75433-99-7Relevant articles and documents
Repurposing an Aldolase for the Chemoenzymatic Synthesis of Substituted Quinolines
Fansher, Douglas J.,Granger, Richard,Kaur, Satinderpal,Palmer, David R. J.
, p. 6939 - 6943 (2021/06/28)
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.
A quinoline -2 - formic acid and quinoline -2 - carboxylic acid derivatives of the preparation method (by machine translation)
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Paragraph 0053; 0057, (2018/08/03)
The invention discloses a quinoline - 2 - carboxylic acid and quinoline - 2 - carboxylic acid derivatives of the preparation method, the preparation method comprises the following steps: (1) 2 - furan formaldehyde after photolysis reaction to produce 5 - hydroxy furan - 2 (5 H) - one; (2) 5 - hydroxy furan - 2 (5 H) - ketone after acid hydrolysis reaction to produce 4, 4 - diethoxy - 2 - butene thiourethane; (3) 4, 4 - diethoxy - 2 - butenoic acid ethyl ester and aniline or an aniline derivative reaction, get the quinoline - 2 - carboxylic acid ethyl ester or the quinoline - 2 - carboxylic acid ethyl ester derivatives; (4) quinoline - 2 - carboxylic acid ethyl ester or the quinoline - 2 - carboxylic acid ethyl ester derivatives ester is hydrolyzed to generate quinoline - 2 - carboxylic acid or quinoline - 2 - carboxylic acid derivatives. The invention has the easy availability of raw materials, environmental pollution is small, high reaction selectivity, industrial application value is large and the like. (by machine translation)
Selective naphthalene H3 receptor inverse agonists with reduced potential to induce phospholipidosis and their quinoline analogs
Rodriguez Sarmiento, Rosa Maria,Nettekoven, Matthias H.,Taylor, Sven,Plancher, Jean-Marc,Richter, Hans,Roche, Olivier
scheme or table, p. 4495 - 4500 (2010/04/05)
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.
