2,5-Disubstituted-1,3,4-oxadiazoles: thymidine phosphorylase inhibitors

Khan, Khalid Mohammed; Rani, Mubeen; Ambreen, Nida; Ali, Muhammad; Hussain, Sajjad; Perveen, Shahnaz; Choudhary, M. Iqbal

doi:10.1007/s00044-013-0588-2

Cited by 19 publications

(10 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ferrocenyl bis-chalcone and its cyclized bis-products (1-5) were assayed for their in vitro antibacterial activities by employing disc diffusion test using S. aureus, S. pyogenes, S. typhimurium, and E. coli cultures. Dimethyl sulfoxide (DMSO)-wetted disc and chloramphenicol (30 mg) were used as negative and positive control, respectively [19]. Among all the five tested compounds including chloramphenicol, compound 2 showed better inhibitory effects for both Gram-positive and Gram-negative bacteria.…”

Section: Resultsmentioning

confidence: 99%

“…The crude product thus obtained was filtered, dried, and purified by flash column chromatography (chloroform : methanol; 9:1) to obtain desired products 2, 3, 4, and 5, respectively. Antibacterial activity of the newly synthesized organometallic macromolecules was performed by the disc diffusion method with minor modifications [19]. S. aureus, S. pyogenes, S. typhimurium, and E. coli were subcultured in BHI medium and incubated for 18 h at 37°C, and then the bacterial cells were suspended, according to the McFarland protocol in saline solution to produce a suspension of about 10 À5 CFU/mL: 10 μL of this suspension was mixed with 10 mL of sterile antibiotic agar at 40°C and poured onto an agar plate in a laminar flow cabinet.…”

Section: Moleculementioning

confidence: 99%

See 1 more Smart Citation

Microwave‐assisted Synthesis, Characterization, and Density Functional Theory Study of Biologically Active Ferrocenyl Bis‐pyrazoline and Bis‐pyrimidine as Organometallic Macromolecules

Khan

Asiri

Zayed

et al. 2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Organometallic macromolecules such as ferrocenyl bis‐pyrazoline (2, 3) and bis‐pyrimidine (4, 5) derivatives were synthesized by reacting ferrocenyl bis‐chalcone 1 with thiosemicarbazide/phenylhydrazine/guanidine hydrochloride/thiourea, respectively, under microwave irradiation. Ferrocenyl bis‐chalcone 1 was synthesized by reacting acetyl ferrocene with terephthalaldehyde. Synthesized compounds were characterized by using IR, 1H NMR, 13C NMR, EI‐MS, and elemental analysis. In vitro antibacterial activity against two Gram‐negative and two Gram‐positive bacteria was determined by the disc diffusion assay. Moreover, minimum inhibition concentrations were also measured with reference to chloramphenicol. Thioamide functionally containing ferrocenyl bis‐pyrazoline derivative 2 shows the best antibacterial activity on Escherichia coli and Salmonella typhimurium, among all tested compounds including the reference drug chloramphenicol. The structure–activity relationship is also developed by using computational calculations with density functional theory (DFT)/B3LYP method.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Moleculementioning

confidence: 99%

Microwave‐assisted Synthesis, Characterization, and Density Functional Theory Study of Biologically Active Ferrocenyl Bis‐pyrazoline and Bis‐pyrimidine as Organometallic Macromolecules

Khan

Asiri

Zayed

et al. 2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Thiosemicarbazones are of considerable interest because of their chemistry and potentially beneficial biological activity, such as antibacterial [9], antifungal [10], antiviral [11], ant-amoebic [12], antimalarial, and antitumor activity [13]. Thiosemicarbazones are also used as ligands in the field of inorganic chemistry for the formation of metal complexes due to the presence of thionic sulfur and the azomethine nitrogen [14].…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Synthesis and Spectral Characterization of Biological Activity Heterocyclic Thiosemicarbazone and Its Organometallic Derivatives

Zayed

2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The thiosemicarbazone coordinates to metal through the thionic sulfur and the azomethine nitrogen. The thiosemicarbazone was obtained by the thiosemicarbazide with 3‐acetyl‐2,5‐dimethylfuran by microwave irradiation. Metal complexes were prepared by the reaction of thiosemicarbazone with metal salts. IR, 1H, 13C NMR, FAB‐mass spectroscopic methods, and elemental analysis elucidated the structure of these compounds. The antibacterial activity of these compounds were first tested in vitro by the disk diffusion assay against two Gram‐positive and two Gram‐negative bacteria, and then minimum inhibitory concentration was determined, chloramphenicol as reference drug. The results showed that copper (II) metal complex of the thiosemicarbazone (1.1) is a better inhibitor as compared with chloramphenicol.

show abstract

“…Other dehydrating agents commonly used are CF 3 COOH, H 2 SO 4 , P 2 O 5 , H 3 PO 4 , PCl 5 ( 10 13 ). Literature survey revealed that some oxadiazoles could be directly prepared from carboxylic acids and acylhydrazides in one step which involves longer reaction time and production of by-products ( 13 14 16 ). Another method is reaction of tetrazoles with acyl chlorides in the presence of pyridine ( 12 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial evaluation of some 2,5 disubstituted 1,3,4-oxadiazole derivatives

et al. 2017

View full text Add to dashboard Cite

1,3,4-oxadiazoles are interesting compounds because of their valuable biological effects such as cytotoxic, antibacterial, antifungal, and anti-tubercular activities. Ethyl mandelate was treated with hydrazine hydrate to yield the corresponding acylhydrazide. Some of the 2,5 disubstituted 1,3,4-oxadiazole derivatives were prepared from acylhydrazide using three different procedures. In the first procedure, acylhydrazide was reacted with nitro or chloro aroyle chloride to afford a diacylhydrazide which was cyclized to 2,5-disubstituted 1,3,4-oxadiazole in the presence of phosphoryl chloride as dehydrating agent. In the second procedure, furan-oxadiazole derivative was directly prepared from carboxylic acid and acylhydrazide in one step. In the third procedure, acyl hydrazide was condensed with 5-nitrofuraldehyde to yield 5-nitrofuran-2-yl) methylene)-2-phenyl acetohydrazide intermediate which was cyclized to form the nitrofuran-oxadiazole derivative by acetic anhydride as dehydrating agent. The structures of these compounds have been elucidated by spectral IR and 1H-NMR analysis. All the newly synthesized compounds were screened for their antibacterial and antifungal activities. Compounds F3 and F4 showed remarkable antibacterial activities against Staphylococcus aureus and Escherichia coli bacteria.

show abstract

2,5-Disubstituted-1,3,4-oxadiazoles: thymidine phosphorylase inhibitors

Cited by 19 publications

References 22 publications

Microwave‐assisted Synthesis, Characterization, and Density Functional Theory Study of Biologically Active Ferrocenyl Bis‐pyrazoline and Bis‐pyrimidine as Organometallic Macromolecules

Microwave‐assisted Synthesis, Characterization, and Density Functional Theory Study of Biologically Active Ferrocenyl Bis‐pyrazoline and Bis‐pyrimidine as Organometallic Macromolecules

Microwave‐Assisted Synthesis and Spectral Characterization of Biological Activity Heterocyclic Thiosemicarbazone and Its Organometallic Derivatives

Synthesis and antimicrobial evaluation of some 2,5 disubstituted 1,3,4-oxadiazole derivatives

Contact Info

Product

Resources

About