Antiviral activity of thiadiazoles, oxadiazoles, triazoles and thiazoles

Tawfik, Samar S.; Liu, Mengyao; Farahat, Abdelbasset A.

doi:10.24820/ark.5550190.p011.308

Cited by 16 publications

(7 citation statements)

References 100 publications

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“…The electrophilic addition of halogens to cyclic enol ethers has been investigated earlier by Lemieux and Fraser-Reid [ 39 ], who proposed a general mechanism involving the initial formation of carbenium ions which, upon nucleophilic attack by halide ion, give mainly the products of thermodynamic control. Later on, it has been shown that the product formation is under kinetic control and that the stereoselectivity depends on the solvent polarity [ 7 , 9 , 10 ], the structure of the enol ether, and the nature of the halogen [ 16 , 40 , 41 , 42 ].…”

Section: Resultsmentioning

confidence: 99%

“…1,3,4-Thiadiazole represents an important heterocyclic scaffold due to its pharmacological activity. Their derivatives exhibit various and significant activities such as antibacterial [ 1 ], antifungal, anti-inflammatory [ 2 ], anti-tuberculosis [ 3 ], antidepressant [ 4 ], and anticancer [ 5 , 6 , 7 ] activities, etc. The 1,3,4-Thiadiazole ring influences cancer cell lines mainly due to ability of nitrogen atoms to donate electrons and form hydrogen bonds or chelate certain metal ions [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Preliminary Anticancer Activity Assessment of N-Glycosides of 2-Amino-1,3,4-thiadiazoles

et al. 2021

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The addition of 2-amino-1,3,4-thiadiazole derivatives with parallel iodination of differently protected glycals has been achieved using a double molar excess of molecular iodine under mild conditions. The corresponding thiadiazole derivatives of N-glycosides were obtained in good yields and anomeric selectivity. The usage of iodine as a catalyst makes this method easy, inexpensive, and successfully useable in reactions with sugars. Thiadiazole derivatives were tested in a panel of three tumor cell lines, MCF-7, HCT116, and HeLa. These compounds initiated biological response in investigated tumor models in a different rate. The MCF-7 is resistant to the tested compounds, and the cytometry assay indicated low increase in cell numbers in the sub- G1 phase. The most sensitive are HCT-116 and HeLa cells. The thiadiazole derivatives have a pro-apoptotic effect on HCT-116 cells. In the case of the HeLa cells, an increase in the number of cells in the sub-G1- phase and the induction of apoptosis was observed.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Preliminary Anticancer Activity Assessment of N-Glycosides of 2-Amino-1,3,4-thiadiazoles

et al. 2021

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“…By applying microwave technology, different oxadiazole derivatives can be synthesized and also screened to find out new therapeutic molecules with diverse biological activities such as antibacterial, antifungal, antidepressant, antitubercular and antiinflammatory, etc. [ 71 , 72 , 73 , 74 ]. Hence, oxadiazole is considered a significant heterocyclic core and becomes a major scaffold for the development of new drug candidates because of its potential to be involved in the binding interactions with different targets or receptors with suitable metabolic profile [ 75 , 76 , 77 , 78 ].…”

Section: Future Developmentmentioning

confidence: 99%

Green Synthetic Approach: An Efficient Eco-Friendly Tool for Synthesis of Biologically Active Oxadiazole Derivatives

