951319-59-8

Basic information

• Product Name: 16-phenoxy Prostaglandin F2α ethyl amide
• Synonyms: 16-phenoxy Prostaglandin F2α ethyl amide;(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]cyclopentyl]-N-ethylhept-5-enamide;16-phenoxy Prostaglandin F2.alpha. ethyl amide
• CAS NO: 951319-59-8
• Molecular Formula: C₂₄H₃₅NO₅
• Molecular Weight: 417.5384
• Mol File: 951319-59-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 16-phenoxy Prostaglandin F2α ethyl amide(CAS DataBase Reference)
• NIST Chemistry Reference: 16-phenoxy Prostaglandin F2α ethyl amide(951319-59-8)
• EPA Substance Registry System: 16-phenoxy Prostaglandin F2α ethyl amide(951319-59-8)

Safety Data

• Hazardous Substances Data: 951319-59-8(Hazardous Substances Data)

Usage

Description

16-phenoxy Prostaglandin F2α ethyl amide is a metabolically stable analog of Prostaglandin F2α (PGF2α), which is a naturally occurring hormone that causes smooth muscle contraction and exhibits potent luteolytic activity. 16-phenoxy Prostaglandin F2α ethyl amide is designed to have a greater affinity for the FP receptor on ovine luteal cells, making it a more effective prodrug for its intended applications.
Used in Pharmaceutical Industry:
16-phenoxy Prostaglandin F2α ethyl amide is used as a prodrug for the treatment of various conditions related to smooth muscle contraction and luteolysis. Its increased affinity for the FP receptor allows for more effective binding and activity, making it a promising candidate for pharmaceutical development.
Used in Veterinary Medicine:
In veterinary medicine, 16-phenoxy Prostaglandin F2α ethyl amide is used as a luteolytic agent to induce the regression of the corpus luteum in animals, which can be beneficial for managing reproductive cycles and treating related conditions.
Used in Research Applications:
16-phenoxy Prostaglandin F2α ethyl amide is also used as a research tool to study the mechanisms of action and signaling pathways related to PGF2α and its receptors. This can help in understanding the role of prostaglandins in various physiological processes and contribute to the development of new therapeutic agents.

Upstream product

• 1201226-16-5 (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide 
• 41639-73-0 (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one 

Relevant articles and documents

A unified strategy to prostaglandins: chemoenzymatic total synthesis of cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost guided by biocatalytic retrosynthesis

Development of efficient and stereoselective synthesis of prostaglandins (PGs) is of utmost importance, owing to their valuable medicinal applications and unique chemical structures. We report here a unified synthesis of PGs cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost from the readily available dichloro-containing bicyclic ketone6aguided by biocatalytic retrosynthesis, in 11-12 steps with 3.8-8.4% overall yields. An unprecedented Baeyer-Villiger monooxygenase (BVMO)-catalyzed stereoselective oxidation of6a(99% ee), and a ketoreductase (KRED)-catalyzed diastereoselective reduction of enones12(87?:?13 to 99?:?1 dr) were utilized in combination for the first time to set the critical stereochemical configurations under mild conditions. Another key transformation was the copper(ii)-catalyzed regioselectivep-phenylbenzoylation of the secondary alcohol of diol10(9.3?:?1 rr). This study not only provides an alternative route to the highly stereoselective synthesis of PGs, but also showcases the usefulness and great potential of biocatalysis in construction of complex molecules.