Disease relevance of oxazolidine

• Mode of mutagenic action for the biocide Bioban CS-1246 in mouse lymphoma cells and implications for its in vivo mutagenic potential [1].
• The solid phase synthesis of a set of peptide aldehydes derived from the NS5A/NS5B junction of hepatitis C virus (HCV) viral polyprotein is demonstrated using an oxazolidine linker and the Multipin method [2].
• The oxazolidine synthesized from (-) ephedrine and butyraldehyde caused greatest hyperthermia [3].

High impact information on oxazolidine

• In the present study, we investigate the consequences of acidifying the cytosol using the weak acid, 5', 5"-dimethyl oxazolidine 2,4-dione (DMO) [4].
• Spin-labeled long-chain (m,n)acyl-CoA's (general formula: CH3(CH2)mCR(CH2)nCOSCoA, where R is an oxazolidine ring containing a nitroxide) inhibit anion transports through the inner mitochondrial membrane at low concentrations as ordinary long-chain acyl-CoA's do [5].
• Union of the two fragments 9 and 10 via oxazolidine intermediate afforded amino nitrile 39, which upon esterification of the primary alcohol with (R)-N-(S-4,4',4' '-trimethoxyltrityl) Cys (42) afforded 43 [6].
• The efficient Fmoc solid-phase peptide synthesis of the 37-residue human Amylin and its amyloidogenic 8-37 fragment was achieved using pseudoproline (oxazolidine) dipeptide derivatives [7].
• Nucleophilic addition of lithiated TBS-protected propargylic ethers 25 and 32 to l-serine-derived aldehyde 26, respectively, afforded oxazolidine intermediates 27 and 33 [8].

Chemical compound and disease context of oxazolidine

• The biocidal agent, BIOBAN CS-1246 (7-ethyl bicyclooxazolidine, CAS# 7747-35-5, CS-1246) induced a concentration-dependent mutagenic response in mouse lymphoma (L5178Y TK+/-) cells both with and without the addition of S9 metabolic activation [1].

Biological context of oxazolidine

• The syntheses of analogues 2 and 3 from ketones 13 and 20, respectively, were completed by the following sequence of reactions: diastereoselective reduction (NaBH(4)/CeCl(3) or DIBAL-H), hydrolysis of the oxazolidine ring, liberation of the amino group, and installation of the N-amide group [9].
• They showed that a mode of action, involving opening of the oxazolidine ring to give an iminium ion, followed by initial noncovalent binding in the minor groove and subsequent alkylation of the 2-amino group of guanine, was rational and attended by favorable interaction energies in each step [10].
• Primary studies of the structure-activity relationships for inhibition of PAF-induced aggregation showed that the oxygen substitution at the C-15 position and the presence of an oxazolidine ring in spiramine alkaloids were essential to their antiplatelet aggregation effects [11].
• The effect of hydroxypropyl-beta-cyclodextrin on the kinetics of hydrolysis of an oxazolidine prodrug [12].
• Mass spectral experiments under atmospheric pressure chemical ionization and electrospray ionization-ion trap conditions showed formation of imine metabolites (and/or oxazolidine from 7) as well as products of N-dealkylation and aromatic hydroxylation when the secondary amine substrates were incubated with rat liver microsomes or CYP1A2 [13].

Anatomical context of oxazolidine

• Effects of KST48 [(2R,5SR)3-(2-chlorobenzoyl)-5-(4-chlorophenoxymethyl)-2(3,4-dichlorophenyl) oxazolidine] on glucose transport in L6 myocytes [14].
• Some of 1,3-oxazolidine compounds possessing acetyl and 3',4'-dichlorophenyl group displayed strong inhibitory activities on Fc epsilonRI-mediated mast cell degranulation, suggesting that they can be used as lead compounds for the development of anti-allergic agents [15].
• Electron paramagnetic resonance (EPR) and differential scanning calorimetry (DSC) have been used to study the effect on the phase transition of dimyristoylphosphatidylcholine membranes of incorporating various stearic acid spin labels (SASL's) that contain the bulky oxazolidine ring at various positions along the stearyl chain [16].

Associations of oxazolidine with other chemical compounds

• The present study focuses on the kinetics and mechanisms of the reactions of piperidine, pyrrolidine and oxazolidine nitroxides with HO2*/O2*-, *NO2 and CO3*- radicals, which are key intermediates in many inflammatory and degenerative diseases [17].
• However, we could not enhance the inhibitory activity against iNOS by introducing an alkyl substituent into the 2-aminothiazole ring as we could in the case of oxazolidine one [18].
• Thus, treatment of compound 19 with HCHO in the presence of catalytic amount of pTsOH followed by reduction (NaBH3CN, TFA, CH2Cl2) of the so-formed oxazolidine 24 gave the N-methylated product 25 [19].
• Open D-ring galanthamine analogues were prepared using ring-opening reactions of the quaternarized urethane or oxazolidine functions and were evaluated for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition potency [20].

Gene context of oxazolidine

• Recently, we reported that the 2-imino-1,3-oxazolidine (1a) weakly inhibits iNOS and that introduction of an alkyl moiety on the oxazolidine ring of 1a enhances the inhibitory activity and selectivity for iNOS [18].
• We found that a tetrahedral intermediate can be stabilized by the formation of an oxazolidine ring with the nonscissile P2-P1 peptide bond [21].
• The separation of oxazolidine derivatives 2 and 3 diastereomers were achieved with a C18 column but the compounds underwent in-column hydrolysis to give (-)- and (+)-1, respectively [22].
• Versatility of oxazolidine spin labels--a model study with acyl-alpha-chymotrypsin [23].

Analytical, diagnostic and therapeutic context of oxazolidine

• Determination of acrolein in air as an oxazolidine derivative by gas chromatography [24].
• The three first DNPH samplers are to be analyzed by HPLC and the latter by GC-MS for the oxazolidine derivatives [25].

References