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(5R)-3-(3-FLUORO-4-IODOPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE is a chemical compound belonging to the oxazolidinone family, characterized by its anti-bacterial properties and a unique molecular structure that includes iodine and fluorine elements attached to a phenyl group. This structure is believed to influence its reactivity and potential applications in the synthesis of bioactive molecules or pharmaceutical drugs.

487041-08-7

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  • (5R)-3-(3-fluoro-4-iodophenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one

    Cas No: 487041-08-7

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487041-08-7 Usage

Uses

Used in Pharmaceutical Industry:
(5R)-3-(3-FLUORO-4-IODOPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE is used as a potential anti-bacterial agent for its broad-spectrum coverage against both Gram-positive and Gram-negative bacteria. Its specific molecular structure, with iodine and fluorine elements, suggests that it could be a candidate for the development of new antibiotics, especially in the context of increasing antibiotic resistance.
Used in Chemical Synthesis:
(5R)-3-(3-FLUORO-4-IODOPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE is used as a building block in the synthesis of bioactive molecules. Its unique structure may allow for the creation of new compounds with specific biological activities, which could be explored in various fields such as medicine, agriculture, or materials science.

Check Digit Verification of cas no

The CAS Registry Mumber 487041-08-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,8,7,0,4 and 1 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 487041-08:
(8*4)+(7*8)+(6*7)+(5*0)+(4*4)+(3*1)+(2*0)+(1*8)=157
157 % 10 = 7
So 487041-08-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H9FINO3/c11-8-3-6(1-2-9(8)12)13-4-7(5-14)16-10(13)15/h1-3,7,14H,4-5H2/t7-/m1/s1

487041-08-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name (5R)-3-(3-FLUORO-4-IODOPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE

1.2 Other means of identification

Product number -
Other names P-MENTHA-1,5-DIENE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:487041-08-7 SDS

487041-08-7Relevant 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

Spaulding, Andrew,Takrouri, Khuloud,Mahalingam, Pornachandran,Cleary, Dillon C.,Cooper, Harold D.,Zucchi, Paola,Tear, Westley,Koleva, Bilyana,Beuning, Penny J.,Hirsch, Elizabeth B.,Aggen, James B.

, p. 5310 - 5321 (2017/11/13)

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

-

, (2017/12/15)

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.

Method for preparing tedizolid phosphate

-

, (2016/12/01)

The invention relates to the technical field of preparation of tedizolid phosphate, and especially relates to a preparation method of tedizolid phosphate. According to the invention, 3-fluoroaniline is taken as a raw material, and is subjected to a nucleophilic substitution reaction with (R)-(-)-glycidyl butyrate, then a cyclization reaction and hydrolysis are carried out, protective group is removed to obtain a compound (VI); the compound (VI) is subjected to an iodination reaction and the nucleophilic substitution reaction to obtain a compound (VIII); the compound (VIII) and 2-(1-methyl-tetrazolium-5-group)-5-bromopyridine (IX) are reacted, and then a target product (I) is obtained with phosphoric acid. The method has the advantages of short route, mild reaction condition, and easy post-treatment, and is more suitable for industrial production requirement.

A PROCESS FOR THE PREPARATION OF TEDIZOLID PHOSPHATE

-

, (2016/06/28)

The present invention provides a process for the preparation of tedizolid phosphate.

METHOD FOR TREATING, PREVENTING, OR REDUCING THE RISK OF SKIN INFECTION

-

, (2016/06/06)

The present invention relates to methods for treating acne and other skin infections caused or mediated by Propionibacterium acnes, Gardnerella vaginalis, or Staphylococcus aureus in a patient with a safe and effective amount of a topically applied oxazolidinone antibiotic compound.

An improved efficient synthesis of the antibacterial agent torezolid

Li, Gang,Yuan, Bao-Kun,Tang, Wu,Zhao, Hong-Yi,Lin, Zi-Yun,Huang, Hai-Hong

, p. 143 - 146 (2015/02/19)

An improved and efficient method for the preparation of torezolid based on Suzuki cross-coupling reaction as the key step was developed on a gram scale in five steps. The total yield was 44% and the optical purity of torezolid by the improved method was above 99%.

