Synthesis and biological screening of a novel series of 3, 4, 5-trisubstituted phenoxyacetic acid analogs (original) (raw)
Related papers
2012
In present study, a novel series of trisubstituted phenoxyacetyl amino acids and peptide derivatives was synthesized by coupling 2-(2,6-dibromo-4-formylphenoxy)acetic acid with amino acid methyl ester hydrochlorides/peptide methyl esters using DIPC as coupling agent and TEA as base. The structures were elucidated by IR, 1 H NMR, 13 C NMR and MS spectral data as well as elemental analysis. The newly synthesized peptide derivatives were evaluated for antibacterial and antifungal potential against pathogenic microorganisms. Compounds Ig, k and In displayed potent antibacterial activity against gram-negative bacteria Pseudomonas aeruginosa, Escherichia coli and compounds Ic, Ih, l and Ij, m were found to be exhibit potent antifungal activity against pathogenic Candida albicans and dermatophytes, as compared to standard drugs ciprofloxacin and griseofulvin.
Synthesis, characterization and biological screening of some new aryloxyacetic acid analogs
Zenodo (CERN European Organization for Nuclear Research), 2008
A novel series of 2-(4-bromo-2-formyl-phenoxy)acetyl amino acid and peptide analogs was synthesized by the coupling of 2-(4-bromo-2-formyl•phenoxy)acetic acid with different amino acid methyl ester hydrochlorides, dipeptide and tripeptide methyl esters using dicyclohexylcarbodiimide as the coupling agent and N-methylmorpholine as the base. Structures of all the newly synthesized compounds were elucidated on basis of IR, NMR and MS spectral data as well as elemental analysis. On pharmacological screening, some peptide derivatives were found to exhibit potent bioactivity against gram-negative bacterium Pseudomonas aeruginosa, pathogenic fungus Candida albicans and earthworms Megascoplex konkanensis, Pontoscotex corethruses and Eudrilus sp. Dermatophytes were found to be moderately sensitive towards the newly synthesized analogs. Hydrolyzed peptide derivatives displayed better antimicrobial activity in comparison to corresponding esters.
Synthesis and Biological Screening of Novel Aryloxyacetic Acid Analogs
2009
A series of 5-Bromo- 2-formyl phenoxyacetyl amino acids and peptides have been synthesized by coupling of the 5-Bromo- 2-formyl phenoxyacetic acid with amino acid/methyl esters/dipeptides/ tripeptides using DCC as coupling agent and NMM as base. The structures were elucidated FTIR and 1 HNMR .The newly synthesized compounds were evaluated for their antibacterial, antifungal and anthelminitic activities. The compounds (2, 6, 11 and 13) were found to exihibit potent antibacterial activity against Bacillus subtilis, Staphylococcus aureus (gram positive bacteria) and Escherichia coli (gram negative) bacterias.The compounds (5, 6 and 13) were found to exihibit potent antifungal activity against Candida albicans and Aspergillus niger. The moderate to good anthelminitic activity was shown by the synthesized compounds (7 and 13) against Eudrilus spieces.
2012
A series of 4 - [(4)5 - imidazolyl] benzoic acids derivatives of amino acids and peptides were synthe sized by reacting 4 - [(4)5 - imidazoyl benzoic acid with amino acids and dipeptides. The structures of the synthesized compounds were characterized by FTIR, 1 13 C NMR, and GC - MS data and the synthesized compounds were screened for their anthelmintic act ivity and the results showed that the compounds containing Ala - Ile and Pro - Val exhibited potent anthelmintic activity against Eudrillus Eugenia at that of standard Mebendazole a concentration of 100mg/50ml. The synthesized compounds were also studied for t heir insecticidal activity and they showed moderate to less insecticidal activity as compared to the standard drug Chloropyri fos.
Anais Da Academia Brasileira De Ciencias, 2018
Thirteen natural products derivatives of hydroxyl amide class, three described for the first time, were synthesized by reaction of three indole acids and 3,4,5-trimethoxybenzoic acid with six different amino alcohols in the presence of triphenylphosphine and N-bromosuccinimide. The derivatives were tested against the Gram (+) bacteria Staphylococcus aureus and Bacillus cereus, Gram (-) Pseudomonas aeruginosa and Escherichia coli, besides the yeast Candida albicans. One of the compounds (7) was selectively active against C. albicans (91.3 ± 0.49% inhibition) showing a great potential as a new drug lead, since it was more active than the positive control, miconazole (88.7 ± 2.41% inhibition). Regarding bacterial inhibition, compounds demonstrated mild activity, but inhibition of compounds 9, 10 and 13 towards E. coli is of interest since it is difficult to find drugs selectively active against Gram (-) bacteria. Most of the compounds were very active in the acetylcholinesterase inhibition assay. Compound 7 was again the most active (93.2 ± 4.47%), being more potent than the control galantamine (90.3 ± 0.45%). The most active gallic acid derivatives, compounds 3, 7 and 8 have in common, besides gallic acid skeleton, a (CH 2) 2 OH group, which may be one of the structural requirements for AChE inhibition.
