INTRODUCTION:

As logical as the chemistry of aromatic or aliphatic molecules is that of heterocyclic ones. Because of its theoretical and practical implications, their study is highly interesting. Oxazolidinone derivatives are a class of synthetic antibiotics that inhibit bacterial growth by blocking protein synthesis. Oxazolidinones are chemically defined by a five-membered heterocyclic ring structure with one oxygen atom, one nitrogen atom, and three carbon atom^1,2. The carbon between the nitrogen and oxygen is oxidized to ketone. Oxazolidinones can exist in different structural isomers, such as 2-, 3-, and 4- oxazolidinone, depending on the position of the oxygen and nitrogen atoms in the ring.

Oxazolidinones bind to the 50s subunit of the ribosome, inhibiting an early step in the initiation phase of protein synthesis. The physical properties of the oxazolidinones with the molecular formula C₂H₅NO₂, Molecular weight: 87.08g/ml, Molar mass: 73.0938 g/mol, Density: 1.063 g/ml, Boiling point: 200°C (392°F;473K) 20 torr, Melting point: 90°F (194°F;363k). Oxazolines are unsaturated analogs of oxazolidines. Several oxazolidine derivatives occur naturally, some occur as post-translation modification of problems^3-7.

In contemporary medicinal chemistry, creating novel drugs based on biologically active oxazolidine scaffolds is a sensible and promising approach. Solvent-free synthesis is used to boost efficiency and lessen the negative effects of pharmacological catalysts. According to the goal of green chemistry, the identification of prospective drug-like compounds was made possible by current synthetic studies of oxazolidine analogs and biological investigation of their anticancer, antibacterial, antimicrobial, anticonvulsant, and antioxidant properties^8-16. We aim to correlate the available statistics on multi-targeted inhibitors with the OZD nucleus in light of the nucleus's multi-targeted functioning. This could serve as a standard for changing existing ligands to create new ones with stronger binding associations. The need for sophisticated and effective methods to create the heterocyclic lead oxazolidine as a crucial class of compounds for novel drug development has arisen due to the predominance of aromatic substituted oxazolidine core in physiologically active compounds. To give researchers a broad picture of recent advancements in their field, this review aims to compile the statistical report of the previous five-year research on the synthesis and biological activity of heterocyclic systems with oxazolidine fragments in molecules.

Biological Activity of Oxazolidine Derivatives:

Anticancer Activity:

Eneama WA et al synthesized novel isoxazolidine compound 5-(3-Chloro-ph)-3-(4-Methoxy-ph)-2-Ph-tetra-hydro4H-Pyrolo-[3,4-D] Isoxazol-4,6(5H)-Dion (IZ3) for anticancer efficacy using MTT assays against MCF-7 and HdFn cell lines, alongside normal cells (Figure 1). Structural elucidation employed FT-IR, ¹³C-NMR, ¹H-NMR, and E-1 mass spectroscopy. The compound IZ3 with an IC50 value of 32.49 µg/ml, shows potent against antitumor activity in MCF-7 cells compared to HdFn. The increased activity of IZ3 due to linked to the para methyl group’s role as an electron-donating group in the phenyl moiety and (NO2) role as an electron-withdrawing group. Finally, we conclude that the above compound has better anticancer activity¹⁷.

Figure No. 1: Chemical structure of 5-(3-Chloro-ph)-3-(4-Methoxy-ph)-2-Ph-tetra-hydro4H-Pyrolo-[3,4-D] Isoxazol-4,6(5H)-Dion

Armentano B et al evaluated the in vitro antiproliferative activity of some 5-(carbomoylmethylene)- oxazolidine- 2-ones on MCF-7 AND HeLa cells measured by MTT assay. Among the 9 tested derivatives, 4 displayed a good anticancer potential (Figure 2). Particularly, (CE)-2-(3-benzyl-4, 4-dimethyl-2-oxooxazolidin-5-ylidine)-N, N-dimethylacetamide (OI) compound showed IC50 values of 17.66 and 31.10µM for MCF-7 and HeLa cancer cells. OI can induce apoptosis through the mitochondrial intrinsic pathway, increasing ROS production and affecting mitochondrial functions. Finally, we conclude that the above compound showed better activity against MCF-7 and HeLa cancer cells¹⁸.

