Organic Letters

, volume 17 , issue 17 , pages 4340-4343

Total Synthesis of Prostaglandin 15d-PGJ₂ and Investigation of its Effect on the Secretion of IL-6 and IL-12

Julian Egger ¹

S Fischer ¹

Peter A Bretscher ²

Stefan Freigang ²

M Kopf ²

Scott Miller ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Laboratory of Organic Chemistry, ETH Zurich, HCI H335, Wolfgang-Pauli-Strasse 10, 8093 Zurich, Switzerland |

Institute for Integrative Biology, ETH Zurich, HPL-G 12, Schafmattstrasse 27, 8093 Zurich, Switzerland |

Publication type: Journal Article

Publication date: 2015-08-24

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.5b02181

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PubMed ID: 26301727

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

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.

Found

2 citations

Almukhametov Aidar

🥼 🤝

PhD in Chemistry

14 publications, 51 citations

h-index: 4

Sirius University of Science and Technology

Research interests

Chemistry of natural compounds

Medicinal Chemistry

Organic Chemistry

Total synthesis

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Egger J. et al. Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12 // Organic Letters. 2015. Vol. 17. No. 17. pp. 4340-4343.

GOST all authors (up to 50) Copy

Egger J., Fischer S., Bretscher P. A., Freigang S., Kopf M., Miller S. Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12 // Organic Letters. 2015. Vol. 17. No. 17. pp. 4340-4343.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.5b02181

UR - https://doi.org/10.1021/acs.orglett.5b02181

TI - Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12

T2 - Organic Letters

AU - Egger, Julian

AU - Fischer, S

AU - Bretscher, Peter A

AU - Freigang, Stefan

AU - Kopf, M

AU - Miller, Scott

PY - 2015

DA - 2015/08/24

PB - American Chemical Society (ACS)

SP - 4340-4343

IS - 17

VL - 17

PMID - 26301727

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2015_Egger,

author = {Julian Egger and S Fischer and Peter A Bretscher and Stefan Freigang and M Kopf and Scott Miller},

title = {Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12},

journal = {Organic Letters},

year = {2015},

volume = {17},

publisher = {American Chemical Society (ACS)},

month = {aug},

url = {https://doi.org/10.1021/acs.orglett.5b02181},

number = {17},

pages = {4340--4343},

doi = {10.1021/acs.orglett.5b02181}

}

MLA

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MLA Copy

Egger, Julian, et al. “Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12.” Organic Letters, vol. 17, no. 17, Aug. 2015, pp. 4340-4343. https://doi.org/10.1021/acs.orglett.5b02181.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)