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BioBlocks Bulletin
Vol. 9 July 2009 |
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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 describe recent SAR studies with products derived from 4-chloro and 4-aminoquinolines. Members of this family have been used as RET kinase inhibitors and as heme metabolism inhibitors. If you are interested in a related compound, please contact us for inclusion in the growing set of analogs.
In this issue we present 4-chloro, 4-aminoquinolines
The schemes below describe two applications of this versatile product class. At BioBlocks, we believe that providing SAR options is an important goal and have initiated a program to generate a range of these versatile compounds in research quantities. Of particular interest are the building blocks that contain an additional site for functionalization, like the bromo-chloroquinolines used in the second reference.
Our catalog currently contains more then 90 items from this class. Shown below is a sample of the available starting materials, highlighting the range of substitutions available for SAR in your project.
Please scroll down to the bottom of the newsletter to view the references. To order products, shop at
www.bioblocks.com, call (+1) 858 558-5900 or email
sales@bioblocks.com.
BioBlocks is your chemistry partner in drug discovery
Our results-based lead optimization services focus on your project goals. Learn how we can be a cost efficient, innovative resource for your medicinal chemistry needs. |
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QU222
4-Chloro-2-propyl-6-quinolinecarbonitrile
Price: 2.5g = $275.00 |
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QU225
6-Bromo-4-chloro-2-ethylquinoline
Price: 1g = $375.00 |
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QU228
6-Bromo-4-chloro-2-phenylquinoline
Price: 1g = $275.00 |
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4-chloro-2-trichloroquinolines |
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QU028
4-Chloro-6-fluoro-2-trichloromethyl-quinoline
2.5g = $275.00 |
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QU034
4,6-Dichloro-2-trichloromethyl-quinoline
Price: 2.5g = $250.00 |
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QU009
4-Chloro-6-methyl-2-trichloromethyl-quinoline
2.5g = $250.00 |
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QU866
4-Chloro-2-trichloromethyl-6-trifluoromethylquinoline
Price: 1g = $305.00 |
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2-Unsubstituted 4-chloroquinolines |
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QU545
4-Chloro-6-fluoroquinoline
Price: 2.5g = $225.00 |
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QU465
4,6-Dichloroquinoline
Price: 2.5g = $275.00 |
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QU801
6-Bromo-4-chloroquinoline
Price: 2.5g = $360.00 |
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QU800
4-Chloro-6-methylquinoline
Price: 2.5g = $315.00 |
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QU064
4-Chloro-6-methoxyquinoline
Price: 2.5g = $250.00 |
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QU1036
4-Chloro-6-trifluoromethylquinoline
Price: 10g = $280.00 |
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QU548
4-Chloro-7-fluoroquinoline
Price: 1g = $220.00 |
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QU1055
7-Bromo-4-chloroquinoline
Price: 2.5g = $370.00 |
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QU551
4-Chloro-7-methylquinoline
Price: 2.5g = $375.00 |
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QU550
4-Chloro-7-methoxyquinoline
Price: 5g = $275.00 |
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QU555
4-Chloro-8-fluoroquinoline
Price: 2.5g = $240.00 |
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QU773
8-Bromo-4-chloroquinoline
Price: 2.5g = $375.00 |
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QU557
4-Chloro-8-methoxyquinoline
Price: 2.5g = $300.00 |
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4-chloro-2-methylquinolines |
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QU066
4-Chloro-6-fluoro-2-methylquinoline
Price: 2.5g = $250.00 |
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QU047
6-Bromo-4-chloro-2-methylquinoline
Price: 2.5g = $275.00 |
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QU052
4-Chloro-2,6-dimethylquinoline
Price: 2.5g = $250.00 |
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QU071
4-Chloro-6-methoxy-2-methylquinoline
Price: 2.5g = $205.00 |
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QU541
4-Chloro-6-ethoxy-2-methylquinoline
Price: 2.5g = $290.00 |
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QU536
4-Chloro-2-methyl-6-trifluoromethylquinoline
Price: 2.5g = $360.0 |
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QU547
4-Chloro-7-fluoro-2-methylquinoline
Price: 2.5g = $240.00 |
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QU468
4,7-Dichloro-2-methylquinoline
Price: 2.5g = $275.00 |
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QU736
7-Bromo-4-chloro-2-methylquinoline
Price: 1g = $205.00 |
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QU549
4-Chloro-7-methoxy-2-methylquinoline
Price: 2.5g = $290.00 |
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QU090
4-Chloro-2-methyl-7-(trifluoromethyl)quinoline
Price: 2.5g = $335.00 |
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QU554
4-Chloro-8-fluoro-2-methylquinoline
Price: 2.5g = $240.00 |
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QU556
4-Chloro-8-methoxy-2-methylquinoline
Price: 2.5g = $225.00 |
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Sandra Gemma, Giuseppe Campiani, Stefania Butini, Bhupendra P. Joshi, Gagan Kukreja, Salvatore Sanna Coccone, Matteo Bernetti, Marco Persico, Vito Nacci, Isabella Fiorini, Ettore Novellino, Donatella Taramelli, Nicoletta Basilico, Silvia Parapini, Vanessa Yardley, Simon Croft, Sonja Keller-Maerki, Matthias Rottmann, Reto Brun, Massimiliano Coletta, Stefano Marini, Giovanna Guiso, Silvio Caccia and Caterina Fattorusso
Combining 4-Aminoquinoline- and Clotrimazole-Based Pharmacophores toward Innovative and Potent Hybrid Antimalarials
Journal of Medicinal Chemistry 2009, 52, pp 502–513.
http://pubs.acs.org/doi/abs/10.1021/jm801352s
Quinoline derivatives have a long history as anti-malarial drugs. This recent paper designed hybrid quinoline/chlotrimazole compounds as heme metabolism inhibitors. The ready availability of both 4-chloro and 4-amino starting materials allowed for the selection of compounds active in chloroquine resistant strains of Plasmodium falciparum, chabaudi and berghei. An extended set of substitutions, including the ones used in the paper, are available from BioBlocks and listed below.
- R. Graham Robinett, Alex J. Freemerman, Michael A. Skinner, Lisa Shewchuk, Karen Lackey
The discovery of substituted 4-(3-hydroxyanilino)-quinolines as potent RET kinase inhibitors
Bioorganic & Medicinal Chemistry Letters 2007, 17, pp 5886–93.
Click here to access article.
In this article by scientists at GSK, quinolines were used as a core component of a series of RET kinase inhibitors, in part because of their history in marketed drugs. The availability of 2-H starting materials was important, as any substitution at the 2 position was inactive. Replacement of the 4-chloro by an aniline followed by Suzuki and Stille reactions with both aryl and heteroaryl coupling partners generated the final compounds. SAR at the 6 and 7 positions lead to the identification of leads with promising cellular activity and anticancer inhibition profiles. The key bifunctional intermediates are available from BioBlocks with and without 2-substitution.
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