Synthesis of Novel Alkyl (dialkoxyphosphoryl)-1H-indole-3-yl)acetate, Dialkoxyphosphoryl[2,3-b]indole-3-carboxylate and Dialkyl methylphosphonate Derivatives Using Wittig-Horner Reagents and their Antimicrobial Activity (original) (raw)
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Synthesis, Antimicrobial, and Antioxidant Activity of New α-Aminophosphonates
Phosphorus, Sulfur, and Silicon and the Related Elements, 2011
A number of benzimidazole compounds namely, N-(4-(1H-benzimidazol-2-yl)phenyl)-4-(1H-benzimidazol-2yl)-benzamide derivatives (8-10) and N-(3-or 4-(1H-benzimidazol-2-yl)phenyl)-2-phenyl-1H-benzimidazole-5carboxamide derivatives (18-21) were synthesized and antibacterial and antioxidant activities were evaluated. Antibacterial activities of 9, 10, 18, and 20 against MRSA-isolate are equal to ampicillin. Compounds 18, 19, and 21 displayed better antifungal activities against Candida albicans. Antioxidant properties were evaluated by several methods, such as inhibition of lipid peroxidation, superoxide anion production, and DPPH stable free radical, and also their effects on hepatic cytochrome P450 (CYP) dependent ethoxyresorufin O-deethylase (EROD) enzyme were determined in rats in vitro. Compounds 18 and 20 had strong scavenger effect on superoxide anion (90%, and 99%, respectively) at 10 -3 M concentration. Compound 19 showed significant inhibition on EROD activity with 98%, which is better than that of caffeine being a specific inhibitor of EROD activity (85%).
The Synthesis and Evaluation of Diethyl Benzylphosphonates as Potential Antimicrobial Agents
Molecules
The impact of substituent at phenyl ring of diethyl benzylphosphonate derivatives on cytotoxic activity was studied. The organophosphonates were obtained based on developed palladium-catalyzed α, β-homodiarylation of vinyl esters protocol. The new synthetic pathway toward 1,2-bis(4-((diethoxyphosphoryl)methyl)phenyl)ethyl acetate was proposed which significantly improves the overall yield of the final product (from 1% to 38%). Several newly synthesized organophosphonates were tested as new potential antimicrobial drugs on model Escherichia coli bacterial strains (K12 and R2-R3). All tested compounds show the highest selectivity and activity against K12 and R2 strains. Preliminary cellular studies using MIC and MBC tests and digestion of Fpg after modification of bacterial DNA suggest that selected benzylphosphonate derivatives may have greater potential as antibacterial agents than typically used antibiotics such as ciprofloxacin, bleomycin and cloxacillin. These compounds are highl...
Phosphorus, Sulfur, and Silicon and the Related Elements, 2013
Series of diphenyl 1-(arylamino)(pyridin-3-yl)methylphosphonates were obtained in high yields from the reactions of nicotinaldehyde with aromatic amines and triphenylphosphite in the presence of titanium tetrachloride as a catalyst. The structures of the synthesized compounds were confirmed by IR, 1 H NMR and mass spectral data and their purities were confirmed by elemental analyses. The synthesized α-aminophosphonates showed moderate to high antimicrobial activities against Escherichia coli (NCIM2065) as a Gramnegative bacterium, Bacillus subtilis (PC1219) and Staphylococcus aureus (ATCC25292) as Gram-positive bacteria and Candida albicans and Saccharomyces cerevisiae as fungi, at various concentrations (10-100 μg/mL). The lethal dose of the synthesized compounds was also determined and indicated that most compounds are safe to use.
Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates
International Journal of Medicinal Chemistry, 2011
α-Aminophosphonates are bioisosteres of amino acids and have several pharmacological activities. These compounds have been synthesized by various routes from reaction between amine, aldehyde, and phosphite compounds. In order to synthesize α-aminophosphonates, catalytic effect of CuCl2 was compared with FeCl3. Also all designed structures as well as griseofulvin were docked into the active site of microtubule (1JFF), using Autodock program. The results showed that the reactions were carried out in the presence of CuCl2 in lower yields, and also the time of reaction was longer in comparison with FeCl3. The chemical structures of the new compounds were confirmed by spectral analyses. The compounds were investigated for antifungal activity against several fungi in comparison with griseofulvin. An indole-derived bis(α-aminophosphonates) with the best negative ΔG in docking study showed maximum antifungal activity against Microsporum canis, and other investigated compounds did not have a...
Journal of Molecular Structure
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Two new categories of a-aminophosphonates molecules were synthesized and characterized by UV-Vis, IR, and NMR. Their spectral properties show a perfect convergence. Their biological activities were evaluated. Molecules 1a, 2a, and 1d present a greater antioxidant potential than BHT and vitamin C. The best anti-inflammatory activity is shown by the 2b molecule and that of 1a, 2a, and 2c molecules are closely comparable to that of diclofenac. The antibacterial activity of the synthesized compounds is significantly higher than the antibiotic amoxicillin. The hemolysis rate HR of compounds 1b, 1c, 2b, and 2c was lower than 5%.
SYNTHESIS, CHARACTERIZATION AND BIO-ACTIVITY OF SOME NEW
ABSTRACT. A convenient and efficient one-pot reaction has been employed for the synthesis of new α- aminophosphonates 4a-4k via Kabachnik-Fields reaction in 65-82 % yields. In the procedure developed, equimolar quantities of 2-amino-4-methylphenol 1, various aromatic aldehydes 2a-2k and dimethylphosphite 3 in dry toluene were reacted under reflux for 4-6 h. The products were characterized by IR, 1H, 13C and 31P NMR spectra and elemental analysis. All the synthesized compounds were screened for in vitro antibacterial activity (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae, Salmonella typhimurium) and antifungal activity (Candida albicans, Aspergillus niger). 4a showed potent activity with lowest MIC value.
ChemInform, 1999
Fifteen heterocyclic phospho nate derivatives and their starting compounds have been evaluated in vitro for antibacterial and antifungal activities against standard strains: Enterococcus faecalis (A TCC 29212), Staphy lococcus aureus (ATCC 2921)), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 2785 3) and yeast-like fungi ; Candida albicans and Candida tropicalis. The compounds newly synthesised have been identified by IH-NMR,. FT-IR and micro analysis. Among the tested compounds 12, 13, 16, 17, 18, 22 and 23 are found effective to inhibit the growth of Candida albicans and Candida tropicalis at the MICs between 100-800 Ilg/mL. The compounds tested here generally do not exhibit considerable antibacterial activity at the concentratiolJ studied (100-800 Ilg/mL), except compound 18 which exhibits antibacterial activity against gram-positive bacteria at the MIC of 400 Ilg/mL.