724793-80-0

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-[[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-5-oxazolidinyl]Methyl]-
• Synonyms: 1H-Isoindole-1,3(2H)-dione, 2-[[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-5-oxazolidinyl]Methyl]-;(S)-2-((3-(3-fluoro-4-iodophenyl)-2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione
• CAS NO: 724793-80-0
• Molecular Formula: C₁₈H₁₂FIN₂O₄
• Molecular Weight: 466.2017532
• Mol File: 724793-80-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-[[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-5-oxazolidinyl]Methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-[[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-5-oxazolidinyl]Methyl]-(724793-80-0)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-[[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-5-oxazolidinyl]Methyl]-(724793-80-0)

Safety Data

• Hazardous Substances Data: 724793-80-0(Hazardous Substances Data)

Usage

Core structure

1H-isoindole-1,3(2H)-dione
A heterocyclic aromatic core with a fused benzene ring and an isoindole moiety.

Functional group

2-[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-5-oxazolidinyl]methyl
A complex side chain attached to the core structure, which includes various functional groups.
3. Heterocyclic and aromatic moieties
The compound contains both heterocyclic (containing atoms other than carbon, such as nitrogen or oxygen) and aromatic (planar, conjugated, and cyclic) structures, which may contribute to its pharmacological and biological activities.
4. Potential pharmacological and biological activities
The presence of various functional groups in the molecule suggests that it may have potential pharmacological and biological activities, which could be explored in drug discovery and development.
5. 3-fluoro-4-iodophenyl group
This specific functional group in the molecule may contribute to its potential applications in medicinal chemistry, as it can influence the compound's properties and interactions with biological targets.
6. Oxazolidinylmethyl group
The presence of this group in the molecule may indicate potential reactivity or interaction with biological systems, which could be relevant for its potential applications in drug discovery and development.
7. Applications in drug discovery and development
The compound's unique structure and potential pharmacological and biological activities make it a promising candidate for further studies in drug discovery and development.
8. Relevance to materials science and chemical synthesis
The compound's structure and properties may also be of interest in materials science and chemical synthesis, as it could potentially be used as a building block or precursor for other complex molecules or materials.

Upstream product

• 487041-08-7 (5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one 
• 149524-42-5 (5R)-3-(3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one 
• 149524-47-0 N-(carbobenzyloxy)-3-fluoroaniline 
• 372-19-0 meta-fluoroaniline 
• 501939-82-8 (5R)-methanesulfonic acid 3-(3-fluoro-4-iodophenyl)-2-oxo-oxazolidin-5-ylmethyl ester 
• 1074-82-4 potassium phtalimide 

Downstream Products

• 627543-03-7 (5S)-5-aminomethyl-3-(3-fluoro-4-iodophenyl)-oxazolidin-2-one 
• 916888-22-7 (5S)-N-{3-[2-fluoro-4'-({[1-(4-methoxybenzyl)-1H-[1,2,3]triazol-5-ylmethyl]amino}methyl)biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}acetamide hydrochloride 
• 916888-19-2 (5S)-{4'-[5-(acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2'-fluorobiphenyl-4-ylmethyl}-[1-(4-methoxybenzyl)-1H-[1,2,3 ]triazol-4-ylmethyl]carbamic acid tert-butyl ester 
• 149524-45-8 (S)-N-[3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidine-5-ylmethyl]acetamide 

Relevant articles and documents

Compound design guidelines for evading the efflux and permeation barriers of Escherichia coli with the oxazolidinone class of antibacterials: Test case for a general approach to improving whole cell Gram-negative activity

Previously we reported the results from an effort to improve Gram-negative antibacterial activity in the oxazolidinone class of antibiotics via a systematic medicinal chemistry campaign focused entirely on C-ring modifications. In that series we set about testing if the efflux and permeation barriers intrinsic to the outer membrane of Escherichia coli could be rationally overcome by designing analogs to reside in specific property limits associated with Gram-negative activity: i) low MW (7.4 1), and iii) zwitterionic character at pH 7.4. Indeed, we observed that only analogs residing within these limits were able to overcome these barriers. Herein we report the results from a parallel effort where we explored structural changes throughout all three rings in the scaffold for the same purpose. Compounds were tested against a diagnostic MIC panel of Escherichia coli and Staphylococcus aureus strains to determine the impact of combining structural modifications in overcoming the OM barriers and in bridging the potency gap between the species. The results demonstrated that distributing the charge-carrying moieties across two rings was also beneficial for avoidance of the outer membrane barriers. Importantly, analysis of the structure-permeation relationship (SPR) obtained from this and the prior study indicated that in addition to MW, polarity, and zwitterionic character, having ≤4 rotatable bonds is also associated with evasion of the OM barriers. These combined results provide the medicinal chemist with a framework and strategy for overcoming the OM barriers in GNB in antibacterial drug discovery efforts.

TOPICAL FORMULATIONS OF BIARYL HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF

The present invention relates to topical formulations of biaryl heterocyclic compounds and methods of use thereof for treating acne and other skin infections caused or mediated by Streptococcus pyogenes, Streptococcus agalactiae, Haemophilus influenza, Trichomonas vaginalis, Klebsiella sp., Enterobacter sp., Proteus sp., Propionibacterium acnes, Gardnerella vaginalis, or Staphylococcus aureus (including Methicillin-resistant Staphylococcus aureus (MRSA)) in a patient in need thereof. In certain embodiments, the acne or other skin infection is caused or mediated by Propionibacterium acnes, Gardnerella vaginalis, or Staphylococcus aureus.

Process for the synthesis of triazoles

The present invention relates to processes for the preparation of triazoles. These compounds are useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents.