Synthesis, Molecular Docking and in Vitro Screening of Some Newly Synthesized Triazolopyridine, Pyridotriazine and Pyridine–Pyrazole Hybrid Derivatives

Flefel, Eman M.; El-Sofany, Walaa I.; El‐Shahat, Mahmoud; Naqvi, Arshi; Assirey, Eman

doi:10.3390/molecules23102548

Cited by 30 publications

(19 citation statements)

References 58 publications

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“…In continuation of our earlier interest on the synthesis of a wide range of applicable heterocyclic compounds [11,12,13,14,15,16,64,65,66,67,68,69,70,71,72,73,74,75,76,77], the starting compound 4-(4-aminophenyl)-1-thia-4-azaspiro [4.5]decan-3-one (1) was prepared by condensation between cyclohexanone, p-phenyllenediamine, and thioglycolic acid in dry toluene. Compound 1 was reacted with nitrogen nucleophiles such as hydrazine hydrate, phenylhydrazine, and/or thiosemicarbaxzide to give the hydrazones 2 – 4 , respectively.…”

Section: Resultsmentioning

confidence: 99%

“…As a continuation to our program directed towards the synthesis of useful chemotherapeutic agency [66,67,68,69,70,71,72,73,74,75,76,77,78], we decided to explore other spirothiazolidinone derivatives for multiple potential biological activities. The current study was designed to locate novel important scaffold spiro (cyclohexane-thiazolidine) derivatives that can inhibit human cancer targets MCF-7 and HepG-2.…”

Section: Introductionmentioning

confidence: 99%

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Development of a Novel Series of Anticancer and Antidiabetic: Spirothiazolidines Analogs

et al. 2019

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4-(4-Aminophenyl)-1-thia-4-azaspiro[4.5]decan-3-one 1 was prepared and allowed to react with nitrogen nucleophiles to give the corresponding hydrazones 2–4. Further, compound 1 underwent diazotization and afforded the parallel hydrazono derivative 5; moreover, compound 1 refluxed with active methylene derivatives yielded the corresponding aminospirothiazolo pyridine–carbonitrile derivative 6 and spirothiazolopyridinone–carbonitrile derivative 7. Condensation of spirothiazolidine 1 with 4-chlorobenzaldehyde gave the corresponding spiro arylidiene derivative 8, which was utilized as a component of Micheal addition to react with excess of nitrogen nucleophiles to yield novel ring frameworks 4-(3′-(4-chlorophenyl)–spiro [cyclohexane-1,5′-pyrazolo[3,4-d]thiazol]-6′(1′H)-yl)aniline (9) and 4-(3′-(4-chlorophenyl)-6′H- spiro[cyclohexane-1,5′-thiazolo[5,4-d]isoxazol]-6′-yl)aniline (10). Finally, when spirothiazolo pyridinone–carbonitrile derivative 7 sodium salt generated in situ was reacted with different alkyl halides, it produced the corresponding N-derivatives 12–16. Three compounds, 6, 14, and 16, showed high significantly anticancer activities compared with Doxorubicin® (positive control) against human breast carcinoma (MCF-7) and human liver carcinoma (HepG-2) cell lines. On the other hand, compounds 6 and 9 showed higher therapeutic indices for both of alpha-amylase inhibitor and alpha-glucosidase inhibitor than the other tested compounds compared with the antidiabetic Acarbose (positive control).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Development of a Novel Series of Anticancer and Antidiabetic: Spirothiazolidines Analogs

et al. 2019

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“…To examine the SAR studies [ 27 , 28 ]: Electron withdrawing group (-Cl) on the quinoline ring of 5f showed maximum antibacterial activity than other imidazoquinolines and reached the effectiveness of the standard. At high concentration (100 mg/disc), 5f demonstrated the higher activity against E. coli, K. pneumonia, S. paratyphi, S. typhi, M. butyricum than that of in standard (10 mg/disc).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, antibacterial, anti-oxidant and molecular docking studies of imidazoquinolines

