Synthesis of 2-methoxy-6-(pyrazin-2-ylimino methyl) phenol and its antibacterial activitity (original) (raw)

pyramethamine: Synthesis, characterization, antimicrobial and

2012

Two new mixed ligands metal complexes of sulphadoxine and pyramethamine were prepared by using CuCl 2 .6H 2 O and FeCl 3 .6H 2 O. The complexes were characterized by elemental analysis, melting point determination, molar conductivity, metal content analysis (AAS), IR, magnetic susceptibility measurements and UV-Visible spectroscopy. Based on the analytical and spectroscopic data, the complexes were proposed to have the formulae [M 1 L 1 L 2 (Cl) 2 ] and [M 2 L 1 L 2 (Cl) 3 ] (where M 1 = Cu(II), M 2 = Fe(III)), L 1 = sulphadoxine, L 2 = pyramethamine). The spectroscopic data proposed L 1 to be a monodentate ligand and coordinated through N atom of the NH 2 group in both complexes. Also, L 2 was proposed to be tridentate ligand and coordinated through N atom of the NH 2 groups and through N atom of imine group. However, [M 1 L 1 L 2 (Cl) 2 ] and [M 2 L 1 L 2 (Cl) 3 ] were proposed to possess distorted octahedral geometry. Conductivity measurement values supported the non-electrolytic nature of the complexes. The complexes have been tested in vitro against a number of pathogenic bacteria [g(+) Escherichia coli, g(+) Proteus species, g(+) Pseudomonas aeruginosa and g(+) Salmonella typhi] by using disc diffusion method. Obtained results indicated that the metal complexes exhibited better antibacterial activities as compared to the ligands. Toxicology tests against some tissues of albino rat (Rattus novergicuss) revealed toxicity of the complexes in the kidney as compared to the parent drugs. [M 1 L 1 L 2 (Cl) 2 ] was found to be toxic to the sera, livers and kidneys of the rats used, while [M 2 L 1 L 2 (Cl) 3 ] was found to be non-toxic to the sera, livers and kidneys of the rats as their alkaline phosphatase (ALP) values showed non-significant difference to the control values.

2014 - 3. 2- and 3-substituted imidazolo[1,2-a]pyrazines as inhibitors of bacterial type IV secretion supp info

2014

Page General Chemistry Methods 2 First generation imidazo[1,2-a]pyrazine inhibitors Synthesis of α-azido aryl ketones 16b-e 3 Synthesis of α-azido aryl alcohols 17b-e 6 Synthesis of α-amino aryl alcohols 14b-e 9 Synthesis of 2-[(3-chloropyrazin-2-yl)amino]-1-(2-aryl)ethanols 18b-e 12 Synthesis of 2-[(3-chloropyrazin-2-yl)amino]-1-(2-aryl)ethanones 19b-e 15 Synthesis of 3-aryl-8-chloro-imidazo[1,2-a]pyrazines 20b-e 18 Synthesis of 2-aryl-8-chloro-imidazo[1,2-a]pyrazines 21b-e 22 Synthesis of first generation 2-and 3-substituted 8-aminoimidazo[1,2-a]pyrazines 1 -4, 6 -13 25 Optimisation of reaction conditions for the synthesis of 7 37 Second generation imidazo[1,2-a]pyrazine inhibitors, variants at 8-position, 25 -38 41 Figure S1 HMBC spectrum of 21a 61 Molecular docking -additional information 61 1 H NMR spectra of novel compounds 62 References 121 Details of ATPase assay 123 Figure S1 IC50 curves 125 2-azido-1-(3,4-dimethoxyphenyl)ethanone, 16c 2-Bromo-1-(3,4-dimethoxyphenyl)ethanone 2 (2.33 g, 8.61 mmol) was dissolved in anhydrous DMSO (10 mL) and the mixture was cooled on ice. Sodium azide (671 mg, 10.3 mmol) was added in one portion and the reaction was stirred under argon at RT for 2 h. An immediate colour change of yellow to orange was observed on addition of the sodium azide. The reaction was then quenched with H 2 O (30 mL), and extracted with EtOAc (4 x 40 mL). The combined organic layers were washed with H 2 O (5 x 20 mL) followed by brine (20 mL) and then dried (MgSO 4 ) and filtered. The solvent was removed in vacuo to give an orange solid (1.87 g, 8.46 mmol, 98%) with NMR data comparable with literature values. 3 R f = 0.22 (CH 2 Cl 2 ); IR (ν max /cm -1 , thin film): 2106, 1682, 1595, 1515; 1 H NMR (600 MHz, CDCl 3 ): δ H = 3.94 (s, 3H, 9-H), 3.96 (s, 3H, 10-H), 4.52 (s, 2H, 1-H), 6.90 (d, J = 8.4 Hz, 1H, 5-H), 7.47 (dd, J = 8.5, 2.0 Hz, 1H, 4-H), 7.52 (d, J = 2.1 Hz, 1H, 8-H); 13 C NMR (150 MHz, CDCl 3 ): δ LRMS m/z (CI + ): 222 [M+H] + , 165 [M-CH 2 N 3 ] + ; HRMS m/z (CI + ): Found 222.0878 [M+H] + ; C 10 H 12 N 3 O 3 requires 222.0879. 2-azido-1-(3,5-dimethylphenyl)ethanone, 16d 2-Bromo-1-(3,5-dimethylphenyl)ethanone 4 (3.44 g, 15.1 mmol) was dissolved in anhydrous DMSO (15 mL) and the mixture was cooled on ice. Sodium azide (1.18 g, 18.2 mmol) was added in one portion and the reaction was stirred under argon at RT for 16 h. An extra portion of sodium azide (200 mg) was added and the reaction was left to stir for a further 1 h. A colour change from yellow to deep orange was observed. The

