e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

N-(Methanesulfonyl)-16-phenoxyprostaglandin carboxamides: tissue-selective, uterine stimulants

…, JS Bindra, JF Eggler, JJ Plattner…

Index: Schaaf, Thomas K.; Bindra, Jasjit S.; Eggler, James F.; Plattner, Jacob J.; Nelson, A. James; et al. Journal of Medicinal Chemistry, 1981 , vol. 24, # 11 p. 1353 - 1359

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Citation Number: 31

Abstract

In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sdfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy group were synthesized and evaluated in a variety of in vitro and in vivo models. Several of theae analogues exhibited potent, tissueselective, uterine stimulant activity, a fmding ...

Dimethyl (2-oxo-4-phenylbutyl)phosphonate Structure

Dimethyl (2-oxo...

~%

(+)-(3Ar,4R,5R,6as)-hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one Structure

(+)-(3Ar,4R,5R,...

[1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-5-yl ester Structure

[1,1'-Biphenyl]...

~%

(+)-(3Ar,4R,5R,6as)-hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one Structure

(+)-(3Ar,4R,5R,...

(3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-y l 4-biphenylcarboxylate Structure

(3aR,4R,5R,6aS)...

~%

(+)-(3Ar,4R,5R,6as)-hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one Structure

(+)-(3Ar,4R,5R,...

(Z)-N-(methylsulfonyl)-7-((1R,2R,3R)-5-oxo-2-((3R,E)-4-phenoxy-3-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-1-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enamide Structure

(Z)-N-(methylsu...

~42%

Sulprostone Structure

Methyl 2-phenoxyacetate Structure

Methyl 2-phenox...

lithium anion of dimethyl methylphosphonate Structure

lithium anion o...

~%

Dimethyl 2-oxo-3-phenoxypropylphosphonate Structure

Dimethyl 2-oxo-...

Dimethyl [3-(3-chlorophenoxy)-2-oxopropyl]phosphonate Structure

Dimethyl [3-(3-...

(3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-y l 4-biphenylcarboxylate Structure

(3aR,4R,5R,6aS)...

~%

[1,1'-Biphenyl]-4-carboxylic acid [3aR-[3aa,4a(E),5b,6aa]]-4-[4-(3-chlorophenoxy)-3-oxo-1-butenyl]hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester Structure

[1,1'-Biphenyl]...

Synthesis and in vitro evaluation of human FP-receptor selec...

[DeLong, Mitchell A.; Amburgey, Jack; Taylor, Cynthia; Wos, John A.; Soper, David L.; Wang, Yili; Hicks, Renee Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 14 p. 1519 - 1522]

Synthesis and in vitro evaluation of human FP-receptor selec...

[DeLong, Mitchell A.; Amburgey, Jack; Taylor, Cynthia; Wos, John A.; Soper, David L.; Wang, Yili; Hicks, Renee Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 14 p. 1519 - 1522]

Synthesis and in vitro evaluation of human FP-receptor selec...

[DeLong, Mitchell A.; Amburgey, Jack; Taylor, Cynthia; Wos, John A.; Soper, David L.; Wang, Yili; Hicks, Renee Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 14 p. 1519 - 1522]

Synthesis and in vitro evaluation of human FP-receptor selec...

[DeLong, Mitchell A.; Amburgey, Jack; Taylor, Cynthia; Wos, John A.; Soper, David L.; Wang, Yili; Hicks, Renee Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 14 p. 1519 - 1522]

Synthesis and in vitro evaluation of human FP-receptor selec...

[DeLong, Mitchell A.; Amburgey, Jack; Taylor, Cynthia; Wos, John A.; Soper, David L.; Wang, Yili; Hicks, Renee Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 14 p. 1519 - 1522]