60487-07-2

Upstream product

• 61278-21-5 (S)-3-Amino-1,2-propanediol 
• 105-58-8 Diethyl carbonate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 852805-35-7 (S)-5-(4-methoxyphenoxymethyl)-1,3-oxazolidin-2-one 
• 330555-60-7 (S)-5-triphenylmethoxymethyl-1,3-oxazolidin-2-one 
• 7517-99-9 5-hydroxymethyl-2-oxazolidinone 
• 112663-80-6 (S)-2-oxazolidinone-5-carboxylic acid benzyl ester 
• 113420-80-7 Acetic acid (S)-2-oxo-oxazolidin-5-ylmethyl ester 

Downstream Products

• 109794-68-5 (S)-(2-oxo-1,3-oxazolidin-5-yl)methyl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

Resolution of 5-hydroxymethyl-2-oxazolidinone by preferential crystallization and investigations on the nature of the racemates of some 2-oxazolidinone derivatives

After ascertaining its conglomerate nature by DSC and solid-state IR analyses, 5-hydroxymethyl-2-oxazolidinone 1, whose enantiomers are very important synthons, was efficiently resolved without chiral auxiliaries by preferential crystallization from a supersaturated isopropanolic solution of the racemate, slightly enriched in one enantiomer (3.7% ee). Favourable conditions to the entrainment were defined utilizing the previously constructed ternary phase diagram {(R)-1, (S)-1, 2-propanol}. Furthermore, the investigations were extended to other chiral 2-oxazolidinones with a functionalized methyl at the 5- or 4-position finding that 5-tosyloxymethyl-2-oxazolidinone is a racemic compound, whereas just the corresponding mesylate is a conglomerate as the parent alcohol 1. Interestingly, 4-hydroxymethyl-2-oxazolidinone 4 proved to be a racemic compound in contrast with its positional isomer 1 demonstrating how a relatively fine variation in the molecular structure can unpredictably influence the crystalline nature of the racemate. The X-ray structure determination carried out on (S)-(+)-1, (±)-4 and (R)-(+)-4 enlightened the importance of the hydrogen bond in determining different supramolecular assembling in the two homochiral compounds with respect to the racemic one and allowed a correlation with the stability of the crystal to be made.

PREPARATION AND APPLICATION OF A CHIRAL C3-BUILDING BLOCK FOR AMINO ALCOHOL SYNTHESIS BY BAKERS' YEAST REDUCTION OF 1-ACYLOXY-3-AZIDO-2-PROPANONE

Bakers' yeast-mediated reduction of 1-acyloxy-3-azido-2-propanone gives (S)-1-acyloxy-3-azido-2-propanol with high enantiomeric excess, which is a useful chiral C3-building block for amino alcohols such as β-blockers.

Inhibition of 3-phosphoglycerate dehydrogenase (PHGDH) by indole amides abrogates de novo serine synthesis in cancer cells

Cancer cells reprogram their metabolism to support growth and to mitigate cellular stressors. The serine synthesis pathway has been identified as a metabolic pathway frequently altered in cancers and there has been considerable interest in developing pharmacological agents to target this pathway. Here, we report a series of indole amides that inhibit human 3-phosphoglycerate dehydrogenase (PHGDH), the enzyme that catalyzes the first committed step of the serine synthesis pathway. Using X-ray crystallography, we show that the indole amides bind the NAD+ pocket of PHGDH. Through structure-based optimization we were able to develop compounds with low nanomolar affinities for PHGDH in an enzymatic IC50 assay. In cellular assays, the most potent compounds inhibited de novo serine synthesis with low micromolar to sub-micromolar activities and these compounds successfully abrogated the proliferation of cancer cells in serine free media. The indole amide series reported here represent an important improvement over previously published PHGDH inhibitors as they are markedly more potent and their mechanism of action is better defined.

QUINAZOLINE COMPOUND FOR EGFR INHIBITION

Disclosed is a novel quinazoline compound. Specifically, disclosed are a compound represented by the formula (I) and a pharmacologically acceptable salt.

Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB

Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified cera

New chemoenzymatic pathway for β-adrenergic blocking agents

The lipase mediated kinetic resolution of pharmaceutically important β-hydroxy nitriles is described in high enantiomeric excesses and good yields. Some of the chiral β-hydroxy nitriles have been employed in the synthesis of β-adrenergic blocking agents such as propranolol, alprenolol and moprolol. This protocol has also been extended for the enantiopure preparation of 5-(4-tosyloxymethyl)-1,3-oxazolidine-2-one and 3-hydroxy-4-tosyloxybutanenitrile, chiral intermediates of high synthetic value.

OXAZOLIDINONE DERIVATIVES N-SUBSTITUTED BY A BICYCLIC RING, FOR USE AS ANTIBACTERIAL AGENTS

Compounds of formula (I) and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula (I) as well as pharmaceutically acceptable compositions comprising compounds of formula (I). Compoun

Synthesis and antibacterial evaluation of oxazolidin-2-ones structurally related to linezolid

Compounds structurally related to the known antimicrobial drug linezolid were selected in order to evaluate the influence of electron-withdrawing properties and altered geometric features as a result of the N-substituent modification. After a preliminary

Efficient Pathways to (R)- and (S)-5-Hydroxymethyl-2-oxazolidinone and some Derivatives

2-Oxazolidinones are a very interesting class of compounds due to their various pharmacological effects.Two new syntheses of enantiomerically pure (R)- and (S)-5-hydroxymethyl-2-oxazolidinone have been developed starting with D-mannitol, L-ascorbic acid and (R)- or (S)-malic acid. (R)- and (S)-5-hydroxymethyl-2-oxazolidinone have been used to synthesize some new homochiral 2-oxazolidinone derivatives.

AN EFFICIENT SYNTHESIS OF (R)-(+)- AND (S)-(-)-PROPRANOLOL FROM RESOLVED 5-IODOMETHYLOXAZOLIDIN-2-ONES

(1'S*,5S,R)-3-(1'-phenyleth-1'-yl)-5-iodomethyloxazolidin-2-ones, 4a,b, have been synthesized and easily resolved by silica gel chromatography.Each pure diastereomer has been then converted to (S)-(-)-propranolol 1a and (R)-(+)-propranolol 1b, respectively.An empirical correlation of configuration and 1H NMR chemical shift for alternate diastereomers has been devised and has proved to be applicable in assigning the configuration of 5-substituted 3-(1'-phenyleth-1'-yl)oxazolidin-2-ones.