Synthesis of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles starting from 5-nitro-2-furoic acid and evaluation of their antimicrobial activity

Badr, Sahar; Barwa, Rasha

doi:10.1016/j.bmc.2011.06.024

Cited by 70 publications

(16 citation statements)

References 34 publications

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“…[25] A class of 4-amino-1,2,4-triazole-3-thiols and structurally related analogues were identified and developed as A3G inhibitors based on MLS-0036803, a HTS hit renamed MN256.0105 ( 1 ) in-house. Scaffolds identical or analogous to 1 have been previously investigated for fungicidal, [26] antioxidant, [27] cytotoxic, [28] antimicrobial [28] and anti-osteoarthritic [29] applications.…”

Section: Introductionmentioning

confidence: 99%

Small‐Molecule APOBEC3G DNA Cytosine Deaminase Inhibitors Based on a 4‐Amino‐1,2,4‐triazole‐3‐thiol Scaffold

Olson

Harris

et al. 2012

ChemMedChem

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APOBEC3G (A3G) is a single-stranded DNA cytosine deaminase that functions in innate immunity against retroviruses and retrotransposons. Although A3G can potently restrict Vif-deficient HIV-1 replication by catalyzing excessive levels of G-to-A hypermutation, sublethal levels of A3G-catalyzed mutation may contribute to the high level of HIV-1 fitness and its incurable prognosis. To chemically modulate A3G catalytic activity with the goal of reducing the HIV-1 genomic mutation rate, we synthesized and biochemically evaluated a class of 4-amino-1,2,4-triazole-3-thiol small molecule inhibitors that were identified by high-throughput screening. This class of compounds exhibits low micromolar (3.9 – 8.2 µm) inhibitory potency and remarkable specificity for A3G versus related deaminase APOBEC3A. Chemical modifications to inhibitors, A3G mutational screening, and thiol reactivity studies implicate C321, a residue proximal to the active site, as the critical A3G target for this class of molecules.

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Section: Introductionmentioning

confidence: 99%

Small‐Molecule APOBEC3G DNA Cytosine Deaminase Inhibitors Based on a 4‐Amino‐1,2,4‐triazole‐3‐thiol Scaffold

Olson

Harris

et al. 2012

ChemMedChem

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“…25 In recent years, these scaffolds have attracted attention because of their cytotoxic effects. [26][27][28][29][30][31][32][33] This considerable background has directed us to investigate the anticancer effect of our compounds bearing a triazolothiadiazine core. 34 The encouraging results we obtained, and the impressive history of NSAIDs in the cancer research field, have inspired us to design new hybrid compounds by combining a 1,2,4-triazolo [3,4- In this study the bioactivities of novel triazolothiadiazines were tested initially on epithelial cancer cells, then the mechanism of action was examined with liver cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Novel triazolothiadiazines act as potent anticancer agents in liver cancer cells through Akt and ASK-1 proteins

Aytac

Durmaz

Houston

et al. 2016

Bioorganic & Medicinal Chemistry

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Newly designed triazolothiadiazines incorporating with structural motifs of nonsteroidal analgesic anti-inflammatory drugs were synthesized and screened for their bioactivity against epithelial cancer cells. Compounds with bioactivities less then ∼5μM (IC50) were further analyzed and showed to induce apoptotic cell death and SubG1 cell cycle arrest in liver cancer cells. Among this group, two compounds (1g and 1h) were then studied to identify the mechanism of action. These molecules triggered oxidative stress induced apoptosis through ASK-1 protein activation and Akt protein inhibition as demonstrated by downstream targets such as GSK3β, β-catenin and cyclin D1. QSAR and molecular docking models provide insight into the mechanism of inhibition and indicate the optimal direction of future synthetic efforts. Furthermore, molecular docking results were confirmed with in vitro COX bioactivity studies. This study demonstrates that the novel triazolothiadiazine derivatives are promising drug candidates for epithelial cancers, especially liver cancer.

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“…Furthermore, biheterocyclic compounds bearing a triazole moiety and another heterocyclic moiety combined in one molecular union are also eminent to possess broad spectrum of biological activities, one such imperative being triazolo thiadiazine derivatives [2]. Substituted 1,2,4-triazolo-1,3,4-thiadiazines are reported to possess antifungal, antibacterial, and anticancer activities [3–6]. Additional bioactivity shown by such molecules includes antitubercular, anti-inflammatory, and antimolluscicidal [7, 8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Some Novel 5-[(3-Aralkyl Amido/Imidoalkyl) Phenyl]-1,2,4-Triazolo[3,4-b]-1,3,4-Thiadiazines as Antiviral Agents

Pandey

Tusi

et al. 2012

ISRN Organic Chemistry

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A series of novel 4-amino-5-mercapto-3-[(3-aralkyl amido/imidoalkyl) phenyl]-1,2,4-triazoles (5a-d) were obtained by treating m-(aralkyl amido/imidoalkyl) benzoic acid hydrazides (3a-d) with carbon disulphide in alcoholic KOH and hydrazine hydrate, respectively. These triazole derivatives were employed in the synthesis of 5-[(3′-aralkyl amido/imidoalkyl) phenyl]-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (6a-d). The newly synthesized compounds were evaluated for their antiviral activity against two animal viruses, namely, Japanese encephalitis virus (JEV) strain P20778 and herpes simplex virus-1 (HSV-1) strain 753166.

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Synthesis of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles starting from 5-nitro-2-furoic acid and evaluation of their antimicrobial activity

Cited by 70 publications

References 34 publications

Small‐Molecule APOBEC3G DNA Cytosine Deaminase Inhibitors Based on a 4‐Amino‐1,2,4‐triazole‐3‐thiol Scaffold

Small‐Molecule APOBEC3G DNA Cytosine Deaminase Inhibitors Based on a 4‐Amino‐1,2,4‐triazole‐3‐thiol Scaffold

Novel triazolothiadiazines act as potent anticancer agents in liver cancer cells through Akt and ASK-1 proteins

Synthesis and Biological Evaluation of Some Novel 5-[(3-Aralkyl Amido/Imidoalkyl) Phenyl]-1,2,4-Triazolo[3,4-b]-1,3,4-Thiadiazines as Antiviral Agents

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