Total Synthesis of Prostaglandin 15d-PGJ(2) and Investigation of its Effect on the Secretion of IL-6 and IL-12.

Egger, Julian; Fischer, Stefan; Bretscher, Peter; Freigang, Stefan; Kopf, Manfred; Carreira, Erick M (2015). Total Synthesis of Prostaglandin 15d-PGJ(2) and Investigation of its Effect on the Secretion of IL-6 and IL-12. Organic letters, 17(17), pp. 4340-4343. American Chemical Society 10.1021/acs.orglett.5b02181

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An efficient synthesis of 15-deoxy-Δ12,14-prostaglandin J2 (15d-PGJ2, 1) is reported. The route described allows for diversification of the parent structure to prepare seven analogues of 1 in which the positioning of electrophilic sites is varied. These analogues were tested in SAR studies for their ability to reduce the secretion of proinflammatory cytokines. It was shown that the endocyclic enone is crucial for the bioactivity investigated and that the conjugated ω-side chain serves in a reinforcing manner.

Item Type:

Journal Article (Original Article)

Division/Institute:

04 Faculty of Medicine > Service Sector > Institute of Pathology
04 Faculty of Medicine > Service Sector > Institute of Pathology > Immunopathology

UniBE Contributor:

Freigang, Stefan Bernd

Subjects:

500 Science > 570 Life sciences; biology
600 Technology > 610 Medicine & health

ISSN:

1523-7060

Publisher:

American Chemical Society

Language:

English

Submitter:

Stefan Bernd Freigang

Date Deposited:

30 Mar 2016 11:38

Last Modified:

30 Mar 2016 11:38

Publisher DOI:

10.1021/acs.orglett.5b02181

PubMed ID:

26301727

BORIS DOI:

10.7892/boris.80446

URI:

https://boris.unibe.ch/id/eprint/80446

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