An overview of triazoloquinazolines: Pharmacological significance and recent developments

Abuelizz, Hatem A.; Al‐Salahi, Rashad

doi:10.1016/j.bioorg.2021.105263

Cited by 20 publications

(111 citation statements)

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“…Triazole benzoic acid hybrids (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were described in our previous work as predicted in Scheme 1 and Table 1. Parents 1 and 2 resulted from the reaction of N-cyanoimido(dithio)carbonates with 4-hydrazinobenzoic acid.…”

Section: Resultsmentioning

confidence: 99%

“…The most stable geometries have been selected for preparation of the radical input geometries and further investigation (Figure S1). Three or fewer initial proposals per compound (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14), have been examined for this purpose.…”

Section: Dft Study 351 Geometry Optimizationmentioning

confidence: 99%

“…Most drugs and biologically relevant compounds possess triazole nucleus privileged precise in their pharmacological purposes [1][2][3]. Triazole is a biologically imperious platform known to be related with significant pharmacological activities such as antidepressant [4], anticonvulsant [5,6], antioxidant [7,8], antimicrobial [9,10], antiviral [11][12][13], analgesic [14], anti-inflammatory [14,15], hypoglycemic [16], anticancer [17,18], antihistamine [19,20], pesticidal-insecticidal [21,22], CNS depressant [23], and antihypertensive properties [24,25].…”

Section: Introductionmentioning

confidence: 99%

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Biological Evaluation of 4-(1H-triazol-1-yl)benzoic Acid Hybrids as Antioxidant Agents: In Vitro Screening and DFT Study

et al. 2021

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Fourteen triazole benzoic acid hybrids were previously characterized. This work aimed to screen their in vitro antioxidant activity using different assays, i.e., DPPH (1,1-diphenyl-1-picrylhydrazyl), reducing the power capability, FRAP (ferric reducing antioxidants power) and ABTS (2,2′-azino-bis(3-ethylben zothiazoline-6-sulfonate) radical scavenging. The 14 compounds showed antioxidant properties in relation to standard BHA (butylated hydroxylanisole) and Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid). Higher antioxidant activity was observed by the parent (1) at a concentration of 100 µg/mL (89.95 ± 0.34 and 88.59 ± 0.13%) when tested by DPPH and ABTS methods in relation to BHA at 100 µg/mL (95.02 ± 0.74 and 96.18 ± 0.33%). The parent (2) demonstrated remarkable scavenging activity when tested by ABTS (62.00 ± 0.24%), however, 3 was less active (29.98 ± 0.13%). Compounds 5, 6, 9, and 11 exhibited good scavenging activity compared to 1. DFT studies were performed using the B3LYP/6-311++g (2d,2p) level of theory to evaluate different antioxidant descriptors for the targets. Three antioxidant mechanisms, i.e., hydrogen atom transfer (HAT), sequential electron transfer proton transfer (SETPT) and sequential proton loss electron transfer (SPLET) were suggested to describe the antioxidant properties of 1–14. Out of the 14 triazole benzoic acid hybrids, 5, 9, 6, and 11 showed some good theoretical results, which were in agreement with some experimental outcomes. Based on the computed (PA and ETE) and (BDE and IP) values in (SPLET) and (HAT and SETPT) mechanisms, respectively, compound 9 emerged has having good antioxidant activity.

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Section: Resultsmentioning

confidence: 99%

Section: Dft Study 351 Geometry Optimizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Biological Evaluation of 4-(1H-triazol-1-yl)benzoic Acid Hybrids as Antioxidant Agents: In Vitro Screening and DFT Study

et al. 2021

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“…5 Both triazole and fused triazole moieties play a pivotal role in the inhibitory activity and selectivity of various targets. 191 Tyrosine kinase (TK) acts as a switch for several signaling pathways within cells, and its mutations generally lead to diseases, especially cancer. TK inhibitors (TKIs) are targeted for the treatment of cancers, but the extensive usage of TKIs is a major factor contributing to drug resistance, which significantly impacts their clinical efficacies.…”

Section: Triazoles and Bioisosterismmentioning

confidence: 99%

Triazoles in Medicinal Chemistry: Physicochemical Properties, Bioisosterism, and Application

