A synergistic investigation of azo-thiazole derivatives incorporating thiazole moieties: a comprehensive exploration of their synthesis, characterization, computational insights, solvatochromism, and multimodal biological activity assessment

Muhammed Aziz, Dara; Hassan, Sangar Ali; Amin, Alla Ahmad M.; Abdullah, Media Noori; Qurbani, Karzan; Aziz, Shujahadeen B.

doi:10.1039/d3ra06469g

Cited by 13 publications

(2 citation statements)

References 78 publications

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“…Due to the properties like adaptability, simplicity, and functionality, SBs are highly important. [8] SBs have gained the attention of the scientific community due to their broad-spectrum of biological applications such as antimicrobial, [9] cytotoxic, antioxidant, [9,10] antiinflammatory, [11] antibacterial, [12] anti-tubercular, [13] antiviral, [14] anticonvulsant, [15] and antidiabetic [16] activities.…”

Section: Introductionmentioning

confidence: 99%

Biological Activities, DFT and Molecular Docking Studies of Novel Schiff Bases Derived from Sulfamethoxypyridazine

Wajid,

Uzair,

Muhammad

et al. 2024

ChemistrySelect

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The present study reported the synthesis and biological activities of sulfamethoxypyridazine (SMPR) Schiff bases (SBs) with different aromatic aldehydes. The antimicrobial potential of SBs against various pathogenic strains (S. epidermidis, E. coli, S. agalactiae, S. aureus, S. typhi, K. pneumoniae, C. albicans, and C. tropicalis) was explored by disc diffusion method. The antidiabetic potential was monitored by inhibition of α‐amylase, α‐glucosidase, and anti‐inflammatory activity was studied by protein denaturation assay. The binding of protein with SBs was determined by MOE docking. The synthesized SBs reveal significant antimicrobial potential against all strains (p values<0.0001) better than the parent drug SMPR but less than amoxicillin. The synthesized SBs exhibited reasonable inhibition potential against α‐glucosidase, α‐amylase, and anti‐inflammatory activity. The derivative 10 a depicted antioxidant (IC50 value 12.18 μg/mL) and anti‐inflammatory (IC50 value 49.37 μg/mL) even better than standard ascorbic acid and diclofenac sodium (IC50 values 49.92 and 123.81 μg/mL), respectively. Molecular docking results revealed that synthesized SBs have good binding affinities towards different receptor proteins and results support our experimental results. The electronic properties have been calculated using density function theory (DFT) to determine the chemical reactivity of studied compounds. The low energy gap between Frontier Molecular Orbitals (FMOs) revealed the significant chemical reactivity of compounds 8 a and 10 a, among other compounds.

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Section: Introductionmentioning

confidence: 99%

Biological Activities, DFT and Molecular Docking Studies of Novel Schiff Bases Derived from Sulfamethoxypyridazine

Wajid,

Uzair,

Muhammad

et al. 2024

ChemistrySelect

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“…The incorporation of nitrogen atoms within the heterocyclic ring imparts unique electronic and steric properties, influencing their interactions with biological macromolecules. [16][17][18][19] Consequently, heterocyclic compounds have emerged as key components in the synthesis of therapeutics for a wide range of diseases, including cancer, [20] infectious diseases, and neurological disorders. [21][22][23][24][25] Numerous efforts have been made to enhance the urease inhibitory potency and selectivity of existing azole drugs by modifying their structures.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Evaluation of Tetrazole Derivatives with Pyrrole‐2,5‐Dione Moieties as Urease Inhibitors: Exploring Structure‐Activity Relationships and Computational Insights

Muhammed Aziz,

Ali Hassan

2024

ChemistrySelect

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A series of Tetrazole derivatives containing pyrrole‐2,5‐dione groups (5 a–e) were synthesized and comprehensively characterized using HRMS, FT‐IR, and 1H−, 13C‐NMR spectroscopic techniques. These compounds were evaluated for their ability to inhibit urease activity in vitro, demonstrating remarkable inhibitory potential with IC50 values ranging from 4.325±1 to 18.28±1 μM, surpassing the standard thiourea (IC50=17.386±1 μM). Notably, compounds 5 b (IC50=4.325±1 μM), 5 e (IC50=7.411±1 μM), 5 c (IC50=9.313±1 μM), and 5 a (IC50=10.46±1 μM) exhibited notably higher activity compared to the standard thiourea. In our exploration of the structure‐activity relationship (SAR), we investigated the impact of differently substituted aryl rings on inhibitory potential. Our results highlight the crucial role of substituent positioning on the aryl ring, independent of the nature of the substituents. Additionally, computational studies were conducted on all compounds, supporting our experimental findings. Molecular docking simulations revealed a strong correlation between biological evaluation results and computational predictions, affirming the promising inhibitory activity of the compounds.

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Design and development of a novel Co‐MOF catalyst for sustainable pyrimidine synthesis via the Biginelli reaction

Aziz

2024

Applied Organom Chemis

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In this study, we introduce a novel porous metal–organic framework named Co2(bbda)2(DMF)2·5H2O, or MOF‐UoR‐1, synthesized via hydrothermal techniques employing a unique Schiff base ligand. The framework underwent comprehensive characterization, confirming its microporous nature through gas‐sorption measurements. MOF‐UoR‐1 demonstrated remarkable efficacy as a catalyst for the one‐step synthesis of pyrimidine analogs. Structural validation of the synthesized pyrimidines was accomplished via 1H‐nuclear magnetic resonance (NMR) and Fourier transform infrared (FTIR) analyses. Through systematic experimentation, the optimal catalyst dosage (40 mg) was determined, showcasing its effectiveness across various aldehydes, 1,3‐carbonyl compounds, and urea substrates. Noteworthy is the broad applicability of this environmentally friendly protocol, which offers advantages such as high yields (96%), rapid reaction times (90 min), straightforward product isolation, and product purity without necessitating column chromatography. Furthermore, the catalytic integrity of the framework remained intact, enabling its reuse without compromising performance. This research presents a promising approach for the synthesis of pyrimidine derivatives, with significant implications for sustainable and efficient chemical synthesis methodologies.

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A synergistic investigation of azo-thiazole derivatives incorporating thiazole moieties: a comprehensive exploration of their synthesis, characterization, computational insights, solvatochromism, and multimodal biological activity assessment

Abstract: In the present study, a novel series of azo-thiazole derivatives (3a–c) containing a thiazole moiety was successfully synthesized.

Cited by 13 publications

References 78 publications

Biological Activities, DFT and Molecular Docking Studies of Novel Schiff Bases Derived from Sulfamethoxypyridazine

Biological Activities, DFT and Molecular Docking Studies of Novel Schiff Bases Derived from Sulfamethoxypyridazine

Synthesis, Characterization, and Evaluation of Tetrazole Derivatives with Pyrrole‐2,5‐Dione Moieties as Urease Inhibitors: Exploring Structure‐Activity Relationships and Computational Insights

Design and development of a novel Co‐MOF catalyst for sustainable pyrimidine synthesis via the Biginelli reaction

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