et al. 2021

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Green synthetic protocol refers to the development of processes for the sustainable production of chemicals and materials. For the synthesis of various biologically active compounds, energy-efficient and environmentally benign processes are applied, such as microwave irradiation technology, ultrasound-mediated synthesis, photo-catalysis (ultraviolet, visible and infrared irradiation), molecular sieving, grinding and milling techniques, etc. Thesemethods are considered sustainable technology and become valuable green protocol to synthesize new drug molecules as theyprovidenumerous benefits over conventional synthetic methods.Based on this concept, oxadiazole derivatives are synthesized under microwave irradiation technique to reduce the formation of byproduct so that the product yield can be increased quantitatively in less reaction time. Hence, the synthesis of drug molecules under microwave irradiation follows a green chemistry approach that employs a set of principles to minimize or remove the utilization and production of hazardous toxic materials during the design, manufacture and application of chemical substances.This approach plays a major role in controlling environmental pollution by utilizing safer solvents, catalysts, suitable reaction conditions and thereby increases the atom economy and energy efficiency. Oxadiazole is a five-membered heterocyclic compound that possesses one oxygen and two nitrogen atoms in the ring system.Oxadiazole moiety is drawing considerable interest for the development of new drug candidates with potential therapeutic activities including antibacterial, antifungal, antiviral, anticonvulsant, anticancer, antimalarial, antitubercular, anti-asthmatic, antidepressant, antidiabetic, antioxidant, antiparkinsonian, analgesic and antiinflammatory, etc. This review focuses on different synthetic approaches of oxadiazole derivatives under microwave heating method and study of their various biological activities.

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“…Heterocyclic compounds specially the five membered (thiazoles, thiadiazoles, triazoles, 1,3,4-oxadiazoles and benzimidazole ring) have shown a very interesting biological activity [ 8 ]. These compounds also showed very promising antiviral activity against different viruses [ 9 ]. Triazole based derivatives has been attracting the researcher's attention due to its effectiveness as therapeutic drugs in the field of antibacterial, antiviral, antifungal, antitumor and antihypertensive agents.…”

Section: Introductionmentioning

confidence: 99%

Anti-COVID-19 activity of some benzofused 1,2,3-triazolesulfonamide hybrids using in silico and in vitro analyses

Shaaban

Elwakil

Hamed

et al. 2021

Chemometrics and Intelligent Laboratory Systems

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Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is a pandemic fatal infection with no known treatment. The severity of the disease and the fast viral mutations forced the scientific community to search for potential solution. Here in the present manuscript, some benzofused1,2,3triazolesulfonamide hybrids were synthesized and evaluated for their anti- SARS-CoV-2 activity using in silico prediction then the most potent compounds were assessed using in-Vitro analysis. The in-Silico study was assessed against RNA dependent RNA polymerase, Spike protein S1, Main protease (3CLpro) and 2'-O-methyltransferase (nsp16). It was found that 4b and 4c showed high binding scores against RNA dependent RNA polymerase reached -8.40 and -8.75 Kcal/mol, respectively compared to the approved antiviral (remdesivir -6.77 Kcal/mol). Upon testing the binding score with SARS-CoV-2 Spike protein it was revealed that 4c exhibited the highest score (-7.22 Kcal/mol) compared to the reference antibacterial drug Ceftazidime (-6.36 Kcal/mol). Surprisingly, the two compounds 4b and 4c showed the highest binding scores against SARS-CoV-2 3CLpro (-8.75, -8.48 Kcal/mol, respectively) and nsp16 (- 8.84 and – 8.89 Kcal/mol, respectively) displaying many types of interaction with all the enzymes binding sites. The derivatives 4b and 4c were examined in vitro for their potential anti-SARS-CoV-2 and it was revealed that 4c was the most promising compound with IC50 reached 758.8108 mM and complete (100%) inhibition of the binding of SARS-CoV-2 virus to human ACE2 can be accomplished by using 0.01 mg.

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Antiviral activity of thiadiazoles, oxadiazoles, triazoles and thiazoles

Cited by 16 publications

References 100 publications

Synthesis and Preliminary Anticancer Activity Assessment of N-Glycosides of 2-Amino-1,3,4-thiadiazoles

Synthesis and Preliminary Anticancer Activity Assessment of N-Glycosides of 2-Amino-1,3,4-thiadiazoles

Green Synthetic Approach: An Efficient Eco-Friendly Tool for Synthesis of Biologically Active Oxadiazole Derivatives

Anti-COVID-19 activity of some benzofused 1,2,3-triazolesulfonamide hybrids using in silico and in vitro analyses

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