A Novel Convergent Synthesis of the Antiglaucoma PGF2α Analogue Bimatoprost
ABSTRACT The 17‐phenyl PGF2α 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 prostamideF2α analogues was developed employing Julia–Lythgoe olefination...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2013-03, Vol.25 (3), p.170-179 |
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| container_title | Chirality (New York, N.Y.) |
| container_volume | 25 |
| creator | Dams, Iwona Chodyński, Michał Krupa, Małgorzata Pietraszek, Anita Zezula, Marta Cmoch, Piotr Kosińska, Monika Kutner, Andrzej |
| description | ABSTRACT
The 17‐phenyl PGF2α 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 prostamideF2α 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 prostamideF2α 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 25:170–179, 2013. © 2013 Wiley Periodicals, Inc. |
| doi_str_mv | 10.1002/chir.22123 |
| format | Article |
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The 17‐phenyl PGF2α 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 prostamideF2α 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 prostamideF2α 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 25:170–179, 2013. © 2013 Wiley Periodicals, Inc.</description><identifier>ISSN: 0899-0042</identifier><identifier>EISSN: 1520-636X</identifier><identifier>DOI: 10.1002/chir.22123</identifier><identifier>PMID: 23381781</identifier><language>eng</language><publisher>United States: Blackwell Publishing Ltd</publisher><subject>Amides - chemical synthesis ; Amides - chemistry ; Bimatoprost ; Cloprostenol - analogs & derivatives ; Cloprostenol - chemical synthesis ; Cloprostenol - chemistry ; Corey lactone ; Dinoprost - analogs & derivatives ; Dinoprost - chemical synthesis ; Glaucoma - drug therapy ; Molecular Structure ; nucleophilic addition ; prostaglandins ; prostamides</subject><ispartof>Chirality (New York, N.Y.), 2013-03, Vol.25 (3), p.170-179</ispartof><rights>Copyright © 2013 Wiley Periodicals, Inc</rights><rights>Copyright © 2013 Wiley Periodicals, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchir.22123$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchir.22123$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27922,27923,45572,45573</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23381781$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dams, Iwona</creatorcontrib><creatorcontrib>Chodyński, Michał</creatorcontrib><creatorcontrib>Krupa, Małgorzata</creatorcontrib><creatorcontrib>Pietraszek, Anita</creatorcontrib><creatorcontrib>Zezula, Marta</creatorcontrib><creatorcontrib>Cmoch, Piotr</creatorcontrib><creatorcontrib>Kosińska, Monika</creatorcontrib><creatorcontrib>Kutner, Andrzej</creatorcontrib><title>A Novel Convergent Synthesis of the Antiglaucoma PGF2α Analogue Bimatoprost</title><title>Chirality (New York, N.Y.)</title><addtitle>Chirality</addtitle><description>ABSTRACT
The 17‐phenyl PGF2α 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 prostamideF2α 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 prostamideF2α 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. 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The 17‐phenyl PGF2α 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 prostamideF2α 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 prostamideF2α 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 25:170–179, 2013. © 2013 Wiley Periodicals, Inc.</abstract><cop>United States</cop><pub>Blackwell Publishing Ltd</pub><pmid>23381781</pmid><doi>10.1002/chir.22123</doi><tpages>10</tpages></addata></record> |
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| source | Wiley-Blackwell Journals; MEDLINE |
| subjects | Amides - chemical synthesis Amides - chemistry Bimatoprost Cloprostenol - analogs & derivatives Cloprostenol - chemical synthesis Cloprostenol - chemistry Corey lactone Dinoprost - analogs & derivatives Dinoprost - chemical synthesis Glaucoma - drug therapy Molecular Structure nucleophilic addition prostaglandins prostamides |
| title | A Novel Convergent Synthesis of the Antiglaucoma PGF2α Analogue Bimatoprost |
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