Benzothiazolopyridine compounds: Facial synthesis, characterization, and molecular docking study on estrogen and progesterone receptors

Shirani, Mohammad Ali; Maleki, Mohammad Hassan; Asadi, Parvin; Dinari, Mohammad

doi:10.1016/j.molstruc.2021.130792

Cited by 14 publications

(8 citation statements)

References 49 publications

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“…The dipolarophiles (E)-2-(benzo [d]thiazol-2-yl)-3-(aryl)acrylonitriles 4a−g were prepared according to literature. 41 Computational Details. Geometry optimizations were computed on 1, 2, 3, 4a−g, 5a−g, and 6a−g in vacuum with density functional theory (DFT) using B3LYP exchange correlation functional 42 combined with Dunning's correlation consistent triple-ζ basis set (cc-pVTZ).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Study on Regio- and Diastereoselectivity of the 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide with 2-(Benzo[d]thiazol-2-yl)-3-(aryl)acrylonitrile: Synthesis, Spectroscopic, and Computational Approach

Hussein,

Moussa,

Al-Fahemi

et al. 2024

ACS Omega

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An unprecedented and efficient three-component 1,3-dipolar cycloaddition reaction using (E)-2-(benzo[d]thiazol-2-yl)-3-(aryl)acrylonitriles 4a–g and an in situ generated azomethine ylide 3 from isatin and N-methylglycine is described. The reaction exhibits exclusive regioselectivity, resulting in the formation of 3′-(benzo[d]thiazol-2-yl)-1′-methyl-2-oxo-4′-(aryl)spiro[indoline-3,2′-pyrrolidine]-3′-carbonitriles regioisomers through exo/endo approaches. The diastereoselectivity of the reaction is highly dependent on the substitution pattern of the phenyl ring in dipolarophiles 4a–g, leading to the formation of exo-/endo-cycloadducts in varying ratios. To understand the stereoselectivity, the transition state structures were optimized using the TS guess geometry with the QST3-based method. The reaction mechanism and regioselectivity were elucidated by evaluating global and local electrophilicity and nucleophilicity descriptors at the B3LYP/cc-pVTZ level of theory, along with considerations based on the HSAB principle. The analysis of global electron density transfer (GEDT) showed that the reactions are polar and electron density fluxes from azomethine ylide 3 toward dipolarophile 4a–g. It was found from the molecular electrostatic potential map (MESP) that at the more favorable transition state, approach of reactants locates the oppositely charged regions over each other resulting in attractive forces between the two fragments. The computational results are consistent with the experimental observations, confirming that the reactions proceed through an asynchronous one-step mechanism.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Study on Regio- and Diastereoselectivity of the 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide with 2-(Benzo[d]thiazol-2-yl)-3-(aryl)acrylonitrile: Synthesis, Spectroscopic, and Computational Approach

Hussein,

Moussa,

Al-Fahemi

et al. 2024

ACS Omega

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“…Molecular docking [24][25] was performed with Auto Dock 4. In all three directions, the grid box was considered large enough to allow the ligand to rotate freely to obtain the most stable conformation in the complex structure.…”

Section: Protein Ligand Dockingmentioning

confidence: 99%

Single‐Step Synthesis, Characterization, Molecular Docking Studies and In Vitro Analysis of Norethindrone Conjugates

