Oxazolidinone: Search for Highly Potent Antibacterial.

Lohray, B. B.; Lohray, Vidya B.; Srivastava, B.; Gupta, Sunil; Solanki, Manish; Kapadnis, Prashant B.; Takale, Vijay; Pandya, Purvi

doi:10.1002/chin.200439114

Cited by 5 publications

(7 citation statements)

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“…Compound 93 has been found to have excellent activity against a panel of Gram-positive strains with MIC values in the range of 0.25-1.0 μg/mL [92]. Substitution on the para-position of the phenacyl group with 4-methoxyl or 4-acetamido groups improved antibacterial activities for some Gram-positive strains tested.…”

Section: B and C Ring Modificationsmentioning

confidence: 98%

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Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

Wang¹

2008

AIAMC

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Oxazolidinones are important synthetic antibacterial agents useful for the treatment of multi antibiotic resistant Gram-positive bacterial infections. Since the launch of Linezolid, the first member of the oxazolidinone antibacterial family, there have been many studies directed towards structural optimization and the development of second generation oxazolidinones. The N-aryl 5-acetamido methyl oxazolidinone is the core structure for this class of antibacterial agents and the oxazolidinone component is essential for antibacterial activities. The chiral cyclic carbamate 5-hydroxymethyloxazolidin-2-one and 6-hydroxymethyl-[1,3]oxazinan-2-one are also important building blocks for synthesizing other biologically active compounds. Because of the importance of these compounds, many methods have been developed for their facile syntheses. In the first part of this paper, the synthesis of Linezolid and its analogs, as well as the preparation of the oxazolidinone core structures, will be reviewed. Secondly, recent developments in the area of oxazolidinone antibacterial agents including structure-activity relationships will be reviewed.

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Section: B and C Ring Modificationsmentioning

confidence: 98%

“…These compounds (87)(88)(89)(90) A series of arylcarbonyl and arylsulfonyl oxazolidinones have also been synthesized and evaluated (91,92). Many of these compounds showed superior in vitro antibacterial activity for Gram-positive bacteria over Linezolid.…”

Section: B and C Ring Modificationsmentioning

confidence: 99%

Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

Wang¹

2008

AIAMC

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“…The incorporation of piperazine is an important synthetic strategy in drug discovery due to its easy modificability, proper alkality, water solubility, the capacity for the formation of hydrogen bonds and adjustment of molecular physicochemical properties. 4,5 A broad range of biological active compounds displaying antibacterial, 3,[6][7][8] antifungal, 9,10 anticancer, [11][12][13] antiparasitic, 14,15 antihistamin, 16 psychotolytic, 17 and antidepressive activities 18 have been also found to contain this versatile core. In particular, structurally simple 1-(1-naphthylmethyl)-piperazine, as the efflux pump inhibitor, could exert positive effect on tetracyclines and ciprofloxacin against their resistant bacteria.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Azole-containing Piperazine Derivatives and Evaluation of their Antibacterial, Antifungal and Cytotoxic Activities

Gan¹,

Fang²,

Zhou³

2010

Bulletin of the Korean Chemical Society

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A series of azole-containing piperazine derivatives have been designed and synthesized. The obtained compounds were investigated in vitro for their antibacterial, antifungal and cytotoxic activities. The preliminary results showed that most compounds exhibited moderate to significant antibacterial and antifungal activities in vitro. 1-(4-((4-chlorophenyl) (phenyl)methyl)piperazin-1-yl)-2-(1H-imidazol-1-yl)ethanone and 1-(4-((4-Chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-(2-phenyl-1H-imidazol-1-yl)ethanone gave remarkable and broad-spectrum antimicrobial efficacy against all tested strains with MIC values ranging from 3.1 to 25 μg/mL, and exhibited comparable activities to the standard drugs chloramphenicol and fluconazole in clinic. Moreover, 2-((4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)methyl)-1H-benzo [d]imidazole was found to be the most effective in vitro against the PC-3 cell line, reaching growth inhibition values (36.4, 60.1 and 76.5%) for each tested concentration: 25 μM, 50 μΜ and 100 μM in dose-dependent manner. The results also showed that the azole ring had noticeable effect on their antimicrobial and cytotoxic activities, and imidazole and benzimidazole moiety were much more favourable to biological activity than 1,2,4-triazole.

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“…15 Recently, Gorobets and co-workers described a new facile protocol for the synthesis of aromatic and heteroaromatic 3-acylacrylic acids 9 in good yields (54-78%). 16 Aromatic ketones 7, glyoxylic acid monohydrate 8, and Yb(OTf) 3 (2.5 mol%) are reacted under microwave irradiation.…”

Section: Introductionmentioning

confidence: 99%