Novel scaffold hopping of potent benzothiazole and isatin analogues linked to 1,2,3-triazole fragment that mimic quinazoline epidermal growth factor receptor inhibitors: Synthesis, antitumor and mechanistic analyses

Rezki, Nadjet; Almehmadi, Meshal A.; Ihmaid, Saleh; Shehata, Ahmed; Omar, Abdelsattar M.; Ahmed, Hany E. A.; Aouad, Mohamed Reda

doi:10.1016/j.bioorg.2020.104133

Cited by 64 publications

(45 citation statements)

References 57 publications

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“…Azzam et al [ 39 ] proved the antiviral effect of some (3-benzo- [d]thiazole-2-yl)-2-pyridonesagainst both DNA viruses (herpes simplex virus type 1 (HSV-1)) and adenovirus type 7 (HAdV7) in addition to RNA viruses (coxsackie virus B4 (CBV4), hepatitis A virus (HAV) HM175, and HCVcc genotype). The in silico toxicity of the compounds 4b and 4c were reported in our previous procedure [ 12 , 13 ] which predicted that both compounds were non-carcinogenic. Further acute toxicity study using in vivo analysis was performed [ 12 , 13 ] and LD 50 in rat was proved to be 2.29–2.41 mol/kg.…”

Section: Resultsmentioning

confidence: 99%

“…The in silico toxicity of the compounds 4b and 4c were reported in our previous procedure [ 12 , 13 ] which predicted that both compounds were non-carcinogenic. Further acute toxicity study using in vivo analysis was performed [ 12 , 13 ] and LD 50 in rat was proved to be 2.29–2.41 mol/kg.…”

Section: Resultsmentioning

confidence: 99%

“…In the present study, we have reproduced the synthesis of some novel 1,2,3-triazole-sulfa drug hybrids carrying different heterocyclic entities, including benzothiazole, isatin and/or benzimidazole core according to our reported procedure [ 12 , 13 ] ( Scheme 1 ). The synthetic methodology adopted required Cu(I)-catalyzed click 1,3-dipolar cycloaddition reaction between the appropriate heterocyclic akynes 1a-c with a variety of sulfa drug azides 2a-e in the presence of CuSO 4 and sodium ascorbate as catalysts.…”

Section: Methodsmentioning

confidence: 99%

“…The study includes also the synthesis of bis-(1,2,3-triazole-sulfa-drug) benzimidazole hybrids 4a-c , through the coupling of the bis-propargylated benzimidazole with the appropriate sulfa drug azides in 1:2 ratio, under the same optimized Cu(I)-click conditions. Full characterization of the newly designed 1,2,3-triazole hybrids has been reported in detail in our previously reported works [ 12 , 13 ].…”

Section: Methodsmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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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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“…Triazole and thiadiazole rings are known to be included in the structure of various drugs [3,4]. From these classes of heterocyclic compounds, the synthesis of novel derivatives of 1,2,4-triazole-3-thionate and 2-amino-1,3,4thiazole has attracted great interest due to various biological properties such as antibacterial [5,6], antifungal [7], antituberculosis [8,9], interferon [10], antioxidant [11], antitumor [12], anti-inflammatory [13,14], and anticonvulsant [15]. e thermogravimetry analysis technique is employed to identify the acceptability level regarding the coordination nature in between the central metal ions and different kinds of interesting biomolecule chelates, such as amino acids [16], caffeine molecule [17], or chemical materials that have a biological behavior as ethylene-and propylene-urea as well as ethylene-thiourea [18].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Thermogravimetric and Antimicrobial Investigation of Cd (II) and Sn (II) Adducts of Mercaptopyridine, Amino Triazole Derivatives, and Mercaptothiazoline Organic Ligand Moieties

Gaber

Alsanie

Farias

et al. 2021

Bioinorganic Chemistry and Applications

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The solid adducts of SnCl2.(3amt).H2O, SnCl2.2(3amt).H2O, CdCl2.(3amt), CdCl2.2(3amt), SnCl2.(2mct).0.5H2O, SnCl2.2(2mct), CdCl2.(2mct), CdCl2.2(2mct).H2O, SnCl2.(2mcp).1.5H2O, >2.2(2mcp).4H2O, CdCl2.(2mcp), CdCl2.2(2mcp), SnCl2.(4amt).4H2O, SnCl2.2(4amt).1.5H2O, CdCl2.(4amt).H2O, and CdCl2.2(4amt) (where the 3amt, 4amt, 2mct, and 2mcp represent 3-amino-1,2,4-triazole, 4-amino-1,2,4-triazole, 2-mercaptothiazoline, and 2-mercaptopyridine simple organic chelates, respectively) were prepared using a solid-state route and investigated by CHN elemental analysis and infrared spectroscopy. Additionally, we investigated the thermogravimetric characterization and antimicrobial proprieties. It is verified that for 3amt and 4amt adducts, the coordination occurs through nitrogen atom. For 2mct compounds, the coordination occurs through nitrogen (Sn) or sulfur (Cd). For 2mcp adducts, both coordination sites nitrogen and sulfur are involved. By examination of TG curves, it is confirmed that for each hydrated compounds, the first mass loss step is linked with the release of water molecules followed by the release of ligand molecules and sublimation of the metal chloride. Furthermore, it is verified that, considering only the release of ligand molecules (3amp, 4amp, 2mct, or 2mcp), the cadmium adducts are always more stable than the correspondent tin adducts probably due to the formation of cross-linking bonds in these compounds. Finally, of these 16 adducts, 14 showed antimicrobial activities against different bacterial and fungal strains.

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1,2,3‐Triazole hybrids as anticancer agents: A review

Alam

2021

Archiv der Pharmazie

155

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Despite the advancements in the development of anticancer agents, more effective and safer anticancer drugs still need to be developed as the current agents cause unwanted side effects and many patients have become drug resistant. 1,2,3-Triazoles, due to their remarkable biological potential, have received considerable attention in drug discovery for the development of anticancer agents. The present review article presents an overview of the recent advances in 1,2,3-triazole hybrids with anticancer potential over the last 2 years, their chemical structures, structure-activity relationships, and mechanisms of action, as well as insights into the docking studies.

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Novel scaffold hopping of potent benzothiazole and isatin analogues linked to 1,2,3-triazole fragment that mimic quinazoline epidermal growth factor receptor inhibitors: Synthesis, antitumor and mechanistic analyses

Cited by 64 publications

References 57 publications

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

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

Preparation and Thermogravimetric and Antimicrobial Investigation of Cd (II) and Sn (II) Adducts of Mercaptopyridine, Amino Triazole Derivatives, and Mercaptothiazoline Organic Ligand Moieties

1,2,3‐Triazole hybrids as anticancer agents: A review

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