Figure No. 2: Chemical structure of 5-(carbomoylmethylene)- oxazolidine- 2-ones

You X et al developed a novel and sustainable synthetic approach with oxidant free. Employed tert-butoxycarbonyl (BOC) protected p-quinoamines as substrate and BF₃.Et₂O is a catalyst to mediate intramolecular oxo-Michael additions reactions, thus efficiently synthesizing structurally diverse target molecules with yields ranging from 54% to 98%. Their anti-proliferative activity in A549, T24, MCF-7, and HeLa cell lines was assessed in vitro. The 10 compounds are synthesized by H-NMR, C-NMR, and HRMS. Among these, 3-benzyl-3a-ethynyl-3,3a,7,7a-tetrahydrobenzo[d]oxazole-2,6-dione(2x) displayed the most potent anti-proliferative effect with IC50 of 9.24, 4.10, 9.48 and 4.13µM without affecting normal cells (Figure 3). The IC50 value of cytotoxicity of 2x in L-02 cells was 25µM, which was several times higher than the detected cancer cells. Furthermore, the anti-tumor activity of these structurally unique oxazolidin-2-one derivatives is reported¹⁹.

Figure No. 3: Chemical structure of 3-benzyl-3a-ethynyl-3,3a,7,7a-tetrahydrobenzo[d]oxazole-2,6-dione(2x)

Antimicrobial Activity:

Qabel HA et al synthesized 1-phenyl-2-acetoamino-4[(4-substituded)-oxazolidin-4-one-3-yl)-3-pyrazolidinone-2-yl] (Figure 4). The 5 compounds were characterized by FTIR, H-NMR, and C-NMR spectroscopy. The synthesized compounds were subjected to testing against gram-negative bacteria namely, Escherichia coli as well as gram-positive bacteria namely Staphylococcus aureus. Compounds 13, 15, and 16 showed the highest antimicrobial activity against Escherichia coli and compound 14 showed moderate inhibition against Escherichia coli. The compound 17 namely 1-phenyl-2-acetoamino-[(phenyloxazolidin-4-one-3-yl)-3-pyrazolidione-2-yl] has a zone of inhibition =17 for S.aureus and zone of inhibition= 19 for E.coli was resulted as strong inhibition against antimicrobial activity. Finally, we concluded that the above compound has better activity against the micro-organism²⁰.

Figure No. 4: Chemical structure of 1-phenyl-2-acetoamino-4[(4-substituted)-oxazolidine-4-one-3-yl)-3-pyrazolidinone-2-yl]

Patekar M et al synthesized of novel (5S)-5-(Aminomethyl)-3-[4-(6,7-dihydrothieno[3,2-C]pyridin-5(4H)-yl)phenyl]-1,3-oxazolidin-2-one by agar diffusion method (Figure 5). The synthesized 14 compounds (11a-n) were characterized by IR, MS, H, and C-NMR. Synthesized compounds (11a-n) were tested for antibacterial activity against a panel of gram-positive comprising staphylococcus aureus (ATCC6051), streptococcus pyogenes (ATCC12344), Bacillus subtillis (ATCC6051), Bacillus pumilus (ATCC27142) and Enterococcus faecalis (NCIM5253). The derivative from the above compound 11a (zone of inhibition = 15±0.5 for ATCC5638, 13±0.4 for ATCC12344, 13±0.3 for ATCC6051, 13±0.7 for ATCC27142, 13±0.5 for NCIM5253), compound 11c (zone of inhibition= 18±0.2 for ATCC5638, 16±0.7 for ATCC12344, 15±0.5 for ATCC6051, 14±0.4 for ATCC27142, 13±0.5 for NCIM5253) and compound 11e (zone of inhibition= 16±0.4 for ATCC5638, 13±0.3 for ATCC12344, 14±0.2 for ATCC6054, 15±0.6 for ATCC27142, 12±06 for NCIM5253) showed higher activity against a panel of gram-positive bacteria. Finally, we concluded that the above compound showed better activity against microorganisms than Linezolid and Tedizolid²¹.

