Design, synthesis and biological activities of novel 1,2,3-thiadiazole derivatives containing oxime ether

Background: Oxime compounds, including oxime ethers and oxime esters, possess various biological activities. Many oxime ethers have been widely used in the fields of pesticides and medicines. However, oxime ethers are rarely used in the field of pesticides. Methods: We chose the excellent fungicide pyrifenox as the lead compound, integrated pyridinyl, adamantyl and benzoyl moieties into one molecule, while also designed and synthesized ten 1- (adamantan-1-yl)ethanone oxime esters containing pyridinyl moiety. Moreover, we also evaluated their preliminary antifungal activities against S. sclerotiorum and B. cinerea. Results: The target compounds were characterized by NMR, IR and HRMS. The preliminary bioactivity test showed that they exhibited some antifungal activity to S. sclerotiorum and B. cinerea, and EC50 values were in the range of 14.16-32.97 and 27.60-52.82 μg/mL, respectively. Conclusion: Some target compounds such as 3d, 3e, 3h and 3i, exhibited moderate activities against S. sclerotiorum, with EC50 values of 14.16-18.18 μg/mL.

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Design, Synthesis, Anti-Proliferative Evaluation and Cell Cycle Analysis of Hybrid 2-Quinolones

Anti-Cancer Agents in Medicinal Chemistry ◽

10.2174/1871520619666190319142934 ◽

2019 ◽

Vol 19 (9) ◽

pp. 1132-1140

Author(s):

Heba A.E. Mohamed ◽

Hossa F. Al-Shareef

Keyword(s):

Cell Cycle ◽

Anticancer Agents ◽

Biological Activities ◽

Flow Cytometric Analysis ◽

Annexin V ◽

Cytotoxic Activities ◽

Significant Group ◽

Design Synthesis ◽

Standard Drug ◽

Wide Range

Background: Quinolones are a significant group of nitrogen heterocyclic compounds that exist in therapeutic agents, alkaloids, and synthetic small molecules that have important biological activities. A wide range of quinolones have been used as antituberculosis, antibacterial, anti-malarial, antifungal, anticonvulsant, anticancer agents and urease inhibitors. Methods: Ethyl 3,3-disubstituted-2-cyano propionates containing hybride quinolones derivatives were synthesized by the reaction of 1-amino-7-hydroxy-4-methylquinolin-2(1H)-one and its dibromo derivative with α, β-unsaturated carbonyl in ethanol. Results: A novel series of hybrid 2-quinolone derivatives was designed and synthesized. The compounds structures were confirmed using different spectroscopic methods and elemental analysis. The cytotoxic activities of all the compounds were assessed against HepG2 cell line in comparison with doxorubicin as a standard drug. Conclusion: Most compounds revealed superior anti-proliferative activity than the standard. Compound 4b, is the most active compound (IC50 = 0.39mM) compared with doxorubicin (IC50 = 9.23mM). DNA flow cytometric analysis of compound 4b showed cell cycle arrest at G2/M phase with a concomitant increase of cells in apoptotic phase. Dual annexin-V/ propidium iodide staining assay of compound 4b revealed that the selected candidate increased the apoptosis of HepG-2 cells more than control.

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Design, synthesis, and bioactivity evaluation of novel thiochromanone derivatives containing an oxime or oxime ether moiety

Journal of Heterocyclic Chemistry ◽

10.1002/jhet.4338 ◽

2021 ◽

Author(s):

Lu Yu ◽

Lingling Xiao ◽

Jiyan Chi ◽

Zhangfei Tang ◽

Jie Li ◽

...

Keyword(s):

Oxime Ether ◽

Design Synthesis

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Development of adamantane scaffold containing 1,3,4-thiadiazole derivatives: design, synthesis, anti-proliferative activity and molecular docking study targeting EGFR

Bioorganic Chemistry ◽

10.1016/j.bioorg.2021.104794 ◽

2021 ◽

pp. 104794

Author(s):

Mohammed M. S. Wassel ◽

Yousry A. Ammar ◽

Gameel A. M. Elhag Ali ◽

Amany Belal ◽

Ahmed B. M. Mehany ◽

...

Keyword(s):

Molecular Docking ◽

Proliferative Activity ◽

Docking Study ◽

Molecular Docking Study ◽

Design Synthesis ◽

Thiadiazole Derivatives

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Synthesis and characterization of a new series of thiadiazole derivatives as potential anticancer agents

Heterocyclic Communications ◽

10.1515/hc-2020-0002 ◽

2020 ◽

Vol 26 (1) ◽

pp. 6-13 ◽

Cited By ~ 1

Author(s):

Ulviye Acar Çevik ◽

Derya Osmaniye ◽

Serkan Levent ◽

Begüm Nurpelin Sağlik ◽

Betül Kaya Çavuşoğlu ◽

...

Keyword(s):

Anticancer Agents ◽

Biological Activities ◽

Cancer Cell Line ◽

Chemotherapeutic Agents ◽

Anticancer Activities ◽

Normal Tissues ◽

H Nmr ◽

Wide Range ◽

Thiadiazole Derivatives ◽

Low Efficiency

AbstractCancer is one of the most common causes of death in the world. Despite the importance of combating cancer in healthcare systems and research centers, toxicity in normal tissues and the low efficiency of anticancer drugs are major problems in chemotherapy. Nowadays the aim of many medical research projects is to discover new safer and more effective anticancer agents. 1,3,4-Thiadiazole compounds are important fragments in medicinal chemistry because of their wide range of biological activities, including anticancer activities. The aim of this study was to determine the capacity of newly synthesized 1,3,4-thiadiazole compounds as chemotherapeutic agents. The structures of the obtained compounds were elucidated using 1H-NMR, 13C-NMR and mass spectrometry. Although the thiadiazole derivatives did not prove to be significantly cytotoxic to the tumour tissue cultures, compound 4i showed activity against the C6 rat brain cancer cell line (IC50 0.097 mM) at the tested concentrations.

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Functional design of glycan-conjugated molecules using a chemoenzymatic approach

Bioscience Biotechnology and Biochemistry ◽

10.1093/bbb/zbab024 ◽

2021 ◽

Author(s):

Makoto Ogata

Keyword(s):

Molecular Weight ◽

Large Scale ◽

Biological Activities ◽

Natural Compounds ◽

Low Molecular Weight ◽

Functional Design ◽

Enzymatic Method ◽

Conjugated Molecules ◽

Design Synthesis ◽

And Function

Abstract Carbohydrates play important and diverse roles in the fundamental processes of life. We have established a method for accurately and a large scale synthesis of functional carbohydrates with diverse properties using a unique enzymatic method. Furthermore, various artificial glycan-conjugated molecules have been developed by adding these synthetic carbohydrates to macromolecules and to middle and low molecular weight molecules with different properties. These glycan-conjugated molecules have biological activities comparable to or higher than those of natural compounds, and present unique functions. In this review, several synthetic glycan-conjugated molecules are taken as examples to show design, synthesis and function.

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