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Welcome to the BioBlocks Bulletin
The BioBlocks Bulletin brings you recent research on key classes of building blocks. In this issue we introduce new 2- and 4-piperazin-1-yl-quinolines. Application of these building blocks to medicinal chemistry programs is described.
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Application Update
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i) K2CO3, CH3CN, 80 oC, 2h, ii) LiAlH4, THF, reflux, 2h, iii) BBr3, -78 oC, CH2Cl2, overnight
iv) 2-bromoethanol, K2CO3, CH3CN, reflux, v) oxalylchloride, DMSO, Et3N, -78 oC
vi) NaCNBH3, AcOH, 1,2-dichloroethane
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Dutta, Aloke K., et al., J. Med. Chem., 2010, 53, 1023 – 1037
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i) Na(OAc)3BH, AcOH, 1,2-dichloroethane, 23 oC, 12h
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Patent: American Home Products; US 2002045628 (A1)
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Matsuno, Kenji, et al., J. Med. Chem. 2003, 46, 4910 - 4925
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Literature References
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| 1. |
Balaram Ghosh, Tamara Antonio, Juan Zhen, Prashant Kharkar, Maarten E. A. Reith and Aloke K. Dutta
Development of (S)-N6-(2-(4-(Isoquinolin-1-yl)piperazin-1-yl)ethyl)- N6-propyl-4,5,6,7-tetrahydrobenzo[d]-thiazole-2,6-diamine and Its Analogue as a D3 Receptor Preferring Agonist: Potent in Vivo Activity in Parkinson’s Disease Animal Model
Dutta and co-workers from Wayne State University present SAR on a series of D3 receptor agonists out which two compounds are shown to exhibit high in vivo activity in Parkinson’s disease animal models. Included in the series are products derived from BioBlocks QU891 which display comparable Kis to the lead molecules. Alkylation of QU891 with substituted 2-chloro-N-(1,2,3,4-tetrahydro-naphthalen-2-yl)-acetamides followed by reduction of the amide and then BBr3 demethylation afforded the tetrahydro-naphthalene target molecules. Alkylation of QU891 with bromoethanol followed by Swern oxidation led to the corresponding aldehyde which was reductively aminated with S-(-)-Pramipexole to produce the desired aminothiazolidium product.
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| 2. |
Richard E Mewshaw, Ping Zhou, Dahui Zhou, Kristin L Meagher, Magda Asselin, Deborah A Evrard, Adam M Gilbert
Arylpiperazinyl-cyclohexyl indole derivatives for the treatment of depression
Scientists at American Home Products disclose a class of arylpiperazinyl derivatives as 5HT1A antagonists useful for potential treatment of diseases affected by disorders of the serotonin-affected neurological systems, such as depression and anxiety. Within the series is a set of quinolinyl-piperazines derived from BioBlocks QU3083-1 through reductive alkylation with a set of substituted 4-(1H-Indol-3-yl)-cyclohexanones.
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| 3. |
Kenji Matsuno, Junko Ushiki, Takashi Seishi, Michio Ichimura, Neill A. Giese, Jin-Chen Yu, Shusuke Takahashi, Shoji Oda and Yuji Nomoto
Potent and Selective Inhibitors of Platelet-Derived Growth Factor Receptor Phosphorylation. 3. Replacement of Quinazoline Moiety and Improvement of Metabolic Polymorphism of 4-[4-(N- Substituted (thio) carbamoyl)-1-piperazinyl]- 6,7-dimethoxy quinazoline Derivatives
In this third paper of the series on inhibitors of platelet-derived growth factor receptor phosphorylation, Matsuno and co-workers describe the replacement of a quinazolinyl-piperazine moiety with a variety of heterocycles and the resulting inhibitory activities. Within the set of heterocyclic replacements are quinolinyl-piperazines including BioBlocks QU3089-1. Treatment of QU3089-1 with isocyantes and thioisocyanates resulted in the target ureas and thioureas of which sub-micromolar IC50s were observed.
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