Figure No. 5: Chemical structure of (5S)-5-(Aminomethyl)-3-[4-(6,7-dihydrothieno[3,2-C]pyridin-5(4H)-yl)phenyl]-1,3-oxazolidine-2-one

Pendem O et al synthesized 5-(((2-chloroquinoxalin-3-yl)methyl)-3-(3,4-substituted phenyl)oxazolidin-2-one by the reaction of 2,3-dichloroquinoxaline(4) with 5-(aminomethyl)-3-(3,4-substitutedphenyl) oxazolidin-2-ones (Figure 6). The structure of the resulting 12 compounds was identified and confirmed by elemental analysis and IR, Mass, H-NMR, and C-NMR spectroscopies. The anti-bacterial activity was assayed by the agar plate disc diffusion method. All synthesized compounds were tested against micro-organisms such as staphylococcus aureus, Bacillus subtillis, Escherichia coli, and Pseudomonas aeruginous strains. The anti-fungal activity was assayed by the sabouraud dextrose agar media plate disc diffusion method. All the synthesized compounds were tested against micro-organisms such as Aspergillus niger and Candida albicans. Among these compounds, 6a,6e,6h, and 6I show high activity against anti-bacterial activity as compared to ampicillin. Among these, the 6k compound has highly active with a zone of inhibition of 17mm in Aspergillus niger and 15mm in candida albicans as compared to fluconazole²².

Figure No. 6: Chemical structure of 5-(((2-chloroquinoxalin-3-yl)methyl)-3-(3,4-substituted phenyl)oxazolidine-2-one

ANTIBACTERIAL ACTIVITY:

Jin B et al synthesized 3-(3-pyridyl)-oxazolidone-5-methyl ester derivatives. All compounds were characterized by H-NMR, C-NMR, and LC-MS. These synthesized compounds are tested against Staphylococcus aureus, streptococcus pneumoniae, Bacillus subtilis, and Staphylococcus epidermidis. Among them, the compound (R)-(3-(6-(4-(cyclohexyl carbamoyl) piperazine-1-yl) pyridine-3-yl)-2-oxooxazolidin-5-yl)methyl methanesulfonate has the most potent activity with a MIC of 16 µg/ml against B.subtilis (Figure 7). Additionally, the anthelmintic activity test demonstrated that the compound 11b had the most significant anthelmintic effect. Finally, we concluded that the above compound showed better activity against gram-positive bacteria²³.

Figure No. 7: Chemical structure of (R)-(3-(6-(4-(cyclohexyl carbamoyl)piperazine-1-yl)pyridine-3-yl)-2-oxo oxazolidine-5-yl)methyl methanesulfonate

A new series of (s)-1-{3-[4-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-yl methyl}-3- substituted derivatives have been synthesized by Patekar MR et al in 2021 (Figure 8). The 15 compounds are characterized by IR, NMR, and Mass spectroscopies, compounds are invitro evaluated for their efficacy as an antibacterial agent against gram-positive bacteria such as Bacillus subtillis, staphylococcus aureus, staphylococcus epidermidis, and streptococcus pyogens. Among these 5 compounds (19k,19l,19m,19n, and 19o) show moderate activity against gram-positive pathogenic strains. The IR Spectrum of analogs showed the absorption band in the region of 1710-1780cm⁻¹which is characteristic of the carbonyl group of urea. Smaller alkyl groups in 19k(methyl substitution) and 19l(dimethyl substitution) enhanced the antibacterial activity as compared to another alkyl group. The compounds 19k and 19l have the most potent activity with MIC values of 18.2±0.2mm and 16.4±0.6 against Bacillus subtillis²⁴.

Figure No. 8: Chemical structure of (s)-1-{3-[4-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-3-fluoro-phenyl]-2-oxo-oxazolidine-5-yl methyl}-3- substituted derivatives

The heterocyclic compound (1,3-oxazolidine- 5-one derivative) was prepared by the reaction of the primary aromatic amino compound, aromatic carbonyl compounds, and chloroacetic acid. The synthesized compounds are characterized by H-NMR and FT-IR analysis. The biological efficacy was evaluated according to maximum inhibitory concentration (MICs) toward Staphylococcus aureus and Escherichia Coli. The compound J4 has MIC was 210µg ml^-1 against two pathogenic bacteria. In particular, compound J4 recorded MIC reached 240µg ml^-1 against S.aureus growth. However, the compound J3 maximum inhibition zone (16mm) against S.aureus at a concentration of 600 µg ml^-1. The compound J4 (600µg ml^-1) exhibited a zone of inhibition that reached 13mm and 12mm against S.aureus and E.coli. Finally, the 3’ –(pyrinidin-2-yl) spiro[indoline-3,2’- oxazolidine]-2,5’-dione(J4) was best compound synthesized inhibited the growth of gram-negative and gram-positive bacteria²⁵(Figure 9).

