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Abstract

The synthesis of many new 2-substituted 1,3,4-oxadiazoles from creatinine is studied in this research. The ester of creatinine 1a was formed by the reaction of creatinine with ethylchloroacetate, and then with two of alkyl halides to produce compounds 2a-2b. Following that, hydrazide derivatives 3a-3b were produced by compounds 2a-2b with semicarbazide hydrochloride. These hydrazides were cyclized with 5 percent sodium hydroxide to produce 1,3,4oxadiazole derivatives 4a-4b. The reaction of these compounds with aromatic aldehydes produced Schiff bases 5a-5d. Finally, diazetidine 6a-6h and βlactam 7a-7d derivatives on position (2) from 1,3,4-oxadiazole were formed by reacting Schiff bases with various reagents. FT-IR spectroscopy and 1 H-NMR for some synthesized compounds were used to identify the newly synthesized compounds. In vitro, antioxidant activities of some synthesized compounds were also investigated with promising results.

Modification, Characterization of New Thiazolidinone and Oxazolidinone Derived from Levofloxacin and Evaluation of Anti-Oxidant

“…The 1 H-NMR spectrum data for compound [10] as shown in fig- 8, appeared doublet signal at δ= 1.44 ppm (3H, CH3-CH, CH3 in oxazine ring); singlet signal at δ= 2.27 ppm (3H, -CH3-N-); triplet signal at δ= 3.37-3.44 ppm (2H, -N-CH2-CH2-N-, 2CH2 in piperazine ring); singlet signal at δ= 4.13 ppm (2H, thiazolidin-4-one ring); while appeared multiplet signal at δ= 7.45-7.96 ppm (5H, Ar-H); singlet signal at δ= 8.80 ppm (1H,-N-CH=C(CO)2); 8.99 ppm (s, 1H, -CO-NH). Schiff bases [3][4][5] were reacted with Chloroacetic acid to synthesize the oxazolidin-5-one derivatives [6][7][8]. These compounds' FTIR spectra showed the disappearance of azomethine group absorption bands at (1639-1641) cm -1 , with bands of (C=O oxazolidinone ring) at range (1230-1280) cm -1 , absorption bands for (C-H Arom.)…”

“…The 1 H-NMR spectral data for compound [6] as shown in Figure 9 In vitro antioxidant activity (DPPH. 2,2-diphenyl-1-picrylhydrazyl) [14,16] The activity of all the compounds [3][4][5][6][7][8][9][10] and the beginning drug levofloxacin was comparable to or slightly higher than the standard (ascorbic acid). The DPPH (2,2-diphenyl-1-picrylhydrazyl) assay method predestines it at different concentrations (25, 50 and 100) g/mL.…”

“…Among all chemicals,compounds [3,4,5,6,9,10] showed the most outstanding performance. When compared to some compounds that include amino groups, some compounds [4,7,10] bearing a Chloro group (electron-withdrawing group) at the para position demonstrated high antioxidant activity (electron donating group). Intense antioxidant action is shown by compounds [5,8,10] modified with halogen groups -Cl (electron-withdrawing group).…”

“…Heterocyclic compounds are among the most influential families of organic chemicals used in various biological disciplines because of their activity in multiple diseases. It has been used to create anticancer pharmaceuticals [5], anti-fungal [6], antioxidants [7] and anti-microbial [8]. Hugo Schiff was the first to report Schiff's bases in 1864.…”