Shuai Mu

Synthesis and Biological Evaluation of Substituted Desloratadines as Potent Arginine Vasopressin V2 Receptor Antagonists

Twenty-one non-peptide substituted desloratadine class compounds were synthesized as novel arginine vasopressin receptor antagonists from desloratadine via successive acylation, reduction and acylation reactions. Their structures were characterized by 1H-NMR and HRMS, their biological activity was evaluated by in vitro and in vivo studies. The in vitro binding assay and cAMP accumulation assay indicated that these compounds are potent selective V2 receptor antagonists. Among them compounds 1n, 1t and 1v exhibited both high affinity and promising selectivity for V2 receptors. The in vivo diuretic assay demonstrated that 1t presented remarkable diuretic activity. In conclusion, 1t is a potent novel AVP V2 receptor antagonist candidate.

2'-Carb-oxy-meth-oxy-4,4'-bis-(3-methyl-but-2-en-yloxy)chalcone.

In the title compound, C27H30O6, also known as sofalcone, an anti-ulcer agent used for the protection of gastric mucosa, the two benzene rings form a dihedral angle of 6.78 (11)°. Intermolecular O—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers, which are further linked by weak C—H⋯O interactions into ribbons propagated in [20]. Finally, π–π interactions between the benzene rings [centroid–centroid distance = 3.583 (13) Å] stabilize the crystal packing.

N-(5-Ethylsulfanyl-1,3,4-thiadiazol-2-yl)-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyri­din-5-yl)acetamide

In the title compound, C13H16N4OS3, a thienopyridinederivative, the tetrahydropyridine ring exhibits a half-chair conformation, and the folded conformation of the molecule is defined by the N—C—C—N torsion angle of −78.85 (16)°. The crystal packing features intermolecular C—H⋯N, N—H⋯N and C—H⋯O hydrogen bonds.

5-(2-Cyano-benz-yl)-4,5,6,7-tetra-hydro-thieno[3,2-c]pyridin-2-yl acetate.

In the title molecule, C17H16N2O2S, the tetrahydropyridine ring exhibits a half-chair conformation. The mean planes of the ester chain and benzene ring are twisted by 5.5 (1) and 81.32 (5)°, respectively, from the plane of thiophene ring. In the crystal, weak C—H⋯O interactions link molecules related by translation along [100] into chains.

1-[4-(3-{[5-(4-Chloro­phen­yl)furan-2-yl]methyl­idene­amino}-2,5-dioxoimidazol­idin-1-yl)but­yl]-4-methyl­piperazine-1,4-diium dichloride hemihydrate

The title compound, C23H30ClN5O3 2+·2Cl−·0.5H2O, was synthesized by N-alkylation of 1-({[5-(4-chlorophenyl)-2-furanyl]methylene}amino)-2,4-imidazolidinedione with 1-bromo-4-chlorobutane, and N-methylpiperazine. In the crystal, the cations, anions and water molecules are linked by O—H⋯Cl and N—H⋯Cl hydrogen bonds.

CCDC 799558: Experimental Crystal Structure Determination

Related Article: Shuai Mu, Miao Yang, Deng-Ke Liu, Chang-Xiao Liu|2010|Acta Crystallogr.,Sect.E:Struct.Rep.Online|66|o2762|doi:10.1107/S1600536810039085

1-[4-(4-Nitro­phen­yl)piperazin-1-yl]-2-(4,5,6,7-tetra­hydro­thieno[3,2-c]pyridin-5-yl)ethanone

The title compound, C19H22N4O3S, comprises a thienopyridine moiety which is characteristic for antiplatelet agents of the clopidogrel class of compounds. In the crystal, inversion dimers are formed through pairs of C—H⋯O interactions. The benzene ring plane and the nitro plane are almost coplanar, with a dihedral angle of 0.83 (2)°. The piperazine ring adopts a chair conformation.

(R)-[1-(2-Chloro-phen-yl)-2-meth-oxy-2-oxoeth-yl][2-(thio-phen-2-yl)eth-yl]ammonium (+)-camphor-10-sulfonate acetone monosolvate.

The title compound, C15H17ClNO2S+·C10H15O4S−·C3H6O, was synthesized by N-alkylation of α-amino-(2-chlorophenyl)acetate with 2-thienylethyl p-toluenesulfonate, followed by reaction with (+)-camphor-10-sulfonic acid. In the crystal, the cations and anions are linked through N—H⋯O hydrogen bonds. The thiophene ring of the cation was found to be disordered over two sites, with refined occupancies of 0.798 (4) and 0.202 (4).