| A Novel Convergent Synthesis of the Antiglaucoma PGF(2α) Analogue Bimatoprost. | |
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MedLine Citation:
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PMID: 23381781 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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The 17-phenyl PGF(2α) analogue bimatoprost (10a) is the most efficacious ocular hypotensive agent currently available for the treatment of glaucoma or ocular hypertension. A novel convergent synthesis of 13,14-en-15-ol prostamideF(2α) analogues was developed employing Julia-Lythgoe olefination of the structurally advanced phenylsulfone (+)-(5Z)-15 with an enantiomerically pure aldehyde ω-chain synthon (-)-(S)-16a. Subsequent hydrolysis of protecting groups and final amidation of the diol 26a yielded bimatoprost (10a). The main advantage of the current strategy is the preparation of high-purity bimatoprost (10a). The novel convergent strategy allows the synthesis of a whole series of 13,14-en-15-ol prostamideF(2α) analogues with the desired C-15 asymmetric center configuration from a common and structurally advanced prostaglandin intermediate (+)-(5Z)-15. The preparation and identification of two synthetic impurities, 15-epi isomer (10b) of bimatoprost and a new prostaglandin related amide (+)-(5Z)-18, are also described. Chirality, 2013. © 2013 Wiley Periodicals, Inc. |
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Authors:
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Iwona Dams; Michał Chodyński; Małgorzata Krupa; Anita Pietraszek; Marta Zezula; Piotr Cmoch; Monika Kosińska; Andrzej Kutner |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2013-2-5 |
Journal Detail:
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Title: Chirality Volume: - ISSN: 1520-636X ISO Abbreviation: Chirality Publication Date: 2013 Feb |
Date Detail:
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Created Date: 2013-2-5 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 8914261 Medline TA: Chirality Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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Copyright © 2013 Wiley Periodicals, Inc. |
Affiliation:
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R&D Chemistry Department, Pharmaceutical Research Institute, Rydygiera 8, 01-793, Warsaw, Poland. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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