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BioBlocks Bulletin
Vol. 7 May 2009 |
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Welcome to the BioBlocks Bulletin
The BioBlocks Bulletin brings you recent research on key classes of building blocks, including quinolines, beta amino acids and heterocycles, with additional classes coming soon. Look under Application Update to view examples hand-picked by our experts, and then browse, price, and order the same products under Featured Products. Finally, product applications and product availability, all in one place!
In this issue we present
18 Fluoroquinolines.
The schemes below describe three applications of this product class to medicinal chemistry programs. Quinoline containing antimalarials are well known, but they have also been applied to other target classes including ion channels and kinases. These examples illustrate the versatility of substituted fluoroquinolines, as well as the structural types represented in our currently available catalog items, 18 of which are shown below. To view all 101 Fluoroquinolines available, download a table here.
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
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Our results-based lead optimization services focus on your project goals. Learn how our medicinal chemists can
accelerate your research
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QU1062
8-Fluoro-4-quinolinol
Price: 2.5g = $200.00 |
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QU555
4-Chloro-8-fluoroquinoline
Price: 2.5g = $210.00 |
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QU1333
6,8-Difluoro-quinolin-4-ol
Price: 1g = $200.00 |
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QU1332
5,8-Difluoro-quinolin-4-ol
Price: 1g = $255.00 |
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QU1334
7,8-Difluoro-quinolin-4-ol
Price: 500 mg = $195.00 |
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QU545
4-Chloro-6-fluoroquinoline
Price: 1g = $260.00 |
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QU1331
4-amino-6,8-difluoro-2-methylquinoline
Price: 1g = $120.00 |
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QU492
4-Amino-6-chloro-2,8-dimethylquinoline
Price: 2.5g = $600.00 |
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QU753
7-Fluoro-2-methylquinoline-3-carboxylic acid
Price: 2.5g = $600.00 |
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QU756
7-Fluoro-4-hydroxyquinoline-3-carboxylic acid
Price: 2.5g = $510.00 |
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QU714
6-Fluoro-4-hydroxyquinoline-3-carboxylic acid ethyl ester
Price: 2.5g = $180.00 |
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QU1168
4-Bromo-8-fluoro-2-methylquinoline
Price: 2.5g = $470.00 |
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QU159-1
2-Amino-6-fluoro-3-methylquinoline hydrochloride
Price: 2.5g = $390.00 |
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QU547
4-Chloro-7-fluoro-2-methylquinoline
Price: 1g = $120.00 |
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QU554
4-Chloro-8-fluoro-2-methylquinoline
Price: 1g = $120.00 |
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QU1050
6-Fluoro-2-methyl-4-quinolinol
Price: 2.5g = $80.00 |
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QU1272
7-Fluoro-2-phenyl-4-quinolinol
Price: 2.5g = $390.00 |
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QU712-1
6-Fluoro-4-hydrazino-2-methylquinoline hydrochloride
Price: 2.5g = $390.00 |
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1. Madrid, Peter B.; Sherrill, John; Liou, Ally P.; Weisman, Jennifer L.; DeRisi, Joseph L.; Guy, R. Kiplin. Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities. Bioorganic & Medicinal Chemistry Letters (2005), 15(4), 1015-1018 To view article, click here. Substituted quinolines were prepared and tested for anti-malaria activity in both chloroquine sensitive and resistant P. falciparum strains. Final compounds were generated in two steps starting from 4-hydroxy quinolines like QU1062 (scheme 1). 10 of the 4-chloroquinoline intermediates used in the paper are available from BioBlocks, as well as many other close analogs.
2. Miller, William Henry; Pearson, Neil David; Pendrak, Israil; Seefeld, Mark Andrew. Preparation of aminopiperidine derivatives for treatment of bacterial infections. WO 2003064421To view article, click here. A series of quinoline and naphthyridine containing antibacterial agents have been described by workers at GSK. Scheme 2 describes a typical synthetic scheme starting from the 6,8-difluoroquinoline QU1333. Preparation of the vinyl quinoline, through the 4-chloroquinoline intermediate, was followed by Michael addition with the racemic protected 4-amino-piperidine. Deprotection and reductive amination gave the final product. Alternatively, the 4-hydroxy group was converted to the bromomethyl ketone, then the epoxide and opened at the terminal carbon to generate hydroxyl containing analogs. Selected compounds had activity against a range of bacterial species including S. aureus, M. catarrhalis and H. influenzae. A large number of 4-hydroxy and 4-bromoquinolines, including additional difluoro isomers are currently available from BioBlocks.
3. KAWASHIMA, Tadashi; NAGAYAMA, Satoshi; NAKAO, Kazunari; TANAKA, Hirotaka. Substituted N-bicyclicalkyl Bicyclik Carboxyamide Compounds. WO 2008007211 To view article, click here. In a recent patent application from Pfizer Japan a series of quinoline and bis-quinoline amides were disclosed as VR-1 receptor antagonists. 4 aminomethylquinolines were prepared from 4 chloroquinolines as shown in scheme 3 for 4-chloro-6-fluoroquinoline. After palladium mediated cyanation, the cyano intermediate was hydrogenated under acidic conditions to the primary amine. Coupling of the acid component, also prepared in the reference, generated the final compounds.
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