Figure No. 9: Chemical structure of 3’ –(pyrinidin-2-yl) spiro [ indoline-3,2’- oxazolidine]-2,5’-dione(J4)

In 2021, Jiang J et al synthesized a series of novel oxazolidinone derivatives with nitrogen-containing fused heterocyclic moiety (Figure 10). The 8 compounds were characterized by H-NMR and MS spectra. The antibacterial activities were evaluated against Staphylococcus aureus and vancomycin-resistant Enterosphere. They exhibited potent in vitro antibacterial activity as compared with Linezolid and Radezolid. Among these compounds, compound 3b showed the most potent antibacterial activity with MIC values of 0.5-1 µg/ml against five gram-positive compared to Linezolid²⁶.

Figure No. 10: Chemical structure of oxazolidinone analogs containing a nitrogen-containing fused heterocycle

Antioxidant activity:

Damdoom WK et al synthesized a novel oxazolidine derivative in a step procedure. The first step included the synthesis of Schiff base A1-A5 in 72-88% yields by condensation and the second step included cyclization of A1-A5 with glycolic acid to obtain desired oxazolidine derivatives B1-B5 in 44-60% yields. The structure of the prepared 5 compounds was characterized using FT-IR, H-NMR, and C-NMR spectroscopy. The H-NMR analysis data of the products B1, B2, and B3 showed singlet singles attributed to the CH₂group of oxazolidine derivatives at (4.92-4.91, 4.13, 4.31-4.07). The C-NMR spectra showed signals at (66.9, 72.6, 61.4). Compared to other synthesized compounds, (N-(2-(4-hydroxy-3-methoxyphenyl)-4-oxazolidine-3-yl) isonicotinamide) had the highest antioxidant activities with IC50= 10 mg/ml (Figure 11). Finally, this study has concluded that the above compound showed better antioxidant activity²⁷.

Figure No. 11: Chemical structure of N-(2-(4-hydroxy-3-methoxyphenyl)-4-oxazolidine-3-yl) is nicotinamide

Anti Convulsant Activity:

In 2022, Al-Tannak NF et al identified a novel triazolyl-oxazolidinone derivative (PH-192), as a potential anti convulsant agent. PH-192 demonstrated protection comparable to phenytoin against both chemically and electrically induced seizures. But after 30 minutes, PH-192 showed no signs of protection. So looked into stability indicating test of PH-192 in plasma and other solutions. To examine the stability of PH-192 for 90 minutes in human plasma under acidic, basic and oxidative using UHPLC. PH-192, a thiophene glycinyl- oxazolidinone-containing derivative produced a dose-dependent production from seizures induced by using 6HZ stimulation with an estimated ED50 of 34.5mg /kg and 90mg/kg in mice and rats. The LOQ was found to be 1µg/ml for PH-192 with an RST% of 58%. LOD for PH-192 was found to be 0.33µg/ml using 10µL as an injection volume. Therefore, it is a potent candidate that can be subjected to pharmacological studies in vivo in animal anti-convulsant models²⁸.

Figure No. 12: Chemical structure of synthesized triazolyl-oxazolidinone derivative

CONCLUSION:

Analyzing literature reviews shows that oxazolidinone and its derivatives are a significant class of compounds in medicine with a variety of therapeutic potential, including anti-cancer, anti-microbial, anti-oxidant, anti-bacterial, and anti-convulsant properties. As a result, researchers are very interested in creating oxazolidinone derivatives. The primary focus of this study of the literature is on synthetic active molecules of oxazolidinone properties which are crucial to the medical field. Their highly active oxazolidinone derivatives may be used to discover new products with potential medical uses in the future.

ACKNOWLEDGEMENT:

The authors would like to express their gratitude to the management of Vivekanandha Pharmacy College for Women Sankari for providing all of the facilities in the pharmaceutical chemistry department.

CONFLICT OF INTEREST:

The authors does not disclose any conflict of interest.

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Received on 30.12.2024 Revised on 29.01.2025

Accepted on 17.02.2025 Published on 14.04.2025

Available online from April 18, 2025

Asian J. Research Chem.2025; 18(2):81-86.

DOI: 10.52711/0974-4150.2025.00013

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