165115-89-9

Usage

Uses

Used in Pharmaceutical Research:
[3S-[3alpha(S),5alpha]]-3-[[5-(2,4-Difluorophenyl)tetrahydro-5-(iodomethyl)-3-furanyl]carbonyl]-4-(phenylmethyl)-2-oxazolidinone is used as a candidate molecule for the development of new drugs in the pharmaceutical industry. Its unique structure and functional groups make it a promising starting point for the design of therapeutic agents targeting various medical conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, [3S-[3alpha(S),5alpha]]-3-[[5-(2,4-Difluorophenyl)tetrahydro-5-(iodomethyl)-3-furanyl]carbonyl]-4-(phenylmethyl)-2-oxazolidinone can be utilized as a key intermediate or building block in the synthesis of more complex molecules. Its specific stereochemistry and functional groups may facilitate the creation of novel compounds with tailored properties for various applications.
Used in Material Science:
[3S-[3alpha(S),5alpha]]-3-[[5-(2,4-Difluorophenyl)tetrahydro-5-(iodomethyl)-3-furanyl]carbonyl]-4-(phenylmethyl)-2-oxazolidinone [3S-[3alpha(S),5alpha]]-3-[[5-(2,4-Difluorophenyl)tetrahydro-5-(iodomethyl)-3-furanyl]carbonyl]-4-(phenylmethyl)-2-oxazolidinone may also find applications in material science, where its unique structural features could be exploited to develop new materials with specific properties, such as improved stability, reactivity, or selectivity in various chemical processes.
Used in Analytical Chemistry:
In analytical chemistry, [3S-[3alpha(S*),5alpha]]-3-[[5-(2,4-Difluorophenyl)tetrahydro-5-(iodomethyl)-3-furanyl]carbonyl]-4-(phenylmethyl)-2-oxazolidinone could serve as a reference material or standard for the development and validation of new analytical methods, particularly those involving the analysis of complex organic molecules. Its distinct structure and stereochemistry make it a suitable candidate for such applications.

Upstream product

• 110931-77-6 4-(2,4-difluorophenyl)-4-oxobutanoic acid 
• 165115-74-2 (R)-4-benzyl-3-(4-(2,4-difluorophenyl)pent-4-enoyl)oxazolidin-2-one 
• 182009-45-6 (R)-4-benzyl-3-((S)-4-(2,4-difluorophenyl)-2-(hydroxymethyl)pent-4-enoyl)oxazolidin-2-one 
• 372-18-9 1,3-Difluorobenzene 

Downstream Products

• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 182210-71-5 ((3R,5R)-5-(2,4-difluorophenyl)-5-(iodomethyl)tetrahydrofuran-3-yl)methanol 
• 160709-02-4 ((3R,5R)-5-((1H-1,2,4-triazole-1-yl) methyl)-5-(2,4-difluorophenyl) tetrahydrofuran-3-yl)methanol 
• 149809-43-8 (2R-cis)-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran 

Relevant academic research and scientific papers

Development of posaconazole-based analogues as hedgehog signaling pathway inhibitors

Inhibition of the hedgehog (Hh) signaling pathway has been validated as a therapeutic strategy to treat basal cell carcinoma and holds potential for several other forms of human cancer. Itraconazole and posaconazole are clinically useful triazole anti-fungals that are being repurposed as anti-cancer agents based on their ability to inhibit the Hh pathway. We have previously demonstrated that removal of the triazole from itraconazole does not affect its ability to inhibit the Hh pathway while abolishing its primary side effect, potent inhibition of Cyp3A4. To develop structure-activity relationships for the related posaconazole scaffold, we synthesized and evaluated a series of des-triazole analogues designed through both ligand- and structure-based methods. These compounds demonstrated improved anti-Hh properties compared to posaconazole and enhanced stability without inhibiting Cyp3A4. In addition, we utilized a series of molecular dynamics and binding energy studies to probe specific interactions between the compounds and their proposed binding site on Smoothened. These studies strongly suggest that the tetrahydrofuran region of the scaffold projects out of the binding site and that π-π interactions between the compound and Smoothened play a key role in stabilizing the bound analogues.

AZOLE ANALOGUES AND METHODS OF USE THEREOF

Disclosed herein are analogues of itraconazole that are both angiogenesis and hedgehog signaling pathway inhibitors, formulations thereof, including lipsome formulations thereof. The compounds are expected to be useful in the treatment of cell proliferation disorders such as cancer, particularly cancers that are dependent upon the hedgehog signaling pathway such as basal cell carcinoma and medulloblastoma.

PROCESS FOR PREPARING POSACONAZOLE AND INTERMEDIATES THEREOF

The present invention relates to an industrially advantageous process for the preparation of tetrahydrofuran antifungals preferably posaconazole of formula I. The present invention further relates to improved processes for preparing key and novel intermediates useful in the preparation of posaconazole. The present invention further relates to improved processes for preparing the compound of formula II, a key intermediate in the preparation of posaconazole.

Concise asymmetric routes to 2,2,4-trisubstituted tetrahydrofurans via chiral titanium imide enolates: Key intermediates towards synthesis of highly active azole antifungals Sch 51048 and Sch 56592

Two complimentary approaches to the key (-)-(2R)-cis-tosylate 1 and its (+)-(2S)-enantiomer 15 via generation of chiral imide enolates having a 2,2-disubstituted olefin functionality in the β-position, are described. In a 'protecting group free' sequence, reaction of the titanium enolate generated from (4R)-benzyl-2-oxazolidinone derived imide 5b with s-trioxane provided a convenient intermediate 19 which could be directly subjected to 2,4-diastereoselective iodocyclization.