Design, synthesis and anticancer evaluation of 1,2,4-thiadiazole linked benzoxazole-quinazoline derivatives

Perupogu, Neerada; Krishna, Ch. Murali; Ramachandran, D.

doi:10.1016/j.cdc.2020.100482

Cited by 5 publications

(1 citation statement)

References 43 publications

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“…Quinazolines have a broad range of pharmacological applications, in addition to their low toxicity profiles [ 3 ]. Quinazoline frameworks have great pharmacological activities as antioxidant [ 7 , 8 , 9 ], antidiabetic [ 10 , 11 , 12 ], antibacterial [ 13 , 14 , 15 ], antiviral [ 16 , 17 , 18 ], antimicrobial [ 19 , 20 , 21 ], anticancer [ 22 , 23 ], antihistaminic [ 24 , 25 , 26 ], antidiuretic [ 27 , 28 ], antitubercular [ 29 , 30 , 31 ], and anti-inflammatory [ 32 , 33 , 34 ] agents. Quinazolinones are a type of quinazoline derivative that are biologically active in the same way as quinazoline [ 35 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray Structure, Hirshfeld, DFT and Biological Studies on a Quinazolinone-Nitrate Complex

et al. 2022

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The reaction of 4-hydroxyquinazoline (4HQZ) with aqueous solution of nitric acid afforded the corresponding quinazolinone-nitrate (4HQZN) complex in very good yield. The crystal structure of 4HQZN was determined and its structural and supramolecular structural aspects were analyzed. 4HQZN crystallized in the space group P21/c and monoclinic crystal system with one [4HQZ-H]+[NO3]− formula and Z = 4. Its supramolecular structure could be described as a 2D infinite layers in which the 4HQZN molecules are connected via N-H…O and C-H…O hydrogen bridges. Using DFT calculations, the relative stability of five suggested isomers of 4HQZN were predicted. It was found that the medium effects have strong impact not only on the isomers’ stability but also on the structure of the 4HQZN. It was found that the structure of 4HQZN in DMSO and methanol matched well with the reported X-ray structure which shed the light on the importance of the intermolecular interactions on the isomers’ stability. The structure of 4HQZN could be described as a proton transfer complex in which the nitrate anion acting as an e-donor whiles the protonated 4HQZ is an e-acceptor. In contrast, the structure of the isolated 4HQZN in gas phase and in cyclohexane could be described as a 4HQZ…HNO3 hydrogen bonded complex. Biological screening of the antioxidant, anticancer and antimicrobial activities of 4HQZ and 4HQZN was presented and compared. It was found that, 4HQZN has higher antioxidant activity (IC50 = 36.59 ± 1.23 µg/mL) than 4HQZ. Both of 4HQZ and 4HQZN showed cell growth inhibition against breast (MCF-7) and lung (A-549) carcinoma cell lines with different extents. The 4HQZ has better activity with IC50 of 178.08 ± 6.24 µg/mL and 119.84 ± 4.98 µg/mL, respectively. The corresponding values for 4HQZN are 249.87 ± 9.71 µg/mL and 237.02 ± 8.64 µg/mL, respectively. Also, the antibacterial and antifungal activities of 4HQZN are higher than 4HQZ against all studied microbes. The most promising result is for 4HQZN against A. fumigatus (MIC = 312.5 mg/mL).

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Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray Structure, Hirshfeld, DFT and Biological Studies on a Quinazolinone-Nitrate Complex

et al. 2022

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Quinazoline derivatives and hybrids: recent structures with potent bioactivity

Bala,

Asiri,

El-Shishtawy

2024

Med Chem Res

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Synthesis, Properties, and Biological Applications of 1,2,4-Thiadiazoles

Mohite,

Bhoge,

Dengale

et al. 2024

S-Heterocycles

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This chapter provides a comprehensive overview of recent advances in the preparation and biological applications of 1,2,4-thiadiazole, a versatile heterocyclic compound with diverse pharmacological properties. This chapter begins with the exploration of various synthetic strategies, ranging from traditional methods to sustainable and green approaches, highlighting their impact on synthetic efficiency and environmental considerations. The focus is then shifted to the biological applications of 1,2,4-thiadiazole derivatives, which show pharmacological activities, such as antioxidant, antimicrobial, anti-inflammatory, and anticancer properties. Structure–activity relationship studies are discussed which offer valuable insights into the molecular features influencing the bioactivity of these compounds. The relevance of 1,2,4-thiadiazoles in addressing contemporary health challenges is emphasized, and the potential of this scaffold for drug design and development is underscored. The documented pharmacological effects of 1,2,4-thiadiazole derivatives highlight their promising role in the development of therapeutic agents with enhanced efficacy and selectivity. The optimization of synthetic routes, scalability improvements, and exploration of innovative drug delivery systems are identified as crucial areas for future investigation. Ultimately, this chapter positions 1,2,4-thiadiazole as a pivotal candidate in the medicinal field, poised to make significant contributions to the pharmaceutical landscape.

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Design, synthesis and anticancer evaluation of 1,2,4-thiadiazole linked benzoxazole-quinazoline derivatives

Cited by 5 publications

References 43 publications

Synthesis, X-ray Structure, Hirshfeld, DFT and Biological Studies on a Quinazolinone-Nitrate Complex

Synthesis, X-ray Structure, Hirshfeld, DFT and Biological Studies on a Quinazolinone-Nitrate Complex

Quinazoline derivatives and hybrids: recent structures with potent bioactivity

Synthesis, Properties, and Biological Applications of 1,2,4-Thiadiazoles

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