and COX inhibition assay. The results from RBC hemolysis technique demonstrated that almost all evaluated compounds exhibited significant in vitro anti‐inflammatory efficacy. More specifically, compounds 7, 8, and 12 have superior membrane stability over indomethacin as a standard drug. At concentrations of 400, 600, 800, and 1000 μg/mL, compound 12 demonstrated highly significant inhibition of RBC hemolysis with 95.2%, 97.3%, 98.9%, and 99.8%, respectively, compared with indomethacin at the same concentrations (94.5%, 97.3%, 98.5%, and 99.3%, respectively). COX assay indicated that compounds 7, 8, and 12 exhibited excellent COX‐2 inhibition percentage (98.51 ± 0.01, 98 ± 0.01, and 98.97 ± 0.06, respectively) at 150 μg/mL using indomethacin (97.3 ± 0.005). Furthermore, an investigation using molecular docking against COX‐2 (pdb ID: 5IKT) was used to analyze the anti‐inflammatory properties of all studied substances. When compared to indomethacin, molecular docking research showed a strong connection with the intended protein and an elevated docking score. According to in vitro anti‐inflammatory action and computational approach, they show promise as a therapeutic candidate for the treatment of inflammatory diseases.

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Recent advances in triazole-benzenesulfonamide hybrids and their biological activities

Cited by 6 publications

References 105 publications

Design and synthesis of chromene-1,2,3-triazole benzene sulfonamide hybrids as potent carbonic anhydrase-IX inhibitors against prostate cancer

Design and synthesis of chromene-1,2,3-triazole benzene sulfonamide hybrids as potent carbonic anhydrase-IX inhibitors against prostate cancer

Synthesis and biological evaluation of novel benzenesulfonamide incorporated thiazole–triazole hybrids as antimicrobial and antioxidant agents

An operationally simple, one‐pot, convenient synthesis, and in vitro anti‐inflammatory activity of some new spirotriazolotriazine derivatives

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