Synthesis of New 2,4‐Diaryl‐6‐methyl‐5‐nitropyrimidines as Antibacterial and Antioxidant Agents

A new series of 2,4‐diaryl‐6‐methyl‐5‐nitropyrimidines ( 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h , 5i ) were synthesized in good yields by Suzuki–Miyaura coupling of 2,4‐dichloro‐6‐methyl‐5‐nitropyrimidine ( 3 ) with various aryl boronic esters ( 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4h , 4i ) in the presence of 1,1′‐ bis(diphenylphosphino)ferrocene dichloropalladium(II) (Pd(dppf)₂Cl₂). Further, antibacterial and antioxidant properties were screened for the title compounds 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h , 5i . Most of the compounds possessed significant activity against Gram‐positive bacteria Staphylococcus aureus and Bacillus subtilis and Gram‐negative bacteria Escherichia coli and Klebsiella pneumoniae. The antioxidant activity of the title compounds showed significant antioxidant activity when compared with vitamin C.     

Easy Access to α-Bromoketones and Epoxides from vic-Dibromides Under Aqueous Conditions

The conversion of vic-1,2 dibromides to α-bromoketones and epoxides using H₂O₂/dioxane and NaOH/water respectively under mild conditions has been described.     

Green Oxidation of Methylarenes to Benzoic Acids with Bromide/Bromate in Water

An efficient and convenient procedure has been developed for the oxidation of methylarenes to the corresponding benzoic acids using a bromide/bromate-based reagent system in water. Regeneration and reusability of the bromide/bromate reagent is demonstrated.     

Isolation and biological evaluation of chromone alkaloid dysoline,a new regioisomer of rohitukine from Dysoxylum binectariferum

The chromone alkaloid dysoline (1), a new regioisomer of rohitukine (2) along with rohitukine and rohitukine-N-oxide (3) were isolated from the stem barks of Dysoxylum binectariferum. The structure of dysoline (1) was determined by extensive 2D-NMR studies and the absolute configuration was established by NOESY and CD spectra. Dysoline (1) consisted of a 5,7-dihydroxy-2-methylchromone nucleus substituted with a 2′-hydroxylated N-Me piperidine ring at the C-6 position. Dysoline differs from rohitukine by the position of the piperidine ring on the chromone nucleus. Dysoline displayed promising cytotoxicity in HT1080 fibrosarcoma cells with an IC₅₀ of 0.21 μM, and also displayed significant inhibition of proinflammatory cytokines TNF-α and IL-6.     

Simultaneous high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS-MS) analysis of cyanide and thiocyanate from swine plasma

An analytical procedure for the simultaneous determination of cyanide and thiocyanate in swine plasma was developed and validated. Cyanide and thiocyanate were simultaneously analyzed by high-performance liquid chromatography tandem mass spectrometry in negative ionization mode after rapid and simple sample preparation. Isotopically labeled internal standards, Na¹³C¹⁵N and NaS¹³C¹⁵N, were mixed with swine plasma (spiked and nonspiked), proteins were precipitated with acetone, the samples were centrifuged, and the supernatant was removed and dried. The dried samples were reconstituted in 10 mM ammonium formate. Cyanide was reacted with naphthalene-2,3-dicarboxaldehyde and taurine to form N-substituted 1-cyano[f]benzoisoindole, while thiocyanate was chemically modified with monobromobimane to form an SCN-bimane product. The method produced dynamic ranges of 0.1–50 and 0.2–50 μM for cyanide and thiocyanate, respectively, with limits of detection of 10 nM for cyanide and 50 nM for thiocyanate. For quality control standards, the precision, as measured by percent relative standard deviation, was below 8 %, and the accuracy was within ±10 % of the nominal concentration. Following validation, the analytical procedure successfully detected cyanide and thiocyanate simultaneously from the plasma of cyanide-exposed swine.     

Identification of HPr kinase/phosphorylase inhibitors: novel antimicrobials against resistant Enterococcus faecalis

Journal of Computer-Aided Molecular Design - Enterococcus faecalis, a gram-positive bacterium, is among the most common nosocomial pathogens due to its limited susceptibility to antibiotics and its...     

