Synthesis and antibacterial activities of chiral 1,3-oxazinan-2-one derivatives

Wang, Guijun; Ella‐Menye, Jean‐Rene; Sharma, Vibha

doi:10.1016/j.bmcl.2006.01.072

Cited by 43 publications

(36 citation statements)

References 19 publications

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“…Cyclic urethanes are well known for their biological/pharmacological properties, like the title compound which is of current interest in the syntheses of pharmaceutical compounds and 1,3-amino alcohols [1][2][3][4]. Carbamate group p-electron delocalization makes the six-membered urethane ring rather flat (only C3 deviates significantly, by 0.72 Å, from least-squares plane defined by the carbamate group).…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 3-cyclohexyl-1,3-oxazinan-2-one, C10H17NO2

Miltojević¹,

Radulović²,

Vukićević³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 3-cyclohexyl-1,3-oxazinan-2-one, C10H17NO2

Miltojević¹,

Radulović²,

Vukićević³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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“…For example, compounds 128-130 were found to have MICs against S. aureus at 10-30 μg/mL and B. sutilis at 8-30 μg/mL concentrations [29]. These compounds can be further optimized to be more potent against Gram-positive or Gramnegative bacteria.…”

Section: Other Oxazolidinone Related Antibacterial Agentsmentioning

confidence: 97%

“…Future structure optimization and assessment of the mode of action can help the design of new potent antibacterial agents. Another novel system that has been reported recently is a tertiary amine composed of 6-aminomethyl 1,3-oxazinan-2-one or oxazolidinone and two aromatic substituents (126-127) [29]. In this system, three sites can be modified for structure optimization.…”

Section: Other Oxazolidinone Related Antibacterial Agentsmentioning

confidence: 99%

“…The 5-S-aminomethyl 2-oxazolidinone (32) is the core structure in antibacterial agents such as Linezolid (1). The 6-membered ring 1,3-oxazinan-2-one derivatives (33,34) also exhibit biological activities such as anti-inflammatory [28], and antibacterial activities [29].…”

Section: Synthesis Of the 5-hydroxyl Methyl Oxazolidinone Core Structurementioning

confidence: 99%

“…Chiral 5-substituted 2-oxazolidinones (31,32) and the analogous 6-substituted 1,3-oxazinan-2-ones (33, 34) are useful intermediates for synthesizing many biologically active compounds [27][28][29]. The 5-S-aminomethyl 2-oxazolidinone (32) is the core structure in antibacterial agents such as Linezolid (1).…”

Section: Synthesis Of the 5-hydroxyl Methyl Oxazolidinone Core Structurementioning

confidence: 99%

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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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Tin‐Catalyzed Selective Reductive Hydroamination of Alkynes for the Synthesis of Tertiary Amines

et al. 2016

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Au niquep reference of tin(II) for aniline activation is disclosed. In the present workt in(II) triflate-catalyzedh ighly selective Markovnikov reductive hydroaminationo fi nternala sw ell as terminal alkynes is reported. Them echanistic study revealed the involvement of twos teps in one pot wherein alkyne reducest oc orresponding alkene in presence of PMHS as reducing agent followed by hydroamina-tion of alkene.Abroad range of alkynes transformed into tertiary amines with good to excellent yield. This method is equally applicablei ns ynthesis of secondary amines.

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Synthesis and antibacterial activities of chiral 1,3-oxazinan-2-one derivatives

Cited by 43 publications

References 19 publications

Crystal structure of 3-cyclohexyl-1,3-oxazinan-2-one, C10H17NO2

Crystal structure of 3-cyclohexyl-1,3-oxazinan-2-one, C10H17NO2

Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

Tin‐Catalyzed Selective Reductive Hydroamination of Alkynes for the Synthesis of Tertiary Amines

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