Guan,

Xing,

Wang

et al. 2024

J. Med. Chem.

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Triazole demonstrates distinctive physicochemical properties, characterized by weak basicity, various dipole moments, and significant dual hydrogen bond acceptor and donor capabilities. These features are poised to play a pivotal role in drug−target interactions. The inherent polarity of triazole contributes to its lower logP, suggesting the potential improvement in water solubility. The metabolic stability of triazole adds additional value to drug discovery. Moreover, the metal-binding capacity of the nitrogen atom lone pair electrons of triazole has broad applications in the development of metal chelators and antifungal agents. This Perspective aims to underscore the unique physicochemical attributes of triazole and its application. A comparative analysis involving triazole isomers and other heterocycles provides guiding insights for the subsequent design of triazoles, with the hope of offering valuable considerations for designing other heterocycles in medicinal chemistry. ■ SIGNIFICANCE AND IMPACT• Significance: Triazole rings, including 1,2,3-triazole and 1,2,4-triazole, are pivotal in drug design due to their unique physicochemical properties, serving as versatile alternatives to various aromatic rings and functional groups.• Impact: It emphasizes the influence of the physicochemical properties of triazoles while providing comparative data with other frequently employed pharmacophores in medicinal chemistry. • Innovation: This Perspective discusses the influence of diverse physicochemical properties of triazoles and their strategic application in drug design.

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“…The class of heterocyclic compounds known as 1,2,4-triazolo [1,5-a]quinazolines has recently emerged as being of critical importance in the fields of medicinal chemistry and the creation of new drugs. These compounds possess the ability of a wide variety of biological functions and have demonstrated promise as potential therapeutic agents in a number of different disease categories [1]. Their pharmacological activities have shown evidence of a variety of different pharmacological activities, such as adenosine antagonist, anticancer, antiviral, antibacterial, antifungal, and anti-inflammatory behaviors [2,3].…”

Section: Introductionmentioning

confidence: 99%

Hirshfeld Surface Analysis and Density Functional Theory Calculations of 2-Benzyloxy-1,2,4-triazolo[1,5-a] quinazolin-5(4H)-one: A Comprehensive Study on Crystal Structure, Intermolecular Interactions, and Electronic Properties

Bakheit,

Abuelizz,

Al-Salahi

2023

Crystals

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This study employs a comprehensive computational analysis of the 2-benzyloxy-1,2,4-triazolo[1,5-a] quinazolin-5(4H)-one (ID code: CCDC 834498) to explore its intermolecular interactions, surface characteristics, and crystal structure. Utilizing the Hirshfeld surface technique and Crystal Explorer 17.5, the study maps the Hirshfeld surfaces for a detailed understanding of atom pair close contacts and interaction types. The study also investigates the compound’s electronic and optical characteristics using Frontier Molecular Orbital (FMO) analysis and Global Reactivity Parameters (GRPs). The compound is identified as electron-rich with strong electron-donating and accepting potential, indicating its reactivity and stability. Its band gap suggests Nonlinear Optical (NLO) attributes. The Molecular Electrostatic Potential (MEP) map reveals charge distribution across the compound’s surface. The computational methods’ reliability is validated by the low Mean Absolute Error (MAE) and Mean Squared Error (MSE) in the comparison of experimental and theoretical bond lengths and angles.

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An overview of triazoloquinazolines: Pharmacological significance and recent developments

Cited by 20 publications

References 98 publications

Biological Evaluation of 4-(1H-triazol-1-yl)benzoic Acid Hybrids as Antioxidant Agents: In Vitro Screening and DFT Study

Biological Evaluation of 4-(1H-triazol-1-yl)benzoic Acid Hybrids as Antioxidant Agents: In Vitro Screening and DFT Study

Triazoles in Medicinal Chemistry: Physicochemical Properties, Bioisosterism, and Application

Hirshfeld Surface Analysis and Density Functional Theory Calculations of 2-Benzyloxy-1,2,4-triazolo[1,5-a] quinazolin-5(4H)-one: A Comprehensive Study on Crystal Structure, Intermolecular Interactions, and Electronic Properties

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