Synthesis and antiviral activity of 2-substituted methylthio-5-(4-amino-2-methylpyrimidin-5-yl)-1,3,4-oxadiazole derivatives

Wu, Weilong; Chen, Qin; Tai, Anqi; Jiang, Guangqi; Ouyang, Gangfeng

doi:10.1016/j.bmcl.2015.02.069

Cited by 83 publications

(55 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The uorine atoms of the disorderd CF 3 -group were located on a di erence Fourier map and re ned freely. chemistry as pharmacophores or auxophores possessing diverse pharmacological activities, including antibacterial [1][2][3][4][5], anticancer [6][7][8][9][10], antiviral [11][12][13], antihypertensive [14,15], anti-in ammatory [16,17] and antioxidant [18] activities. In addition, some 1,3,4-oxadiazoles are currently used as safe herbicides for crop protection [19][20][21].…”

Section: Methodsmentioning

confidence: 99%

Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C₁₅H₇BrF₆N₂OS₂

Al-Omary

Alanazi

Ghabbour

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

C15H7BrF 6 N 2 OS 2 , monoclinic, P21/c (no. 14), a = 18.8292(14) Å, b = 11.4568(9) Å, c = 8.3400 (6) CCDC no.: 1481834The crystal structure is shown in the gure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of material3,5-Bis(tri uoromethyl)benzyl bromide (614 mg, 2.0 mmol) and anhydrous potassium carbonate (276 mg, 2.0 mmol) were added to a solution of 5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole-2-thiol (526 mg, 2.0 mmol), in N,Ndimethylformamide (5 mL), and the mixture was stirred 87, 121.92, 124.76, 125.75, 130.52, 130.87, 131.51, 132.60, 141.38 Experimental detailsH atoms were placed in calculated positions and were included in the re nement in the riding model approximation. The uorine atoms of the disorderd CF 3 -group were located on a di erence Fourier map and re ned freely. Discussion1,3,4-Oxadiazole derivatives were early identi ed as a structural motif of particular interest in medicinal chemistry, material sciences and agrochemistry. Some 1,3,4-oxadiazoles have occupied a unique situation in the eld of medicinal

show abstract

Section: Methodsmentioning

confidence: 99%

Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C₁₅H₇BrF₆N₂OS₂

Al-Omary

Alanazi

Ghabbour

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

show abstract

“…New 2-substituted methylthio-5-(4-amino-2-methylpyrimidin-5-yl-)-1,3,4-oxadiazole derivatives were designed and produced (Wu et al, 2015a). Six compounds resembled the curative effect of NNM against the virus.…”

Section: Synthetic Productsmentioning

confidence: 99%

Chemical Outbreak for Tobacco Mosaic Virus Control

Luvisi¹,

Panattoni²,

Materazzi³

et al. 2017

IJAB

View full text Add to dashboard Cite

Tobacco mosaic virus (TMV) represents a paradigm in virology, and its control may open the way to effective treatment against phytoviruses. However, the use of chemicals to eliminate the virus from infected plants is very difficult. In this state of the art survey we include trials on a) natural compounds derived from organisms, b) synthetic compounds and c) plant or microorganism extracts, from 2006 to 2015. Plants have been the main source of natural products for anti-TMV tests in the last ten years, and Nicotiana tabacum was the main focus of research, particularly between 2014-2015. Since 2012, there has been a great increase in publications (+45%) and identified compounds (+241%). Between 2012-2015, an average of 31 papers were published and 140 compounds were tested each year, compared to 9 papers and 26 compounds in 2006-2011. Unfortunately, there is little information on the action mechanisms of newly discovered or modified compounds. Cross references to the basic structure of compounds is provided in this review. This chemical outbreak this massive interest in chemical solutions to TMV could be due to the increasing availability of instruments for the analysis of organic compounds. Alternatively Another explanation could be that the chemistry advances in synthesis, which have provided countless drugs with potential benefits for TMV control, have overwhelmed overloaded the plant pathology screening needed to discriminate between compounds and to provide useful agrochemicals for farmers.

show abstract

“…1,3,4‐Oxadiazoles are valuable five‐membered aromatic heterocycles that possess a wide range of biological properties, including antibacterial, antifungal, antiviral, anti‐inflammatory, antiparasitic, and anti‐HIV activities. Some examples of drugs used in clinical medicine, containing the 1,3,4‐oxadiazole unit, are furamizole, which is an antibiotic drug, and raltegravir, an antiretroviral medication used to treat HIV infection (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, antimicrobial evaluation, and molecular docking studies of novel symmetrical 2,5‐difunctionalized 1,3,4‐oxadiazoles

Hkiri

Hafidh

Cavalier

et al. 2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A series of novel symmetrical 2,5‐difunctionalized 1,3,4‐oxadiazole derivatives of pharmacological significance have been synthesized. The obtained compounds were screened for their in vitro antimicrobial activities against Gram‐negative (Escherichia coli and Salmonella typhimurium) and Gram‐positive bacteria (Staphylococcus aureus, Enterococcus faecium, and Streptococcus agalactiae or group B Streptococcus), as well as against the fungus Candida albicans. Although the synthesized compounds showed moderate antifungal activity against C albicans, they exhibited good‐to‐excellent antibacterial activities against several strains, than did standard drugs ampicillin and nystatin. In silico molecular docking in FabI enzyme active site gave information regarding the binding mode of the drug candidate at the molecular level.

show abstract

Synthesis and antiviral activity of 2-substituted methylthio-5-(4-amino-2-methylpyrimidin-5-yl)-1,3,4-oxadiazole derivatives

Cited by 83 publications

References 26 publications

Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C₁₅H₇BrF₆N₂OS₂

Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C₁₅H₇BrF₆N₂OS₂

Chemical Outbreak for Tobacco Mosaic Virus Control

Design, synthesis, antimicrobial evaluation, and molecular docking studies of novel symmetrical 2,5‐difunctionalized 1,3,4‐oxadiazoles

Contact Info

Product

Resources

About

Synthesis and antiviral activity of 2-substituted methylthio-5-(4-amino-2-methylpyrimidin-5-yl)-1,3,4-oxadiazole derivatives

Cited by 83 publications

References 26 publications

Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C15H7BrF6N2OS2

Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C15H7BrF6N2OS2

Chemical Outbreak for Tobacco Mosaic Virus Control

Design, synthesis, antimicrobial evaluation, and molecular docking studies of novel symmetrical 2,5‐difunctionalized 1,3,4‐oxadiazoles

Contact Info

Product

Resources

About

Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C₁₅H₇BrF₆N₂OS₂

Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C₁₅H₇BrF₆N₂OS₂