136315-25-8Relevant academic research and scientific papers
Facile Optical Resolution of a Dibenzopyrazinoazepine Derivative and the Nature of Molecular Recognition of Amines by Chiral 2,3-Di-O-(arylcarbonyl)tartaric Acids
Tomori, Hiroshi,Yoshihara, Hisayoshi,Ogura, Katsuyuki
, p. 3581 - 3590 (1996)
A facile optical resolution of racemic 1,2,3,4,10,14b-hexahydrodibenzopyrazinoazepine (1) was developed using 2,3-di-O-benzoyl-D-(-)-tartaric acid ((+)-DBT) as a resolving agent.The resolution efficiency depends remarkably on the (+)-DBT:1 ratio.When (+)-DBT and racemic 1 were mixed in methanol-water (9:1 v/v) in a 1:4 stoichiometry, a crystalline salt consisting of (+)-DBT, (R)-1, methanol, and water in a 1:2:2:2 ratio crystallized preferentially in a fair yield.X-Ray crystallographic analysis showed its highly ordered supramolecular structure: (+)-DBT molecules self-assemble via hydrogen bonding with the aid of water and methanol to form a puckered layer, and stacking of (R)-1 molecules constructs a column which is sandwiched in between the puckered layers.The X-ray crystallographic data reported for the salts that consist of amines and DBT were reinvestigated to reveal that most of the host frameworks derived from DBT have a layer structure similar to the above puckered one.
A Modular Approach to Dibenzo-fused ?-Lactams: Palladium-Catalyzed Bridging-C?H Activation
Huang, Xueliang,Ma, Liyao,Xia, Jiajin,Xin, Luoting,Yu, Yinghua,Zhu, Lei
, p. 18261 - 18266 (2020/08/21)
Tricyclic ring systems possessing a dibenzo structure joined to a seven-membered heterocyclic ring frequently show important biological activities. However, a modular approach to these molecules based on efficient intermolecular reaction of readily available chemicals is lacking. Herein, an unprecedented palladium-catalyzed formal [4+3] annulation for modular construction of these tricyclic systems is described. This reaction features easily accessible reactants (o-haloarylaldehydes and N-tosylhydrazones), broad substrate scope, and excellent functional group compatibility. The synthetic potential is demonstrated by the easy scale-up reactions, late-stage modification of complex molecules, and collective synthesis of bioactive molecules and approved drugs.
The enantioselective synthesis of (S)-(+)-mianserin and (S)-(+)-epinastine
Roszkowski, Piotr,Maurin,Czarnocki, Zbigniew
supporting information, p. 1509 - 1513 (2016/04/09)
A simple enantioselective synthetic procedure for the preparation of mianserin and epinastine in optically pure form is described. The key step in the synthetic pathway is the asymmetric reduction of the cyclic imine using asymmetric transfer hydrogenation conditions.
Hybrid approach for the design of highly affine and selective dopamine D3 receptor ligands using privileged scaffolds of biogenic amine GPCR ligands
Sasse, Britta C.,Mach, Ulrich R.,Leppaenen, Jukka,Calmels, Thierry,Stark, Holger
, p. 7258 - 7273 (2008/03/27)
A series of compounds containing privileged scaffolds of the known histamine H1 receptor antagonists cetirizine, mianserin, ketotifen, loratadine, and bamipine were synthesized for further optimization as ligands for the related biogenic amine binding dopamine D3 receptor. A pharmacological screening was carried out at dopamine D2 and D3 receptors. In the preliminary testing various ligands have shown moderate to high affinities for dopamine D3receptors, for example, N-(4-{4-[benzyl(phenyl)amino]piperidin-1-yl}butylnaphthalen-2-carboxamide (19a) (hD3 Ki = 0.3 nM; hD2 Ki = 703 nM), leading to a selectivity ratio of 2343.
14B(R) isomers of novel tetracyclic compounds having anti-allergic and anti-asthmatic activities, and their use
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, (2008/06/13)
An optically active compound of formula (I): STR1 in which R3 represents groups of formula --A--COOR4, wherein A represents alkylene groups having 3 or 5 carbon atoms and R4 represents hydrogen or an alkyl group having 1 to 4 carbon atoms; or a pharmaceutically acceptable salt thereof.
Tetracyclic compounds having anti-allergic and anti-asthmatic activities and their use
-
, (2008/06/13)
Compounds of formula (I): STR1 in which: Q is nitrogen or =CH--; R1 and R2 are hydrogen, alkyl, alkoxy, hydroxy, trifluoromethyl or halogen; and R3 is a substituted alkyl groups or a pharmaceutically acceptable salt thereof have valuable anti-allergic and anti-asthmatic activities. The compounds are prepared by reacting a corresponding compound where R3 is replaced by a hydrogen atom with a compound to introduce the group R3.
1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino-[1,2-a]azepino derivatives and 10-aza, 10-oxa and 10-thia analogues
-
, (2008/06/13)
STR1 A compound of general formula (I), wherein X=CH2, O, S or NR4, and Y=formula (II): where R1 =H, lower alkyl or an aryloxyalkyl group, wherein the aryl group is optionally substituted by alkyl, alkoxy, hydrogen, alkyl substituted by hydrogen, and n is an integer between 0 and 5, and Z=O, S or NR2 ; wherein R2 =H, lower alkyl, hydroxy, amino cyano or acyl, R3 =H, or lower alkyl, and R4 =H, lower alkyl, or lower acyl, and pharmaceutically acceptable salts thereof.
