N-Halo Derivatives VI: Microbiological and Chemical Evaluations of 3-Chloro-2-oxazolidinones

Kosugi, Masanori; Kaminski, James J.; Selk, Sally H.; Pitman, Ian H.; Higuchi, Takeru; Bodor, Nicolae

doi:10.1002/jps.2600651212

Cited by 36 publications

(10 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…N -Halo-2-oxazolidinones [1,2] form polymers that can be used as coatings on plastics, glass and synthetic fibres [3], and the monomers can be used as disinfectants [4][5][6][7][8][9]. Although certain organisms are quite resistant to the most thoroughly studied chloro compound, 3-chloro-4,4-dimethyl-2-oxazolidinone [10] does have advantages as an auxiliary biocide, especially for disinfection of minor water supplies: it is an easily stored powder, and its relative stability ensures sustained action.…”

Section: Introductionmentioning

confidence: 99%

Kinetics of N‐bromination of 2‐oxazolidinone

Amoedo

Antelo

Arce

et al. 2004

Int J of Chemical Kinetics

View full text Add to dashboard Cite

The kinetics of N-bromination of 2-oxazolidinone by transfer of Br from sodium hypobromite, N-bromosuccinimide (NBS), or N-bromoacetamide (NBA) were determined spectrophotometrically, at pH between 4.6 and 12.45 (depending on the brominating agent). The reaction with hypobromite was of first order with respect to both the hypobromite and the substrate. The bromination of oxazolidinone with NBS (or NBA) has been found to be a reversible process of order one with respect to both NBA (or NBA) and oxazolidinone in the forward direction, and order one with respect to SI (or ACAM) and the resulting N-bromo-oxazolidinone in the other. The pH dependence of the reaction rate was in keeping with a mechanism in which all the brominating agents (HOBr, BrO − , NBS and NBA) react predominantly with the anion of the substrate. Bimolecular bromination rate constants increased in the order BrO − < NBA <

show abstract

Section: Introductionmentioning

confidence: 99%

Kinetics of N‐bromination of 2‐oxazolidinone

Amoedo

Antelo

Arce

et al. 2004

Int J of Chemical Kinetics

View full text Add to dashboard Cite

show abstract

“…After establishing the mechanism of their decomposition [385], it was realized that stable N-chloramines that have much lower "chlorine potential" and are much less corrosive could be obtained if the a-carbons lack hydrogen [385][386][387][388]. Structures 174-176 in Fig.…”

Section: Activated Soft Drugsmentioning

confidence: 99%

Retrometabolism‐Based Drug Design and Targeting

Bodor

Buchwald

2010

Burger's Medicinal Chemistry and Drug Discovery

View full text Add to dashboard Cite

Retrometabolic drug design (RMDD) approaches are systematic methodologies aimed to design safe compounds with an improved therapeutic index. RMDDs thoroughly integrate structure– activity and structure‐metabolism considerations into the entire design process and incorporate two major concepts aimed to design soft drugs and chemical delivery systems, respectively. Soft drugs (SDs) are new, active therapeutic agents designed to undergo predictable metabolism resulting in inactive metabolites after exerting their desired therapeutic effect(s). Chemical delivery systems (CDSs) are biologically inert molecules that provide enhanced and targeted delivery of an active drug to a particular organ or site through a designed sequential metabolism that involves several steps. Here, we present a comprehensive review including a general overview of the RMDD principles and a large number of specific examples from various pharmacological areas, including many recent developments, to illustrate RMDD concepts. Whenever possible, the rationale for the design as well as the pharmacokinetic and pharmacodynamic properties of the new therapeutic agents are briefly summarized and compared to those of the other compounds used in the same field.

show abstract

“…Agent I was first prepared and Agent I and shown to be bactericidal by Kaminski and co-workers (4,5). Recent experiments in these laboratories have demonstrated that Agent I is an effective bactericide in a laboratory water treatment plant (6), that Agent I is exceptionally stable in water and in dry storage (7), that "Agent I eradicates a broad spectrum of bacteria in water (8), and that Agent I is apparently nontoxic to chickens drinking water containing 4 .…”

Section: List Of Tablesmentioning

confidence: 99%