130209-77-7

Basic information

• Product Name: 15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester
• Synonyms: 15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester
• CAS NO: 130209-77-7
• Molecular Formula: C₂₆H₃₆O₅
• Molecular Weight: 428.56104
• Mol File: 130209-77-7.mol

Chemical Properties

• Boiling Point: 569.8°Cat760mmHg
• Flash Point: 184.4°C
• Appearance: /
• Density: 1.138g/cm³
• Vapor Pressure: 8.04E-14mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: 15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester(130209-77-7)
• EPA Substance Registry System: 15-keto-17-phenyl-18,19,20-trinorprostaglandin F2 alpha-1-isopropyl ester(130209-77-7)

Safety Data

• Hazardous Substances Data: 130209-77-7(Hazardous Substances Data)

Usage

Synthetic chemical compound

Derived from the natural prostaglandin F2 alpha.

Common use

Research and pharmaceutical applications.

Agonist

Potent and selective agonist of the prostaglandin F receptor.

Therapeutic potential

Studied for conditions such as glaucoma, asthma, and labor induction.

1-isopropyl ester structure

Provides enhanced stability and improved pharmacokinetic properties.

Valuable tool

For studying the biological functions and signaling pathways of prostaglandin receptors.

Phenyl substitution

At the 17th carbon position, which may confer specific binding interactions and modulate the compound's pharmacological activity.

InChI:InChI=1/C26H36O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,16-17,19,22-25,28-29H,4,9,12-15,18H2,1-2H3/b8-3-,17-16+/t22-,23-,24+,25-/m1/s1

Upstream product

• 130209-76-6 15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 
• 41162-19-0 dimethyl(2-oxo-4-phenylbutyl)phosphonate 
• 177616-22-7 (Z)-7-((1R,2S,3R,5S)-3,5-Dihydroxy-2-hydroxymethyl-cyclopentyl)-hept-5-enoic acid isopropyl ester 
• 38344-08-0 (5Z)-bimatoprost acid 

Downstream Products

• 130273-87-9 15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 
• 130209-76-6 15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester 
• 177768-49-9 (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2R,3R)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester 
• 177768-48-8 (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester 

Relevant articles and documents

Regio- and stereoselective reactions of 17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Novel prostaglandin F2α derivatives, functionalized at C13 and C14, have been prepared. 17-Phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester [(15S)-1] and its epimer [(15A)-1] were stereoselectively epoxidized, using Sharpless conditions, to produce each of the four diastereomeric epoxides (15S)-2, (15S)-3, (15R)-2, and (15R)-3. Treatment of the four epoxides with LiOH stereospecifically-produced the pentahydroxy substituted analogues 12 and 13. Alternatively, epoxides 2 and 3 were allowed to react with thiophenolate ion. The attack of the sulfur nucleophile on the epoxide occurred at either C13 or C14 depending on the stereochemistry of the epoxide and of C15.

Phenyl-Substituted Prostaglandins: Potent and Selective Antiglaucoma Agents

A series of phenyl-substituted analoques of prostaglandin F2α (PGF2α) were prepared and evaluated for ocular hypotensive effect and side effects in different animal models.In addition, the activity of the analogues on FP receptors was studied in vitro.The results were compared with those of PGF2α and its isopropyl ester.The phenyl-substituted PGF2α analogues exhibited good intraocular pressure reducing effect, were more selective, and exhibited a much higher therapeutic index in the eye than PGF2α or its isopropyl ester.The analogues exhibited high activity on FP receptors in a stereoselective manner for the 15a-hydroxyl group.