Asian Journal of Pharmaceutical and Clinical Research
Objective: A novel series of substituted 3,3-diphenyl propanamide derivatives (I-VIII) were synthesized by reacting 3,3-diphenyl propanoyl chloride with different amines/amino acids, and all the derivatives were investigated for anthelmintic, antibacterial, and antifungal activity.Methods: All the compounds were characterized by infrared (IR) and1H- nuclear magnetic resonance spectrometry data. The synthesized derivatives were investigated for their anthelmintic activity employing housefly worms method and earthworm species model. The antibacterial and antifungal activity was performed employing cup plate method.Results: The synthesized compounds (VII and VIII) exhibited maximum anthelmintic activity as compared with standard drug albendazole at doses of 50 and 100 mg/mL, due to minimal paralyzing and death time in both housefly and earthworm models. The compounds (IV, VII, and VIII) at 50 μg/mL exhibited maximum activity against Gram-negative bacterial strains, namely, Escherichia ...
Synthesis, Characterization and Antibacterial Activity of Some Amino Acid Derivatives
2017
The present work includes the synthesis of glycine and L-amino acid derivatives 6-10 (A,B) via Schiff`s bases 3 (A,B), which were obtained from the reaction of 2-aminopyridine 2 with benzaldehyde 1A or 4-chlorobenzaldehyde 1B. The reaction of 3 (A,B) with benzoyl chloride yielded benzamide derivatives 5 (A,B). The synthesis of 6-10 (A,B) has been performed by the reaction of 5 (A,B) with (glycine, L-alanine, L-phenylalanine, L-aspartic acid and L-asparagine). Infrared and nuclear magnetic spectroscopic techniques Fourier Transform Infrared (FT-IR), Proton Nuclear Magnetic Resonance (1H-NMR) and Carbon-13 nuclear magnetic resonance (13C-NMR) were used to characterize the newly synthesized compounds. The antibacterial activity of final products has been evaluated against two kinds of Gram-positive and Gram-negative bacteria (Staphylococcus aureus and Klebsiella pneumonia). Overall, results indicate a lower and moderate antibacterial activity in comparison with meropenem as a reference...
REPORT - Synthesis of promising antibacterial and antifungal agents: 2-[(4-Chlorophenyl)sulfonylamino]-N-(un/substituted-phenyl)acetamides
2020
In the presented work, 2,3-dihydro-1,4-benzodioxin-6-amine (1) was reacted with 4-chlorobenzenesulfonyl chloride (2) in presence of aqueous basic aqueous medium to obtain 4-chloro-N-(2,3-dihydro-1,4-benzodioxin-6-yl)benzenesulfonamide (3). In parallel, various un/substituted anilines (4a-l) were treated with bromoacetyl bromide (5) in basified aqueous medium to obtain corresponding 2-bromo-N-(un/substituted)phenylacetamides (6a-l) as electrophiles. Then the compound 3 was finally reacted with these electrophiles, 6a-l, in dimethylformamide (DMF) as solvent and lithium hydride as base and activator to synthesize a variety of 2-[[(4-chlorophenyl)sulfonyl](2,3-dihydro-1,4-benzodioxin-6-yl)amino]-N-(un/substituted)phenylacetamides (7a-l). The synthesized compounds were corroborated by IR, 1H-NMR and EI-MS spectral data for structural confirmations. These molecules were then evaluated for their antimicrobial and antifungal activities along with their %age hemolytic activity. Some compoun...
Pharmaceutical Chemistry Journal, 2014
Interaction of 2-chloro-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)acetamide with a-, band w-amino acids was used to synthesize new amino-acid derivatives of 9,10-anthraquinone. Experimental testing of the antimicrobial actions of the compounds synthesized demonstrated antibacterial activity against Mycobacterium luteum and antifungal activity against Aspergillus niger and Candida tenuis. These results from experimental testing of biological activity are consistent with results obtained by predictions using the computer program PASS. The prediction identified the need for further study of the antitumor and antioxidant actions of the newly synthesized amino acid derivatives.