One-pot synthesis of (1RS,21SR)-diethyl 2-[23-amino-22-eth­oxy­carbonyl-8,11,14-trioxa-25-aza­tetra­cyclo­[19.3.1.02,7.015,20]penta­cosa-2,4,6,15(20),16,18,22-heptaen-25-yl]but-2-endioate

Acta Crystallographica Section E: Crystallographic Communications

Tran, T.T.V.¹  Truong, H.H.²  Le, T.A.³ 

[1] Faculty of Chemistry, University of Science, Vietnam National University, 19 Le Thanh Tong, Hoan Kiem, Hanoi, Vietnam;Inorganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian Federation;Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian Federation

关键词: MACROHETEROCYCLES;    AZACROWN ETHER;    ONE-COMPONENT REACTION;    CYTOTOXICITY;    ANTICANCER ACTIVITY;    CRYSTAL STRUCTURE;   

DOI  :  10.1107/S205698901801160X

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

The title compound, C30H34N2O9 (4), is a product of the Michael reaction of aza­crown ether with dimethyl acetyl­enedi­carboxyl­ate 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 tetra­hydro­pyridine ring has a boat conformation. The mol­ecular conformation is supported by one N—H⋯O and two C—H⋯O intra­molecular 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 enanti­omeric pairs of the 1R,21S diastereomer. In the crystal, mol­ecules 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 anti­allergic (72% probability) and anti­asthmatic (67%) activity, as well as be a membrane permeability inhibitor (65%).

【 授权许可】

CC BY