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Кухаренко, А. В.; Avramenko, G. V.

doi:10.1023/a:1013994718545

Cited by 4 publications

(3 citation statements)

References 5 publications

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“…The spectral data of previously reported 2′-hydroxychalcones (1a–1q) are given in the following reference articles 1a, 1e , 1g, 1j , 1b , 1c , 1d , 1f , 1h , 1i , 1k , 1l , 1m , 1n , 1o , 1p and 1q . The spectral data of all the synthesized pyrazolines ( 2a–2q) are given here:…”

Section: Results and Discussionmentioning

confidence: 99%

Synthesis and Evaluation of 1,3,5-Triaryl-2-Pyrazoline Derivatives as Potent Dual Inhibitors of Urease and α-Glucosidase Together with Their Cytotoxic, Molecular Modeling and Drug-Likeness Studies

Mehmood¹,

Sadiq²,

Alsantali

et al. 2022

ACS Omega

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In the present work, a concise library of 1,3,5triaryl-2-pyrazolines (2a−2q) was designed and synthesized by employing a multistep strategy, and the newly synthesized compounds were screened for their urease and α-glucosidase inhibitory activities. The compounds (2a−2q) were characterized using a combination of several spectroscopic techniques including FT-IR, 1 H NMR, 13 C NMR, and EI-MS. All the synthesized compounds, except compound 2i, were potent against urease as compared to the standard inhibitor thiourea (IC 50 = 21.37 ± 0.26 μM). These analogs disclosed varying degrees of urease inhibitory activities ranging from 9.13 ± 0.25 to 18.42 ± 0.42 μM. Compounds 2b, 2g, 2m, and 2q having IC 50 values of 9.36 ± 0.27, 9.13 ± 0.25, 9.18 ± 0.35, and 9.35 ± 0.35 μM, respectively, showed excellent inhibitory activity as compared to standard thiourea (IC 50 = 21.37 ± 0.26 μM). A kinetic study of compound 2g revealed that compound 2g inhibited urease in a competitive mode. Among the synthesized pyrazolines, the compounds 2c, 2k, 2m, and 2o exhibited excellent α-glucosidase inhibitory activity with the lowest IC 50 values of 212.52 ± 1.31, 237.26 ± 1.28, 138.35 ± 1.32, and 114.57 ± 1.35 μM, respectively, as compared to the standard acarbose (IC 50 = 375.82 ± 1.76 μM). The compounds (2a− 2q) showed α-glucosidase IC 50 values in the range of 114.57 ± 1.35 to 462.94 ± 1.23 μM. Structure−activity relationship revealed that the size and electron-donating or -withdrawing effects of substituents influenced the activities, which led to the urease and αglucosidase inhibiting properties. Compound 2m was a dual potent inhibitor against urease and α-glucosidase due to the presence of 2-CF 3 electron-withdrawing functionality on the phenyl ring. To the best of our knowledge, these synthetic compounds were found to be the most potent dual inhibitors of urease and α-glucosidase with minimum IC 50 values. The cytotoxicity of the compounds (2a−2q) was also investigated against human cell lines MCF-7 and HeLa. Compound 2l showed moderate cytotoxic activity against MCF-7 and HeLa cell lines. Moreover, in silico studies on most active compounds were also performed to understand the binding interaction of most active compounds with active sites of urease and α-glucosidase enzymes. Some compounds exhibited drug-like characteristics due to their lower cytotoxic and good ADME profiles.

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Section: Results and Discussionmentioning

confidence: 99%

Synthesis and Evaluation of 1,3,5-Triaryl-2-Pyrazoline Derivatives as Potent Dual Inhibitors of Urease and α-Glucosidase Together with Their Cytotoxic, Molecular Modeling and Drug-Likeness Studies

Mehmood¹,

Sadiq²,

Alsantali

et al. 2022

ACS Omega

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“…For general background to 3-hydroxy-2-phenyl-4H-chromene-4-one (flavonol) and its derivatives, see: Kukharenko & Avramenko (2001); Petković et al (2010); Roshal et al (1998Roshal et al ( , 2003; Sytnik et al (1994). For related structures, see: Belogh-Hergovich et al (1999); Farina et al (1995); Kaizer et al (2007); Okabe et al (2003).…”

Section: Related Literaturementioning

confidence: 99%

“…The structure of the crystalline product that was actually separated is presented here. It appears that not complexation but condensation of the two reagents, accompanied by the release of HF, takes place (Kukharenko & Avramenko, 2001) and a molecule of a formally zwitterionic canonical structure was produced. Crystal structures of various flavonol complexes have so far been reported (Farina & Yamin, 1995;Belogh-Hergovich et al, 1999;Okabe et al, 2003;Kaizer et al, 2007), but none of them have contained boron.…”

Section: Crystal Datamentioning

confidence: 99%

2,2-Difluoro-4-phenyl-1,3,2-dioxaborolo[4,5-c]chromen-5-ium-2-ide

2010

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In the crystal, the inversely oriented molecules of the title compound, C15H9BF2O3, form stacks along the a axis via π–π interactions between parallel phenylchromenium fragments. Linked by a network of C—H⋯F interactions, the stacks form layers in the ac plane that are dispersively stabilized in the crystal structure. Two F atoms bonded to the B atom are located in the plane perpendicular to the planar skeleton of the molecule made rigid by two intramolecular C—H⋯O interactions.

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Six-membered Rings with Two or More Heteroatoms with at least One Boron

Romanenko

Sotiropoulos

2008

Comprehensive Heterocyclic Chemistry III

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HAL is a multi-disciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

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Untitled

Cited by 4 publications

References 5 publications

Synthesis and Evaluation of 1,3,5-Triaryl-2-Pyrazoline Derivatives as Potent Dual Inhibitors of Urease and α-Glucosidase Together with Their Cytotoxic, Molecular Modeling and Drug-Likeness Studies

Synthesis and Evaluation of 1,3,5-Triaryl-2-Pyrazoline Derivatives as Potent Dual Inhibitors of Urease and α-Glucosidase Together with Their Cytotoxic, Molecular Modeling and Drug-Likeness Studies

2,2-Difluoro-4-phenyl-1,3,2-dioxaborolo[4,5-c]chromen-5-ium-2-ide

Six-membered Rings with Two or More Heteroatoms with at least One Boron

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