Lead optimization of 4-(dimethylamino)quinazolines, potent and selective antagonists for the melanin-concentrating hormone receptor 1
The synthesis and SAR of 4-(dimethylamino)quinazolines as melanin-concentrating hormone receptor 1 (MCH-R1) antagonists are reported, leading to the discovery of ATC0175. The optimization of a series of 4-(dimethylamino)quinazoline antagonists of the melanin-concentrating hormone receptor 1 (MCH-R1)...
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| Published in: | Bioorganic & medicinal chemistry letters Vol. 15; no. 17; pp. 3853 - 3856 |
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| Main Authors: | , , , , , , , , , , , |
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| Language: | English |
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01-09-2005
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| Abstract | The synthesis and SAR of 4-(dimethylamino)quinazolines as melanin-concentrating hormone receptor 1 (MCH-R1) antagonists are reported, leading to the discovery of ATC0175.
The optimization of a series of 4-(dimethylamino)quinazoline antagonists of the melanin-concentrating hormone receptor 1 (MCH-R1) is described. The combination of the elaboration of both the linker portion and the terminal phenyl ring provided
N-(
cis-4-{[4-(dimethylamino)quinazolin-2-yl]amino}cyclohexyl)-3,4-difluorobenzamide hydrochloride
28 (ATC0175), which showed excellent antagonist activity at the MCH-R1 (IC
50
=
3.4
nM) as well as good selectivity over the Y5 and the α
2A receptors. |
|---|---|
| AbstractList | The synthesis and SAR of 4-(dimethylamino)quinazolines as melanin-concentrating hormone receptor 1 (MCH-R1) antagonists are reported, leading to the discovery of ATC0175.
The optimization of a series of 4-(dimethylamino)quinazoline antagonists of the melanin-concentrating hormone receptor 1 (MCH-R1) is described. The combination of the elaboration of both the linker portion and the terminal phenyl ring provided
N-(
cis-4-{[4-(dimethylamino)quinazolin-2-yl]amino}cyclohexyl)-3,4-difluorobenzamide hydrochloride
28 (ATC0175), which showed excellent antagonist activity at the MCH-R1 (IC
50
=
3.4
nM) as well as good selectivity over the Y5 and the α
2A receptors. The optimization of a series of 4-(dimethylamino)quinazoline antagonists of the melanin-concentrating hormone receptor 1 (MCH-R1) is described. The combination of the elaboration of both the linker portion and the terminal phenyl ring provided N-(cis-4-{[4-(dimethylamino)quinazolin-2-yl]amino}cyclohexyl)-3,4-difluorobenzamide hydrochloride 28 (ATC0175), which showed excellent antagonist activity at the MCH-R1 (IC50 = 3.4 nM) as well as good selectivity over the Y5 and the alpha2A receptors. |
| Author | Funakoshi, Takeo Kanuma, Kosuke Hsu, Debbie Chaki, Shigeyuki Tran, Thuy-Anh Kramer, Bryan Thomsen, Bill Omodera, Katsunori Semple, Graeme Sekiguchi, Yoshinori Casper, Martin Nishiguchi, Mariko |
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| Cites_doi | 10.1124/jpet.104.081711 10.1016/S0014-5793(96)01160-X 10.1038/380243a0 10.1016/S0031-9384(99)00117-1 10.1210/endo-125-3-1660 10.1210/en.138.1.351 10.1038/25341 10.1038/nm0902-1039b 10.1016/j.bmcl.2005.03.052 10.1016/0196-9781(95)02092-6 10.1016/S0014-2999(02)01314-6 |
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| Keywords | Melanin-concentrating hormone receptor 1 antagonists MCH-R1 antagonists ATC0175 Cyclohexane derivatives Spacer arm Quinazoline derivatives Selectivity Optimization Structure activity relation Hydrochlorides Organic fluorine compounds Melanin concentrating hormone Benzamide derivatives Carboxamide Antagonist Chemical synthesis Biological receptor Hormonal receptor |
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| SubjectTerms | ATC0175 Biological and medical sciences Hormones. Endocrine system Humans Inhibitory Concentration 50 MCH-R1 antagonists Medical sciences Melanin-concentrating hormone receptor 1 antagonists Pharmacology. Drug treatments Quinazolines - chemical synthesis Quinazolines - chemistry Quinazolines - pharmacology Radioligand Assay Receptors, Somatostatin - antagonists & inhibitors Structure-Activity Relationship Substrate Specificity |
| Title | Lead optimization of 4-(dimethylamino)quinazolines, potent and selective antagonists for the melanin-concentrating hormone receptor 1 |
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