Discovery of torezolid as a novel 5-hydroxymethyl-oxazolidinone antibacterial agent

Im, Weon Bin,Choi, Sun Ho,Park, Ju-Young,Choi, Sung Hak,Finn, John,Yoon, Sung-Hwa

, p. 1027 - 1039 (2011/04/17)

A series of novel substituted pyridyl phenyl oxazolidinone analogues were synthesized and their structure-activity relationship (SAR) was investigated based on in vitro and in vivo antibacterial activities. The minimum inhibitory concentrations (MICs) of the synthesized compounds against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) ranged from 0.12 to 2.0 μg/mL, and against Haemophilus influenzae (Hi) from 2.0 to 8.0 μg/mL. Compared to linezolid, only four compounds (11, 12, 21 and 29) showed higher in vitro antibacterial activities and better in vivo protective effects in mice. To improve the aqueous solubility, various prodrugs of compound 11 (DA-7157), which exerted a potency that was enhanced by 2-8-fold compared to that of linezolid, were synthesized. Among the prodrugs, the phosphate compound 42 exhibited excellent aqueous solubility (>50 mg/mL in DW) and good pharmacokinetic profiles, along with better in vivo efficacy than linezolid. This compound 42 is currently undergoing clinical trials with the brand name Torezolid.

Process for the synthesis of triazoles

-

Page/Page column 37, (2010/09/18)

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.

Antibacterial oxazolidinones possessing a novel C-5 side chain. (5R)-trans-3-[3-fluoro-4-(1-oxotetrahydrothiopyran-4-yl)phenyl] -2-oxooxazolidine-5-carboxylic acid amide (PF-00422602), a new lead compound

Poel, Toni-Jo,Thomas, Richard C.,Adams, Wade J.,Aristoff, Paul A.,Barbachyn, Michael R.,Boyer, Frederick E.,Brieland, Joan,Brideau, Roger,Brodfuehrer, Joanne,Brown, Alan P.,Choy, Allison L.,Dermyer, Michael,Dority, Michael,Ford, Charles W.,Gadwood, Robert C.,Hanna, Debra,Hongliang, Cai,Huband, Michael D.,Huber, Christopher,Kelly, Rose,Kim, Ji-Young,Martin Jr., Joseph P.,Pagano, Paul J.,Ross, Daniel,Skerlos, Laura,Sulavik, Mark C.,Zhu, Tong,Zurenko, Gary E.,Vara Prasad

, p. 5886 - 5889 (2008/04/05)

Oxazolidinones possessing a C-5 carboxamide functionality (reverse amides) represent a new series of compounds that block bacterial protein synthesis. These reverse amides also exhibited less potency against monoamine oxidase (MAO) enzymes and thus posses

Novel substituted (pyridin-3-yl)phenyloxazolidinones: Antibacterial agents with reduced activity against monoamine oxidase A and increased solubility

Reck, Folkert,Zhou, Fei,Eyermann, Charles J.,Kern, Gunther,Carcanague, Dan,Ioannidis, Georgine,Illingworth, Ruth,Poon, Grace,Gravestock, Michael B.

, p. 4868 - 4881 (2008/03/12)

Oxazolidinones represent a new and promising class of antibacterial agents. Current research in this area is mainly concentrated on improving the safety profile and the antibacterial spectrum. Oxazolidinones bearing a (pyridin-3-yl)phenyl moiety (e.g., 3) generally show improved antibacterial activity compared to linezolid but suffer from potent monoamine oxidase A (MAO-A) inhibition and low solubility. We now disclose the finding that new analogues of 3 with acyclic substituents on the pyridyl moiety exhibit excellent activity against Gram-positive pathogens, including linezolid-resistant Streptococcus pneumoniae. Generally, more bulky substituents yielded significantly reduced MAO-A inhibition relative to the unsubstituted compound 3. The MAO-A SAR can be rationalized on the basis of docking studies using a MAO-A/MAO-B homology model. Solubility was enhanced with incorporation of polar groups. One optimized analogue, compound 13, showed low clearance in the rat and efficacy against S. pneumoniae in a mouse pneumonia model.

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