Synthesis, Characterization and Antimicrobial Activity of 3-Acetyl-4-hydroxy-6-methyl-(2H)pyran-2-one Schiff Base with 2,2'-(Ethylenedioxy)diethylamine and its Co(II), Ni(II) and Cu(II) Complexes

Asian Journal of Chemistry

The commercially available aromatic polyketones 1a-d were utilized for the synthesis of the multi-arm1,2,3-selenadiazole derivatives 3a-d. The preparation starts with the reaction between compounds 1a-d and p-toluenesulfonyl hydrazide to give the corresponding tosylhydrazones 2a-d. Subsequent reaction with selenium dioxide leads to regiospecific ring closure of the tosylhydrazones to give the target multi-arm 1,2,3selenadiazole derivatives in high yield. A 1,2,3-selenadiazole derivative 3e containing an epoxide ring was also prepared. The structures of all the synthesized compounds were confirmed on the basis of spectral and analytical data. The compounds were screened in vitro for their antimicrobial activity against various pathogenic bacterial and Candida strains obtained from King Abdullah Hospital in Irbid-Jordan. Compounds 3a, 3c and 3e were found to be highly active against all the selected pathogens. Compound 3e showed an inhibition zone of 13 mm against the highly resistant P. aruginosa.

Synthesis and Antimicrobial Evaluation of Some New Pyrazoline Derivatives

Indian Journal of Applied Research, 2011

A series of 5-o xohexannitrile derivatives IIa-d was prepared by react ion of acry lonitrile with ketones Ia-d. On the other hand, semicarbazone derivatives IVa-d were obtained upon reaction of IIa-d with semicarbazide. Hydrolysis and esterification in one step reaction of δ-ketonitrile IIa-d resulted in the formation of the corresponding δ-ketoesters Va-d. The δ-ketoesters Va-d is readily cyclized to the corresponding cyclohexan-1,3-diones VIa-d when heated with alcoholic sodium metho xide. Moreover, coupling o f VIa, VIb and VId with aryl diazoniu m chlo ride afforded the corresponding 2-(ary l diazenyl) derivatives VIIa-f, respectively. Furthermo re, bis-(2,6-diketo-3-phenylcyclohexyl)methane VIII was synthesized by condensing VIa with benzaldehyde. Bro mination of VId in d ilute acetic acid afforded the corresponding bromo derivative IX. Heating of cyclohexanone-2-methyl propionate in alcoholic sodium metho xide affo rded bicycle[1,3,3]nonan-2,9-dione X. These compounds were characterized by analytical and spectral analyses and screened for their antibacterial activity against Gram-possitive bacteria and Gram-negative bacteria. The synthesized compounds (VIIa-f)-X showed significant antibacterial activ ity against P. Aeruginosa (MIC 0.30-0.45 μg/ mL), S. Aureus (MIC 0.25-0.45 μg/ mL) and B. Subtilis (MIC 0.20-0.45 μg/ mL) and exh ibited moderate antibacterial activ ity against E. Coli (M IC 0.30-0.45 μg/ mL) co mpared with the standard drug Ciproflo xacin.

Synthesis of Some New 4-(BENZOTHIAZOLYLAMINO)-PYRAN-2-ONE Derivatives and Their Antibacterial Activity

European Chemical Bulletin, 2017

Novel 4-substituted pyran-2-one derivatives were synthesized by condensation of 6-methylpyran-2-ones and corresponding 2aminobenzothiazoles. Condensation of 4-chloro-6-methyl-2H-pyran-2-one 2a and 2-aminobenzothiazoles 3(a-c) afforded corresponding 4-(2-benzothiazolylamino)-6-methyl-2H-pyran-2-one 4a, 4-(4-methyl-2-benzothiazolylamino)-6-methyl-2H-pyran-2-one 4b and 4-(5,6dimethyl-2-benzothiazolylamino)-6-methyl-2H-pyran-2-one 4c. By condensation of 4-chloro-3-nitro-6-methyl-2H-pyran-2-one 2b and 2aminobenzothiazoles 3(a-d), 4-(2-benzothiazolylamino)-3-nitro-6-methyl-2H[1]-pyran-2-one 4d and 4-(6-ethoxy-2-benzothiazolylamino)-3-nitro-6-methyl-2H[1]-pyran-2-one 4e were synthesized. The synthesized products were characterized on the basis of IR, 1 H-NMR and 13 C-NMR spectra. Compounds 4a-4e were screened for their antibacterial activity against S. Aureus, E. Coli and Klebsiella. Their antibacterial activity is examined by measuring the zones of inhibition around the disks impregnated with the corresponding product solutions in N,N-DMF concentration 2 mg mL-1 , 4 mg mL-1 and 6 mg mL-1 and results are reported.

Synthesis of some new 1-(5-((1H-pyrazol-1-yl)methyl)-2-aryl-1,3,4-oxadiazol-3(2H)-yl) ethanone derivatives and study their antimicrobial activity

2021

Ethyl 2-(1H-pyrazol-1-yl)acetate (1) was synthesized by the reaction of ethylchloroacetate with 1H-pyrazole, Then compound (1) refluxed with hydrazine hydrate to get 2-(1H-pyrazol-1-yl) acetohydrazide (2). Compound (2) was reaction with appropriate aryl aldehyde to get schiff bases N'-arylidine-2-(1H-pyrazol-1-yl)acetohydrazide derivatives (3a-3f). schiff’s base (3a-3e) were cyclized by reflux with acetic anhydride to get new 1-(5-((1H-pyrazol-1-yl)methyl)-2-aryl-1,3,4-oxadiazol-3(2H)-yl)ethanone derivatives (4a-4e). The structures of the synthesized compounds were characterized by IR, 1H-NMR, 13C-NMR, mass spectra, and elemental analysis data. Synthesized compounds (4a-4e) were evaluated as antibacterial agents against some common pathogenic bacteria Gram-positive (Staphylococcus aureus, Streptococcus pyogenes) and Gram-negative bacteria (Escherichia coli, Psuedomonas aeruginosa). The result of antibacterial activity was compared with standard drugs (Ciprofloxacin and Tetracycl...

Synthesis and Antimicrobial Activity of Pyrazolo[4,5-e] Pyrimido[2,1-b]Pyrazines

2020

Based on the potent biological activity of pyrazolo derivatives, we carried out synthesis of 3-amino-4-imino-2-N(substituted)pyrazolo[4,5-e]pyrimido[2,1-b] pyrazines (3a-j) have been reported from condensation of 3-cyano-4-imino-2(methylthio)-4H-pyrimido[1,2-a]pyrazine (1) and substituted hydrazines and hydrazine benzothiazole (2a-j) using dimethyl formamide as reaction solvent and anhydrous K2CO3 as reaction catalyst. These synthesized compounds were further screened for antibacterial activity and cytotoxicity study.

STUDIES ON SOME NEW PYRAZOLO[3,4-c]PYRIDINE DERIVATIVES AS ANTIMICROBIAL AGENTS

2010

The increasing clinical importance of drug-resistant bacterial and fungal pathogens has lent additional urgency to microbiological research and novel antimicrobial compounds development. For this aim, a series of N-[(Benzhydryl) / (l-phenylethyl)]-2-pyrazolo[3,4-c]pyridin-l-yl acetamide derivatives (3a-m) were synthesized by reacting 2-chloro-N-(benzhydryl)acetamide (la) / 2-chloro-N(1-phenylethyl)acetamide (lb) and pyrazolo[3,4-c]pyridine derivatives (2). The chemical structures of the compounds were elucidated by elemental analyses, IR, H-NMR, FAB-MS spectral data. Their antimicrobial activities against E. coli (ATCC 11229), S. aureus (ATCC 6538), B. cereus (ATCC 11778), P. mirabilis (ATCC 14153), P. aeruginosa (ATCC 1539), K. pneumoniae (ATCC 4352), C albicans (ATCC 26555), C guilliermondii (KUEN 998), C pseudotropicalis (kefyr) (KUEN 1014), and C krusei (ATCC 6258) were investigated. The results showed that some of the compounds have slight activity against B. cereus and S. aure...