Mesoionic Dithiolates (MIDts) Derived from 1,3-Imidazole-Based Anionic Dicarbenes (ADCs)

Mesoionic dithiolates [(MIDt^Ar)Li(LiBr)₂(THF)₃] (MIDt^Ar={SC(NDipp)}₂CAr; Dipp=2,6-iPr₂C₆H₃; Ar=Ph 3 a , 3-MeC₆H₄ (3-Tol) 3 b , 4-Me₂NC₆H₄ (DMP) 3 c ) and [(MIDt^Ph)Li(THF)₂] ( 4 ) are readily accessible (in≥90 % yields) as crystalline solids on treatments of anionic dicarbenes Li(ADC^Ar) ( 2 a - c ) (ADC^Ar={C(NDipp)₂}₂CAr) with elemental sulfur. 3 a - c and 4 are monoanionic ditopic ligands with both the sulfur atoms formally negatively charged, while the 1,3-imidazole unit bears a formal positive charge. Treatment of 4 with (L)GeCl₂ (L=1,4-dioxane) affords the germylene (MIDt^Ph)GeCl ( 5 ) featuring a three-coordinated Ge atom. 5 reacts with (L)GeCl₂ to give the Ge−Ge catenation product (MIDt^Ph)GeGeCl₃ ( 6 ). KC₈ reduction of 5 yields the homoleptic germylene (MIDt^Ph)₂Ge ( 7 ). Compounds 3 a - c and 4 – 7 have been characterized by spectroscopic studies and single-crystal X-ray diffraction. The electronic structures of 4 – 7 have been analyzed by DFT calculations.     

Convenient Microwave-Assisted Chlorosulfonic Acid-Catalyzed Synthesis of Some Quinazolinones from 2-Phenylindole

Russian Journal of Organic Chemistry - A new convenient method has been developed for the synthesis of quinazolinones from 2-phenyl-1H-indole and substituted amines under catalysis by...     

Identification and quantification of anthocyanins,flavonoids, and phenolic acids in flowers of Rhododendron arboreum and evaluation of their antioxidant potential

The current study aimed to investigate the anthocyanins, non-anthocyanins (flavonoids and phenolic acids), and free radicals scavenging potential in the flowers of Rhododendron arboreum using ultra high performance liquid chromatography with ion mobility quadrupole time of flight tandem mass spectrometry. A total of 25 constituents including nine anthocyanins, six phenolic acids, and ten flavonoids were identified in the flower extract. The major anthocyanins identified were cyanidin-3-O-β-galactoside ( 1 ), cyanidin-3-O-α-arabinoside ( 4 ), and cyanidin-3-O-rhamnoside ( 8 ), while quercetin glycosides were the main identified flavonoids in R. arboreum flowers. Additionally, ultra high performance liquid chromatography methods were developed and validated for the quantification of nine compounds (anthocyanins, flavonoid glycosides, and phenolic acids); five of them were quantified using internal standards. The extracts were analyzed for total phenolics (123.6 mg GAE/g), anthocyanin content (1.76% w/w), and evaluated for antioxidant properties against 2,2-diphenyl-1-picrylhydrazyl radical (IC₅₀: 102.06 and 96.92 μg/mL) and 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) radical cation (112.25 and 45.59 μM TE/g) assays. The profiling of R. arboreum for anthocyanins is reported for the first time. The findings suggest that the flowers are a promising source of bioactive constituents and could be used as functional food, antioxidants, and nutraceuticals.     

Isolation of a 16π-Electrons 1,4-Diphosphinine-1,4-diide with a Planar C4P2 Ring

Herein, we report the first 1,4-diphosphinine-1,4-diide compound [(ADC^Ph)P]₂ ( 5-Ph ) (ADC^Ph=PhC{(NDipp)C}₂; Dipp=2,6-iPr₂C₆H₃) derived from an anionic dicarbene (ADC^Ph) as a red crystalline solid. Compound 5-Ph containing a 16π-electron planar fused-tricyclic ring system was obtained by the 4e reduction of [(ADC^Ph)PCl₂]₂ ( 4-Ph ) with Mg (or KC₈) in a quantitative yield. Experimental and computational results imply that the central 8π-electrons C₄P₂ ring of 5-Ph , which is fused between two 6π-electrons C₃N₂ aromatic rings, is antiaromatic. Thus, each of the phosphorus atoms of 5-Ph has two electron-lone-pairs, one in a p-type orbital is in conjugation with the C=C bonds of the C₄P₂ ring, while the second resides in a σ-symmetric orbital. This can be shown with the gold complex [(ADC^Ph)P(AuCl)₂]₂ ( 6-Ph ) obtained by reacting 5-Ph with (Me₂S)AuCl. A mixture of 5-Ph and 4-Ph undergoes comproportionation in the presence of MgCl₂ to form the intermediate oxidation state compound [(ADC^Ar)P]₂(MgCl₄) ( 7-Ph ), which is an aromatic species.