17-phenyl-trinor-PGF2alpha isopropyl ester

Base Information

• Chemical Name: 17-phenyl-trinor-PGF2alpha isopropyl ester
• CAS No.: 130209-76-6
• Molecular Formula: C26H38 O5
• Molecular Weight: 430.585
• European Community (EC) Number: 691-872-7
• UNII: 1IFH52MD8T
• Nikkaji Number: J528.514C
• Wikidata: Q27252458
• Metabolomics Workbench ID: 2470
• ChEMBL ID: CHEMBL2111623
• Mol file: 130209-76-6.mol

Synonyms:17-phenyl-18,19,20-trinor-PGF2alpha-1-isopropyl ester;17-phenyl-18,19,20-trinor-prostaglandin F2 alpha-1-isopropyl ester;PhDH100A

Chemical Property of 17-phenyl-trinor-PGF2alpha isopropyl ester

Chemical Property:

• Vapor Pressure: 5.47E-14mmHg at 25°C
• Boiling Point: 573.4°Cat760mmHg
• PKA: 14.25±0.20(Predicted)
• Flash Point: 185°C
• PSA: 86.99000
• Density: 1.141g/cm³
• LogP: 3.96240
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 430.27192431
• Heavy Atom Count: 31
• Complexity: 564

Purity/Quality:

98% min ^*data from raw suppliers

17-phenyl trinor Prostaglandin F2α isopropyl ester ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O
• Isomeric SMILES: CC(C)OC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](CCC2=CC=CC=C2)O)O)O
• Description: 17-phenyl trinor PGF2α N-ethyl amide is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug, sold under the Allergan trade name Bimatoprost. The N-ethyl amide prostaglandin prodrugs are converted to the active free acid more slowly than the analogous prostaglandin ester prodrugs such as latanoprost. This product is the isopropyl ester of the free acid prostaglandin which corresponds to Bimatoprost. The free acid, 17-phenyl trinor PGF2α, is a potent FP receptor agonist. In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity. The 17-phenyl trinor PGF2α isopropyl ester derivative was examined for IOP-lowering activity during the development of latanoprost. At the dose of 3 μg/eye in the monkey, 17-phenyl trinor PGF2α isopropyl ester was the most potent analog tested in reducing IOP, lowering the IOP 1.3 mm Hg below the level achieved by latanoprost. However, this derivative was also significantly more irritating to the eye than latanoprost.

Technology Process of 17-phenyl-trinor-PGF2alpha isopropyl ester

There total 7 articles about 17-phenyl-trinor-PGF2alpha isopropyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

2-iodo-propane (75-30-9) + (5Z)-bimatoprost acid (38344-08-0) → 15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130209-76-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; for 10h; Ambient temperature;

DOI:10.1021/jm00054a008

Reference yield: 28.0%

15-keto-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130209-77-7) → 15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130273-87-9) + 15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130209-76-6)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; dichloromethane; for 0.5h;

DOI:10.1021/jm00054a008

Reference yield:

Isopropyl (Z)-7-((1R,2R,3R,5S)-2-((3S,E)-3-(tert-butyldimethylsilyloxy)-5-phenyl-pent-1-enyl)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclopentyl)-hept-5-enoate (1190883-22-7) → 15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130209-76-6)

Guidance literature:

With hydrogen fluoride; In water; isopropyl alcohol; Product distribution / selectivity;

upstream raw materials:

2-iodo-propane

(5Z)-bimatoprost acid

15-keto-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester

dimethyl(2-oxo-4-phenylbutyl)phosphonate

Downstream raw materials:

15-keto-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester

(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((S)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester

(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2R,3R)-3-((S)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester

17-phenyl-trinor-prostaglandin F2α isobutylamide

Refernces

• 1、 -. "9,11-cycloendoperoxide pro-drugs of prostaglandin analogues for treatment of ocular hypertension and glaucoma". Page/Page column 14-15. . Retrieved 2010/11/30.
• 2、 Resul, Bahram,Stjernschantz, Johan,No, Kiyo,Liljebris, Charlotta,Selen, Goeran,et al.. "Phenyl-Substituted Prostaglandins: Potent and Selective Antiglaucoma Agents". . p. 243 - 248. Retrieved 2007/10/02.