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

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Author(s): Rama Mohana Reddy Jaggavarapu, Venkatanarayana Muvvala*, Venkata Reddy.G, Ravi Kumar Cheedarala*

Journal Name: Current Organic Synthesis

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Introduction: 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.

Materials and Methods: 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.

Results and Discussions: Moreover, the impurity showing anti-glaucoma properties in docking studies with respect to bimatoprost has been described.

Conclusion: The extention of our work towards docking studies and the present impurity molecule showed almost the same biological activity with respect to Tafluprost.

Keywords: Glaucoma, (Z)-isopropyl 7-((1R, 2R, 3R, 5S)-2-((1E, 3Z)-3-fluoro-4-phenoxybuta-1, 3-dienyl (-3, 5-dihydroxycyclopentyl) hept- 5-enoate, prostaglandins, tafluprost, docking studies.

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(E-pub Ahead of Print)
DOI: 10.2174/1570179417666201209141222
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