Isolation, Characterization, and Docking Studies of (Z)-Isopropyl 7-((1R, 2R, 3R, 5S)- 2-((1E, 3Z)-3-Fluoro-4-Phenoxybuta-1, 3-Dienyl)-3,5-Dihydroxycyclopentyl) Hept-5- Enoate, an Impurity of Tafluprost.

Abstract

The origin, isolation, and characterization of (Z)-isopropyl 7-((1R, 2R, 3R, 5S)-2-((1E, 3Z)-3-fluoro-4-phenoxybuta-1, 3-dienyl)-3, 5-dihydroxycyclopentyl) hept-5-enoate, an impurity found in the preparation of an anti-glaucoma agent-Tafluprost has been described in this study. Further, an enantiospecific synthesis of (Z)-isopropyl 7-((1R, 2R, 3R, 5S)-2-((1E, 3Z)- 3-fluoro-4-phenoxybuta-1, 3-dienyl)-3, 5-dihydroxycyclopentyl) hept-5-enoate has been revealed using deoxofluorination as a key transformation of the strategy. Moreover, the impurity showing anti-glaucoma properties in docking studies with respect to bimatoprost has been described. The extention of our work towards docking studies and the present impurity molecule showed almost the same biological activity with respect to Tafluprost.