Velmurugan

Don

Kannan

et al. 2021

Heliyon

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Quinoline and imidazole derivatives have been playing a significant role in functional bioactivities and were potentially used as antibacterial, antifungal, anticancer, and anti-inflammatory drugs. Owing to the limitation of drug resistance, herein we synthesized thio-, chloro-, and hydroxyl-functionalized various imidazoquinolines by molecular hybridization approach. All the imidazoquinoline derivatives were examined for their antibacterial activity against selected bacterial pathogens by the agar well diffusion method. In addition, the anti-oxidant efficacy of imidazoquinolines was also tested using ferric reducing antioxidant power (FRAP). Among them, electron-withdrawing (-Cl) substituent containing imidazoquinoline 5f showed higher antibacterial and antioxidant activities than other imidazoquinolines and reached the effectiveness of the standard. In addition, compounds 4f, 5e, and 3f showed moderate antibacterial activity and other derivatives displayed weak activity against various pathogens. Molecular docking studies were also performed on selected imidazoquinoline derivatives (3f, 4f, and 5f), which showed high docking score and strong binding energy values. These results revealed that thio-imidazoquinoline could assist as a prototype for the designing of multidrug-resistant antibiotics against various microbial organisms.

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“…They have been recognized as antifungal [ 1 , 2 , 3 , 4 ], insecticidal [ 4 ], antibacterial [ 5 , 6 ], anticonvulsant [ 7 ], antioxidant [ 8 ], herbicidal [ 9 ] agents, as well as adenosine receptors [ 10 ] or HIF prolyl hydrolase [ 11 ] and myeloperoxidase [ 12 ] inhibitors. On the other hand, pyridotriazine derivatives were discovered as prospective drugs showing antithrombotic [ 13 ], antimicrobial [ 14 , 15 ], antifungal [ 16 ] and anti-Alzheimer disease [ 17 ] effects. They are also antagonists of serotonin receptors [ 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

The Structural and Optical Properties of 1,2,4-Triazolo[4,3-a]pyridine-3-amine

et al. 2022

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The structural and spectroscopic properties of a new triazolopyridine derivative (1,2,4-triazolo[4,3-a]pyridin-3-amine) are described in this paper. Its FTIR spectrum was recorded in the 100–4000 cm−1 range and its FT-Raman spectrum in the range 80–4000 cm−1. The molecular structure and vibrational spectra were analyzed using the B3LYP/6-311G(2d,2p) approach and the GAUSSIAN 16W program. The assignment of the observed bands to the respective normal modes was proposed on the basis of PED calculations. XRD studies revealed that the studied compound crystallizes in the centrosymmetric monoclinic space group P21/n with eight molecules per unit cell. However, the asymmetric unit contains two 1,2,4-triazolo[4,3-a]pyridin-3-amine molecules linked via N‒H∙∙∙N hydrogen bonds with a R22(8) graph. The stability of the studied molecule was considered using NBO analysis. Electron absorption and the luminescence spectra were measured and discussed in terms of the calculated singlet, triplet, HOMO and LUMO electron energies. The Stokes shifts derived from the optical spectra were equal to 9410 cm−1 for the triazole ring and 7625 cm−1 for the pyridine ring.

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Synthesis, Molecular Docking and in Vitro Screening of Some Newly Synthesized Triazolopyridine, Pyridotriazine and Pyridine–Pyrazole Hybrid Derivatives

Cited by 30 publications

References 58 publications

Development of a Novel Series of Anticancer and Antidiabetic: Spirothiazolidines Analogs

Development of a Novel Series of Anticancer and Antidiabetic: Spirothiazolidines Analogs

Synthesis, antibacterial, anti-oxidant and molecular docking studies of imidazoquinolines

The Structural and Optical Properties of 1,2,4-Triazolo[4,3-a]pyridine-3-amine

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