Srivastava,

Kumar,

Pandey

et al. 2023

ChemistrySelect

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In the present work (17‐ethynyl‐13‐methyl‐3‐oxo‐2, 3, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17‐tetradecahydro‐1H‐cyclopenta[a]phenanthren‐17‐yl‐ethyl‐7‐methyl‐4‐oxo‐1,4‐dihydro‐1,8‐naphthyridine‐3‐carboxylate)and (17‐ethynyl‐13‐methyl‐3‐oxo‐2, 3, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17‐tetradecahydro‐1H‐cyclopenta[a]phenanthren‐17‐yl 2‐(4‐chlorophenoxy) acetate), anovel prodrugs of norethindrone have been synthesized. The structure of the synthesized compounds were characterized with the help of 1H, 13C NMR, UV, and IR spectroscopy.Norethindrone is used for contraception or hormone‐related conditions such as endometriosis and menopausal symptoms and to treat bacterial infections in a variety of pharmaceutical formulations. Molecular docking studies of the synthesized compounds explained the most probable interaction pattern with cyclooxygenase‐2 (1CX2),human estrogen receptor (2OCF) and RSK‐4N‐terminal kinase(6G77). Compound 2 & 3 possessedanti‐inflammatoryand cytotoxic activity besides contraceptive. Both thesynthesized compounds were found to be more potent than norethindrone as revealed from the binding energy and in‐vitro cytotoxic activity against lung cancer cells. Anti‐inflammatory and cytotoxic activity for norethindrone is reported for the first time.

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“…[14][15][16][17][18] In recent years, the use of stable nanocatalysts with simple design, recyclability, easy separation and low cost has attracted much attention. Nanocatalytic systems are used for synthesis of different heterocycles scaffold as a vital compounds in medicinal chemistry, [19] pollutant removal, [20] and reduction systems [21] because of the high efficiency and selective conversion. For the reduction of nitroaromatic compounds, numerous catalysts are used based upon metal nanoparticles, for instance, Cu, Ag, Ni, Pd, Pt, and Au.…”

Section: Introductionmentioning

confidence: 99%

Facile and green fabrication of copper‐based magnetically recoverable yolk–shell nanocatalysts with high catalytic performance for nitroaromatic reduction

Maleki

Dinari

Arameshian

2023

Applied Organom Chemis

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A simple method was reported to achieve a green yolk–shell Fe3O4@SiO2@CuO nanocatalysts (YS‐Fe3O4@SiO2@CuO). Glucose (G) and lactose (L), as a grafting agent, were applied for decorating CuO on the magnetic nanoparticles surface and then using calcination method, yolk–shell structure was obtained. Characterization of nanocatalysts was carried out using inductively coupled plasma–optical emission spectrometry (ICP‐OES), field emission scanning electron microscopy (FE‐SEM), transmission electron microscopy (TEM), energy‐dispersive X‐ray (EDX)‐Mapping, thermogravimetric analysis (TGA), X‐ray diffraction (XRD), Fourier transform infrared spectroscopy (FT‐IR), X‐ray photoelectron spectroscopy (XPS), Brunauer, Emmett, and Teller (BET), and vibrating sample magnetometer (VSM) analyses and the results confirmed the successful synthesis of these catalysis. The activity of the nanocatalysts were studied to reduce nitroaromatic compounds monitoring by UV–Vis spectra. In the model reaction, 4‐nitrophenol was reduced using YS‐Fe3O4@SiO2@CuO(G) and YS‐Fe3O4@SiO2@CuO(L), with the activity factors (k′) of 3218 and 2023 s−1 g−1, and rate constants (Kapp) of 0.56 and 1.19 min−1, respectively. The advantages of prepared nanocatalysts were good stability and high conversion. The magnetic property of nanocatalysts makes them easy to recover in multiple cycles.

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Benzothiazolopyridine compounds: Facial synthesis, characterization, and molecular docking study on estrogen and progesterone receptors

Cited by 14 publications

References 49 publications

Study on Regio- and Diastereoselectivity of the 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide with 2-(Benzo[d]thiazol-2-yl)-3-(aryl)acrylonitrile: Synthesis, Spectroscopic, and Computational Approach

Study on Regio- and Diastereoselectivity of the 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide with 2-(Benzo[d]thiazol-2-yl)-3-(aryl)acrylonitrile: Synthesis, Spectroscopic, and Computational Approach

Single‐Step Synthesis, Characterization, Molecular Docking Studies and In Vitro Analysis of Norethindrone Conjugates

Facile and green fabrication of copper‐based magnetically recoverable yolk–shell nanocatalysts with high catalytic performance for nitroaromatic reduction

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