One-pot synthesis of (1RS,21SR)-diethyl 2-[23-amino-22-eth-oxy-carbonyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.0^2,7.0^15,20]penta-cosa-2,4,6,15(20),16,18,22-heptaen-25-yl]but-2-endioate.

ABSTRACT: The title compound, C₃₀H₃₄N₂O₉ (4), is a product of the Michael reaction of aza-crown ether with dimethyl acetyl-enedi-carboxyl-ate modified by an addition of NH₃ (aq.) at 298?K. The aza-14-crown-4-ether ring adopts a bowl conformation. The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 8.65?(5)°. The tetra-hydro-pyridine ring has a boat conformation. The mol-ecular conformation is supported by one N-H?O and two C-H?O intra-molecular hydrogen bonds. Both heterocyclic and amino N atoms have essentially planar configurations (sums of the bond angles are 359.35 and 358.00°). Compound 4 crystallizes as a racemate consisting of enanti-omeric pairs of the 1R,21S diastereomer. In the crystal, mol-ecules of 4 are connected by N-H?O hydrogen bonds, forming chains along [100]. According to the PASS program (computer prediction of biological activities), compound 4 may exhibit anti-allergic (72% probability) and anti-asthmatic (67%) activity, as well as be a membrane permeability inhibitor (65%).

SUBMITTER: Tran TTV 

PROVIDER: S-EPMC6127715 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature