165115-70-8

Usage

Uses

Used in Organic Synthesis:
4-(2,4-difluorophenyl)-pent-4-enoic acid is used as a building block in organic synthesis for the creation of various complex organic molecules. Its difluorophenyl group and pentenoic acid backbone provide a versatile platform for the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
4-(2,4-difluorophenyl)-pent-4-enoic acid is used as an active pharmaceutical ingredient (API) or as an intermediate in the synthesis of drugs. Its unique structure may offer novel therapeutic properties, making it a promising candidate for the development of new medications.
Used in Materials Science:
4-(2,4-difluorophenyl)-pent-4-enoic acid is used as a component in the development of new materials with specific properties. Its incorporation into polymers, coatings, or composites can lead to materials with improved characteristics, such as enhanced stability, reactivity, or selectivity.

Upstream product

• 110931-77-6 4-(2,4-difluorophenyl)-4-oxobutanoic acid 
• 19493-09-5 Methylenetriphenylphosphorane 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 108-30-5 succinic acid anhydride 
• 372-18-9 1,3-Difluorobenzene 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 141113-36-2 2-(2,4-difluorophenyl)allyl alcohol 

Downstream Products

• 182009-37-6 4-(2,4-Difluoro-phenyl)-pent-4-enoyl chloride 
• 170985-86-1 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-1H-1,2,4-triazol-5(4H)-one 
• 171228-49-2 posaconazote 
• 149809-43-8 (2R-cis)-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran 
• 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 
• 165115-74-2 (R)-4-benzyl-3-(4-(2,4-difluorophenyl)pent-4-enoyl)oxazolidin-2-one 

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.

A PROCESS FOR THE MANUFACTURE OF POSACONAZOLE

The present invention discloses an improved process for the manufacture of Posaconazole, an anti-fungal agent belonging to the category of substituted Tetrahydrofuran Triazole compound. The present invention further describes preparation of formula A and formula B, the key intermediates in the preparation of Posaconazole. The invention also discloses novel intermediates that are useful in the synthesis of Posaconazole.

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.

Preparation method of posaconazole main ring

The invention discloses a preparation method of a posaconazole main ring. The preparation method comprises steps as follows: 1), a compound F is dissolved in an organic solvent I, then thionyl chloride is added for reaction, and a compound G is obtained;

IMPROVED PROCESS FOR THE PREPARATION OF ((3S,5R)-5-((1H-1,2,4-TRIAZOL-1-YL)METHYL)-5-(2,4-DIFLUOROPHENYL)TETRAHYDROFURAN-3-YL)METHYL-4-METHYLBENZENESULFONATE

The present invention relates to process for the preparation of ((3S,5R)-5-((lH-l,2,4- triazol- 1 -yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzene sulfonate compound of formula- 1 through novel intermediates. Further the said compound of formula- 1 is useful as a key intermediate for the preparation of Posaconazole.

Process for the Preparation of Triazole Antifungal Drug, Its Intermediates and Polymorphs Thereof

A process for the preparation of 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-ylmethyl)-3-furanyl]methoxy]phenyl]-1-piperazinyl]phenyl]-2-[(1S,2S)-1-ethyl-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one compound of formula-1, its intermediates and polymorphs thereof. (I)

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.