Identification of an indole series of prostaglandin D2 receptor antagonists
A novel indole series of PGD2 receptor (DP receptor) antagonists is presented. Optimization of this series led to the identification of potent and selective DP receptor antagonists. In particular, antagonists 35 and 36 were identified with Ki values of 2.6 and 1.8 nM, respectively. These two antagon...
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| Published in: | Bioorganic & medicinal chemistry letters Vol. 16; no. 11; pp. 3043 - 3048 |
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| Main Authors: | , , , , , , , , , , , , , , , , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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01-06-2006
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| Abstract | A novel indole series of PGD2 receptor (DP receptor) antagonists is presented. Optimization of this series led to the identification of potent and selective DP receptor antagonists. In particular, antagonists 35 and 36 were identified with Ki values of 2.6 and 1.8 nM, respectively. These two antagonists are also potent in a DP functional assay where they inhibit the PGD2 induced cAMP production in platelet rich plasma with IC50 values of 7.9 and 8.6 nM, respectively. The structure-activity relationships of this indole series of DP receptor antagonists will also be discussed. |
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| AbstractList | A novel indole series of PGD2 receptor (DP receptor) antagonists is presented. Optimization of this series led to the identification of potent and selective DP receptor antagonists. In particular, antagonists 35 and 36 were identified with Ki values of 2.6 and 1.8 nM, respectively. These two antagonists are also potent in a DP functional assay where they inhibit the PGD2 induced cAMP production in platelet rich plasma with IC50 values of 7.9 and 8.6 nM, respectively. The structure-activity relationships of this indole series of DP receptor antagonists will also be discussed. |
| Author | SAWYER, Nicole LIANHAI LI STURINO, Claudio F METTERS, Kathleen M ROY, Bruno BERTHELETTE, Carl O'NEILL, Gary LACHANCE, Nicolas CARRIERE, Marie-Claude DENIS, Danielle SLIPETZ, Deborah BOYD, Michael BRIDEAU, Christine GREIG, Gillian LABELLE, Marc KARGMAN, Stacia MATHIEU, Marie-Claude YOUNG, Robert N LAMONTAGNE, Sonia ZAMBONI, Robert CAUCHON, Elizabeth TSOU, Nancy ZHAOYIN WANG SCHEIGETZ, John |
| Author_xml | – sequence: 1 givenname: Claudio F surname: STURINO fullname: STURINO, Claudio F organization: Department of Medicinal Chemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 2 givenname: Nicolas surname: LACHANCE fullname: LACHANCE, Nicolas organization: Department of Medicinal Chemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 3 givenname: Elizabeth surname: CAUCHON fullname: CAUCHON, Elizabeth organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 4 givenname: Marie-Claude surname: CARRIERE fullname: CARRIERE, Marie-Claude organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 5 givenname: Danielle surname: DENIS fullname: DENIS, Danielle organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 6 givenname: Gillian surname: GREIG fullname: GREIG, Gillian organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 7 givenname: Stacia surname: KARGMAN fullname: KARGMAN, Stacia organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 8 givenname: Sonia surname: LAMONTAGNE fullname: LAMONTAGNE, Sonia organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 9 givenname: Marie-Claude surname: MATHIEU fullname: MATHIEU, Marie-Claude organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 10 givenname: Nicole surname: SAWYER fullname: SAWYER, Nicole organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 11 givenname: Deborah surname: SLIPETZ fullname: SLIPETZ, Deborah organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 12 givenname: Gary surname: O'NEILL fullname: O'NEILL, Gary organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 13 givenname: Michael surname: BOYD fullname: BOYD, Michael organization: Department of Medicinal Chemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 14 surname: ZHAOYIN WANG fullname: ZHAOYIN WANG organization: Department of Medicinal Chemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 15 givenname: Robert surname: ZAMBONI fullname: ZAMBONI, Robert organization: Department of Medicinal Chemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 16 givenname: Kathleen M surname: METTERS fullname: METTERS, Kathleen M organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 17 givenname: Robert N surname: YOUNG fullname: YOUNG, Robert N organization: Department of Medicinal Chemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 18 givenname: Carl surname: BERTHELETTE fullname: BERTHELETTE, Carl organization: Department of Medicinal Chemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 19 givenname: Marc surname: LABELLE fullname: LABELLE, Marc organization: Department of Medicinal Chemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 20 surname: LIANHAI LI fullname: LIANHAI LI organization: Department of Medicinal Chemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 21 givenname: Bruno surname: ROY fullname: ROY, Bruno organization: Department of Medicinal Chemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 22 givenname: John surname: SCHEIGETZ fullname: SCHEIGETZ, John organization: Department of Medicinal Chemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada – sequence: 23 givenname: Nancy surname: TSOU fullname: TSOU, Nancy organization: Department of Medicinal Chemistry, Merck Research Laboratories, PO Box 2000, Rahway, NJ 07065, United States – sequence: 24 givenname: Christine surname: BRIDEAU fullname: BRIDEAU, Christine organization: Department of Biochemistry, Merck Frosst Canada & Co., 16711 Trans Canada Hwy, Kirkland, Que., H9H 3L1, Canada |
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| Keywords | PGD2 Purine nucleotide DP receptor antagonist Arachidonic acid derivatives Prostaglandin G2 DP prostanoid receptor Indole Cyclic AMP Polyunsaturated fatty acid Selectivity Prostaglandin D2 In vitro Optimization Blood plasma Platelet Structure activity relation Production Antagonist Inhibition Indole derivatives Chemical synthesis |
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| SubjectTerms | Biological and medical sciences Histamine and antagonists. Allergy Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Medical sciences Molecular Structure Pharmacology. Drug treatments Receptors, Immunologic - antagonists & inhibitors Receptors, Immunologic - metabolism Receptors, Prostaglandin - antagonists & inhibitors Receptors, Prostaglandin - metabolism Safrole - analogs & derivatives Safrole - chemistry Structure-Activity Relationship |
| Title | Identification of an indole series of prostaglandin D2 receptor antagonists |
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