97859-49-9

Basic information

• Product Name: (R)-5-(hydroxyMethyl)oxazolidin-2-one
• Synonyms: (R)-5-(hydroxyMethyl)oxazolidin-2-one;(5R)-5-(Hydroxymethyl)-1,3-oxazolidin-2-one;(R)-5-Hydroxymethyl-2-oxazolidinone
• CAS NO: 97859-49-9
• Molecular Formula: C₄H₇NO₃
• Molecular Weight: 117.10328
• Mol File: 97859-49-9.mol
• Article Data: 17

Chemical Properties

• Melting Point: 93.0℃ (isopropanol )
• Appearance: /
• CAS DataBase Reference: (R)-5-(hydroxyMethyl)oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-(hydroxyMethyl)oxazolidin-2-one(97859-49-9)
• EPA Substance Registry System: (R)-5-(hydroxyMethyl)oxazolidin-2-one(97859-49-9)

Safety Data

• Hazardous Substances Data: 97859-49-9(Hazardous Substances Data)

Usage

General Description

(R)-5-(hydroxymethyl)oxazolidin-2-one, also known as (R)-PZQ, is a chemical compound with the molecular formula C4H7NO3. It is a chiral oxazolidinone derivative commonly used as a building block in organic synthesis. The compound has a five-membered ring structure with an oxazolidinone group and a hydroxymethyl group attached to the carbon atom. It is a white solid that is soluble in polar organic solvents. (R)-PZQ has been utilized in the synthesis of various pharmaceuticals and biologically active compounds due to its versatile reactivity and structural properties. It also serves as a key intermediate in the production of agrochemicals and fine chemicals.

Upstream product

• 113420-80-7 Acetic acid (S)-2-oxo-oxazolidin-5-ylmethyl ester 
• 112663-80-6 (S)-2-oxazolidinone-5-carboxylic acid benzyl ester 
• 61278-21-5 (S)-3-Amino-1,2-propanediol 
• 105-58-8 Diethyl carbonate 
• 7517-99-9 5-hydroxymethyl-2-oxazolidinone 
• 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 
• 113420-80-7 Acetic acid (R)-2-oxo-oxazolidin-5-ylmethyl ester 
• 169048-84-4 (R)-2-oxo-oxazolidine-5-carboxylic acid benzyl ester 
• 66211-46-9 (R)-3-amino-1,2-propanediol 
• 274264-54-9 (5R)-5-[(benzyloxy)methyl]-1,3-oxazolidin-2-one 
• 641617-22-3 (R)-3-[N-(benzyloxycarbonyl)amino]-1,2-propanediol 

Downstream Products

• 352524-57-3 (R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)oxazolidin-2-one 
• 402718-20-1 ((5R)-2-oxo-1,3-oxazolidin-5-yl)methyl 2-nitrobenzenesulfonate 
• 109794-69-6 (R)-(2-oxo-1,3-oxazolidin-5-yl)methyl 4-methylbenzenesulfonate 
• 109794-68-5 (S)-(2-oxo-1,3-oxazolidin-5-yl)methyl 4-methylbenzenesulfonate 

Relevant articles and documents

MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS

Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidases SpsB and/or LepB, an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

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.

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

Compounds of formula (I), pharmaceutically acceptable salts thereof, and uses of the compounds of formula (I) for treating bacterial infections are disclosed.