- Repurposing an Aldolase for the Chemoenzymatic Synthesis of Substituted Quinolines
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Quinoline derivatives are important natural products and pharmaceuticals, but their synthesis can be challenging due to poor yields, harsh reaction conditions, and instability of starting materials. Here we report the chemoenzymatic synthesis of quinaldic acids under mild conditions using an aldolase, trans-o-hydroxybenzylidenepyruvate hydratase-aldolase (NahE, or HBPA). A series of 2-aminobenzaldehydes derived from reduction of the corresponding nitro analogue were reacted with pyruvate in the presence of NahE to give substituted quinolines in up to 93% isolated yield. This reaction differs from the aldol condensation catalyzed by NahE in vivo, instead resembling the heterocycle formation catalyzed by its homologue, dihydrodipicolinate synthase.
- Fansher, Douglas J.,Granger, Richard,Kaur, Satinderpal,Palmer, David R. J.
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p. 6939 - 6943
(2021/06/28)
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- Thio hydantoin ternary and circular androgen receptor antagonists and use thereof (by machine translation)
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The invention relates to the field of pharmaceutical chemistry, and in particular relates to a category of thio hydantoin and indoline skeleton has the role of the anti-prostate cancer compound (I) and (II), a method for preparing these compounds, these c
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Paragraph 0193; 0218; 0219
(2017/08/02)
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- 6-HETEROARYLOXY- OR 6-ARYLOXY-QUINOLINE-2-CARBOXAMIDES AND METHOD OF USE
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Compounds of formula (I) and pharmaceutically acceptable salts, esters, amides, or radiolabelled forms thereof, wherein R1, R2, and R3 are as defined in the specification, are useful in treating conditions or disorders prevented by or ameliorated by voltage-gated sodium channels, e.g., Nav1.7 and/or Nav1.8. Methods for making the compounds are disclosed. Also disclosed are pharmaceutical compositions of compounds of formula (I), and methods for using such compounds and compositions.
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- Selective naphthalene H3 receptor inverse agonists with reduced potential to induce phospholipidosis and their quinoline analogs
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We reported earlier the refinement of our initial five-point pharmacophore model for the Histamine 3 receptor (H3R), with a new acceptor feature important for binding and selectivity against the other histamine receptor subtypes 1, 2 and 4. This approach was validated with a new series of H3R inverse agonists: the naphthalene series. In this Letter, we describe our efforts to overcome the phospholipidosis flag identified with our initial lead compound (1a). During the optimization process, we monitored the potency of our molecules toward the H3 receptor, their selectivity against H1R, H2R and H4R, as well as some key molecular properties that may influence phospholipidosis. Encouraged by the promising profile of the naphthalene series, we used our deeper understanding of the H3R pharmacophore model to lead us towards the quinoline series. This series is perceived to have intrinsic advantages with respect to its amphiphilic vector.
- Rodriguez Sarmiento, Rosa Maria,Nettekoven, Matthias H.,Taylor, Sven,Plancher, Jean-Marc,Richter, Hans,Roche, Olivier
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scheme or table
p. 4495 - 4500
(2010/04/05)
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- QUINOLINE DERIVATIVES AS H3R INVERSE AGONISTS
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The present invention relates to compounds of formula I: and pharmaceutically acceptable salts thereof as well as to pharmaceutical compositions comprising these compounds and to methods for their preparation. The compounds are useful for the treatment and/or prevention of diseases which are associated with the modulation of H3 receptors.
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Page/Page column 12
(2008/06/13)
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- Bicyclo 4.4.0 antiviral derivatives
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This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with amido piperazine derivatives. These compounds possess unique antiviral activity
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Page/Page column 31
(2008/06/13)
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- 1-[Acylthio) and (mercapto)-1-oxoalkyl]-1,2,3,4-tetrahydroquinoline-2-carboxylic acids
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A series of 1-[acylthio) and (mercapto)-1-oxoalkyl]-1,2,3,4-tetrahydroquinoline-2-carboxylic acids and salts thereof are useful as Angiotensin I converting enzyme inhibitors.
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