Discovery of 1,3-disubstituted-1H-pyrrole derivatives as potent Melanin-Concentrating Hormone Receptor 1 (MCH-R1) antagonists
The optimization of an HTS-derived hit compound into a potent and metabolically stable MCH-R1 antagonist is described. A series of 1,3-disubstituted-1H-pyrrole-based antagonists of the human Melanin-Concentrating Hormone Receptor 1 (h-MCH-R1) are reported. High-throughput screening of the AstraZenec...
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| Published in | Bioorganic & medicinal chemistry Vol. 18; no. 17; pp. 4859 - 4863 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Oxford
Elsevier Ltd
01.09.2008
Elsevier |
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| Abstract | The optimization of an HTS-derived hit compound into a potent and metabolically stable MCH-R1 antagonist is described.
A series of 1,3-disubstituted-1H-pyrrole-based antagonists of the human Melanin-Concentrating Hormone Receptor 1 (h-MCH-R1) are reported. High-throughput screening of the AstraZeneca compound collection yielded 1, a hit with moderate affinity towards MCH-R1. Subsequent structural manipulations and SAR analysis served to rationalize potency requirements, and 12 was identified as a novel, functional MCH-R1 antagonist with favorable pharmacokinetic properties. |
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| AbstractList | A series of 1,3-disubstituted-1H-pyrrole-based antagonists of the human Melanin-Concentrating Hormone Receptor 1 (h-MCH-R1) are reported. High-throughput screening of the AstraZeneca compound collection yielded 1, a hit with moderate affinity towards MCH-R1. Subsequent structural manipulations and SAR analysis served to rationalize potency requirements, and 12 was identified as a novel, functional MCH-R1 antagonist with favorable pharmacokinetic properties. The optimization of an HTS-derived hit compound into a potent and metabolically stable MCH-R1 antagonist is described. A series of 1,3-disubstituted-1H-pyrrole-based antagonists of the human Melanin-Concentrating Hormone Receptor 1 (h-MCH-R1) are reported. High-throughput screening of the AstraZeneca compound collection yielded 1, a hit with moderate affinity towards MCH-R1. Subsequent structural manipulations and SAR analysis served to rationalize potency requirements, and 12 was identified as a novel, functional MCH-R1 antagonist with favorable pharmacokinetic properties. |
| Author | Gradén, Henrik Morgan, David G.A. Egner, Bryan J. Berglund, Susanne Gradén, Joakim Inghardt, Tord Giordanetto, Fabrizio |
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| Cites_doi | 10.1021/jm070759m 10.1038/25341 10.1517/17460441.2.10.1301 10.1152/ajpendo.00350.2002 10.1038/nrd2037 10.2165/00063030-200721050-00003 10.1172/JCI10660 10.2174/092986708784049621 10.1016/S0014-2999(02)01314-6 10.1021/jm0490890 |
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| Keywords | MCH-R1 antagonists Obesity MCH Melanin-Concentrating Hormone Intravenous administration Rodentia Oral administration In vitro Melanin-Concentrating Hormone;MCH;MCH-R1 antagonists;Obesity Pyrrole derivatives In vivo Vertebrata Mammalia Structure activity relation Mouse Animal Chlorine Organic compounds Piperidine derivatives Melanin concentrating hormone Carboxamide Antagonist Fluorine Organic compounds Pharmacokinetics Chemical synthesis Nutritional status Biological receptor Hormonal receptor |
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| References | Souers, Gao, Brune, Bush, Wodka, Vasudevan, Judd, Mulhern, Brodjian, Dayton, Shapiro, Hernandez, Marsh, Sham, Collins, Kym (bib8) 2005; 48 Ludwig, Tritos, Mastaitis, Kulkarni, Kokkotou, Elmiqst, Lowell, Flier, Maratos-Flier (bib3) 2001; 107 Cavasotto, Orry, Murgolo, Czarniecki, Kocsi, Hawes, O’Neill, Hine, Burton, Voigt, Abagyan, Bayne, Monsma (bib11) 2008; 51 Shimada, Tritos, Lowell, Flier, Maratos-Flier (bib4) 1998; 396 and in: (b) Egner, B. J.; Giordanetto, F.; Inghardt, T. WO2006/0685594 (Compounds Takekawa, Asami, Ishihara, Terauchi, Kato, Shimomura, Mori, Murakoshi, Kato, Suzuki, Nishimura, Fujino (bib9) 2002; 438 Rivera, Bocanegra-Garcia, Galiano, Cirauqui, Ceras, Perez, Aldana, Monge (bib5) 2008; 15 , . Kowalski, Sasikumar (bib6) 2007; 21 – Giordanetto, F.; Lindberg, J.; Karlsson, O.; Inghardt, T. Abstract of Papers, 232nd National Meeting of the American Chemical Society, San Francisco, CA, 2006, Abstract 0410. Melnikova, Wages (bib1) 2006; 5 Rokosz (bib7) 2007; 2 The preparation of key compounds is described in: (a) Brickmann, K.; Egner, B. J.; Giordanetto F.; Inghardt, T.; Linusson, A.; Ponten, F. WO2005/090330 (Compounds Gomori, Ishiara, Ito, Mashiko, Matsuhita, Yumoto, Ito, Tanaka, Tokita, Moriya, Iwaasa, Kanatani (bib2) 2003; 284 10.1016/j.bmcl.2008.07.079_bib12 Ludwig (10.1016/j.bmcl.2008.07.079_bib3) 2001; 107 10.1016/j.bmcl.2008.07.079_bib10 Rokosz (10.1016/j.bmcl.2008.07.079_bib7) 2007; 2 Takekawa (10.1016/j.bmcl.2008.07.079_bib9) 2002; 438 Souers (10.1016/j.bmcl.2008.07.079_bib8) 2005; 48 Gomori (10.1016/j.bmcl.2008.07.079_bib2) 2003; 284 Melnikova (10.1016/j.bmcl.2008.07.079_bib1) 2006; 5 Kowalski (10.1016/j.bmcl.2008.07.079_bib6) 2007; 21 Cavasotto (10.1016/j.bmcl.2008.07.079_bib11) 2008; 51 Shimada (10.1016/j.bmcl.2008.07.079_bib4) 1998; 396 Rivera (10.1016/j.bmcl.2008.07.079_bib5) 2008; 15 |
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| Snippet | The optimization of an HTS-derived hit compound into a potent and metabolically stable MCH-R1 antagonist is described.
A series of... A series of 1,3-disubstituted-1H-pyrrole-based antagonists of the human Melanin-Concentrating Hormone Receptor 1 (h-MCH-R1) are reported. High-throughput... A series of 1,3-disubstituted-1H-pyrrole-based antagonists of the human Melanin-Concentrating Hormone Receptor 1 (h-MCH-R1) are reported. High- throughput... |
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| SubjectTerms | Animals Anti-Obesity Agents - chemistry Anti-Obesity Agents - pharmacokinetics Anti-Obesity Agents - pharmacology Biological and medical sciences Drug Stability Hormones. Endocrine system Humans MCH MCH-R1 antagonists Medical sciences Melanin-Concentrating Hormone Mice Obesity Pharmacology. Drug treatments Pyrroles - chemistry Pyrroles - pharmacokinetics Pyrroles - pharmacology Receptors, Somatostatin - antagonists & inhibitors Receptors, Somatostatin - metabolism Structure-Activity Relationship |
| Title | Discovery of 1,3-disubstituted-1H-pyrrole derivatives as potent Melanin-Concentrating Hormone Receptor 1 (MCH-R1) antagonists |
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