Synthesis and biological activities of some 3- chloro-4-(substituted phenyl)-1-{(2-oxo-2-(5- phenyl-1H-tetrazol-1-yl) ethyl) amino} azetidin- 2-one as potential antibacterial agents (original) (raw)
Related papers
Synthesis and Biological Evaluation of Some Substituted Azetidinones
Condensation of acetophenone with thiourea in presence of halogen (Iodine) gives 2-amino-4-phenylthiazole (I). 2-Amino-4-phenyl-5-phenylazothizole (II) was prepared by coupling of phenyldiazonium chloride with 2-amino-4-phenylthiazole (I). A series of amide can be synthesized by treatment of appropriate substituted acid chlorides (III) with compound (II) using pyridine as solvent. All the synthesized compounds are characterized by the combination of elemental analysis and standard spectroscopic method. They are screened for anti-bacterial activity against Escherichia coli and Staphylococcus aureus as well as screened for antifungal activity against Aspergillus niger and Apergillus oryzae by cup plate method at 1μg/mL concentration in DMF. All the synthesized compounds showed moderate to good microbial activity.
Study on Synthesis of Some Novel Azetidinone Derivatives
International Journal of Pharmaceutical Sciences and Research
A series of five novel azetidinones were synthesized by cyclocondensation of various Schiff bases of naphthylamine with Chloroacetylchloride in the presence of triethylamine. Schiff's bases preparing from naphthylamine moiety by reacting the hydrazide of the parent compound with different aromatic or heterocyclic aldehydes under acidic conditions in ethanol and cyclocondensation of Schiff's bases with chloracetyl chloride in the presence of triethylamine and dioxane resulted in the formation of corresponding azetidinone derivatives. The newly synthesized compounds were characterized by IR, and mass spectra. The synthesized compounds were evaluated for antibacterial and antifungal activities by Agar diffusion method. All the compounds at a concentration of 1000,500,250,125 and 62.5μg/ml and compounds were screened for their antibacterial activity against Staphylococcus,aureus, Bacillus subtilis (Gram positive bacteria) Escherichia coli, Pseudomonas aeruginosa (Gram-negative bacteria) by disk diffusion method. Compounds showed good anti-bacterial activity against Staphylococcus aureus and Bacillus subtilis. Compounds SAz1 -5 exhibited good antifungal activity against Candida albicans fungus.
2019
A new series of 4-aryl-3-chloro-1-(3,5-dimethyl-isoxazol-4-yl)-azetidin-2-ones 4 have been prepared from 4-amino3,5-dimethylisoxazole 1. Compound 1 on treatment with aromatic aldehydes 2a-i furnishes the Schiff bases 3a-i, which are then reacted with chloroacetyl chloride in presence of triethyl amine to afford the title compounds viz., isoxazolyl azetidin-2ones 4a-i. The structures of β-lactams 4a-i have been confirmed by IR, 1H and 13C NMR and mass spectral data. QSRT studies have been performed, and the compounds 4a-ihave been evaluated for their in vitro antibacterial activity. Compounds 4b, 4c and 4d exhibited promising antibacterial activity.
In the present study new azetidinone derivatives containing sulfa drug moiety have been prepared by cyclocondensation of the Schiff bases derived from sulfa drugs with chloroacetyl chloride in the presence of triethylamine. The Schiff bases are prepared by the condensation reaction of the sulfa drug (sulfadiazine and sulfanilamide) with the 5-nitro-2-furancaroboxyaldehyde. The structure of the azetidinons were confirmed by elemental analysis (C. H. N.) and FT-IR, 1 H-NMR spectroscopy. The compounds were screened for their antimicrobial activity against Staphylococcus aureus, Escherichia coli, Aspergilus niger and Aspergilus flavus. The compounds exhibited good antimicrobial activity in comparison with standard drugs.
Synthesis, in Vitro Antimicrobial Activity of Schiff’s Base, Azetidinones and Thiazolidinones
International Journal of Current Pharmaceutical Research
Objective: The objective of the present study is to synthesize 3-Chloro-4-[3-(2,4-dichloro-5-fluoro phenyl)-1H-pyrazol-4-yl]-1-(substituted) azetidin-2-one [4a-n] and 2-[3-(2,4-Dichloro-5-fluoro phenyl)-1H-pyraol-4-yl]-3-(substituted phenyl)-1,3-thiazolidin-4-one [5a-n]. The structure of all synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral studies. Methods: The titled compounds 3-Chloro-4-[3-(2,4-dichloro-5-fluoro phenyl)-1H-pyrazol-4-yl]-1-(substituted) azetidin-2-one [4a-n] and 2-[3-(2,4-Dichloro-5-fluoro phenyl)-1H-pyraol-4-yl]-3-(substituted phenyl)-1,3-thiazolidin-4-one [5a-n] were synthesized by the reaction of N-{[3-(2,4-dichloro-5-fluoro phenyl)-1H-pyraol-4-yl] methylene } substituted anilin [3a-n] with chloro acetyl chloride and thioglycolic acid respectively. Compounds N-{[3-(2,4-dichloro-5-fluoro phenyl)-1H-pyraol-4-yl] methylene} substituted aniline [3a-n] were synthesized by the reaction of 3-(2,4-dichloro-5-fluoro phenyl)-1H-pyrazol-4-c...
2015
A novel series of azetidinone AZ1-6 been prepared from the building blocks 2, 3, 4 (trisubstituted benzaldehyde)-N-(6,7 substituted-1,3-benzothiazol-2-yl) semicarbazone [2.026a-o]. All of the synthesized compounds have been confirmed by elemental analyses, IR and H NMR spectral data. These newly synthesized compounds were screened for their antibacterial activity. Variable and modest activity was observed against the investigated strains of bacteria, however compounds AZ2, AZ3, AZ5 and AZ6 revealed significant antibacterial activity against Bacillus subtilis and Pseudomonas compared to the reference drug Procaine penicillin and Streptomycin.
Synthesis and Antifungal Activity of Some Azetidinones
SYNTHESIS, 2009
Ethyl-1H-benzotriazol-1-acetate 2 was prepared by reacting 1H-benzotriazole 1 in alcohol with ethyl bromoacetate in presence of anhydrous potassium carbonate, which was treated with hydrazine hydrate under reflux for 18-24 hours to obtain the intermediate 1H-benzotriazole-1-acetic acid hydrazide 3. This compound on Schiff's reaction with aromatic aldehydes in presence of solvent mixture yielded 2-(1H-benzotriazol-1-yl)-N'-(substituted phenyl/heteroaryl methylidene) acetohydrazide 4a-4j. This on reaction with monochloroacetyl chloride and triethylamine in dioxane at low temperature followed by heating at more than 100 0 C temperature gave N-substituted-2-azetidinones 5a-5j and were characterized. .The synthesized compounds exhibited moderate to good antifungal activity when tested in vitro against C.albicans. Compounds 5g and 5h were found to be the most active among all the compounds. To understand their interaction with receptor, these were docked into active site of CYT P-450(PDB-code:1EA1).
Antimicrobial studies of synthesized azetidinone derivatives from sulfamethoxazole moiety
2011
A series of novel Azetidinone derivatives have been synthesized from the intermediate schiff bases. Schiff bases are prepared from sulfamethoxazole moiety by reacting the hydrazide of the parent compound with different aromatic aldehydes. Cyclocondensation of schiff's bases with acetylchloride resulted in the formation of azetidinone derivatives. The products, characterized on the basis of satisfactory spectral data (IR, NMR, Mass spectroscopy), have shown moderate to good antimicrobial activity against some bacteria and fungi.
Synthesis and biological evaluation of azitidinone and their derivative as antimicrobial agents
In our present study Hydrazin hydrate is condensed with different substituted aromatic aldehydes to form respective schiff bases. The schiff bases are cyclised with chloroacetylchloride in triethylamine to yield the corresponding 2azetidinones.Structures of synthesized compounds are confirmed by physical & spectral analysis. The compounds are evaluated for their antimicrobial properties. All the compounds have shown comparable antimicrobial activities.The activities are due to C=O, C-N linkages in 2-azetidinones.