Synthesis, structure and antiproliferative activity of chiral polyamines based on a 2-azanorbornane skeleton. Issue 16 (1st September 2016)

• Record Type: Journal Article
• Authors: Kamińska, Karolina; Wojaczyńska, Elżbieta; Wietrzyk, Joanna; Turlej, Eliza; Błażejczyk, Agnieszka; Wieczorek, Robert
• Is Part Of: Tetrahedron, asymmetry. Volume 27:Issue 16(2016)
• Page Start: 753
• Page End: 758
• Publication Date: 2016-09-01
• Subjects: Asymmetry (Chemistry) -- Periodicals; 547.005
• DOI: 10.1016/j.tetasy.2016.06.009
• Languages: English
• ISSNs: 0957-4166

Abstract

Graphical abstract: Abstract: A series of enantiopure 2-azanorbornane-based amines were prepared via a stereoselective aza-Diels–Alder reaction and further modifications of the obtained cycloadduct. In particular, derivatives containing two bicyclic moieties linked by NCCN fragments were synthesized. Two dimeric derivatives exhibited a significant antiproliferative activity against selected cell lines, comparable to cisplatin in certain cases. Abstract : N, N ′-Bis{[(1 S, 3 R, 4 R )-2-(( S )-1-phenylethyl)-2-azabicyclo[2.2.1]heptan-3-yl]methyl}ethan-1, 2-diamine: C32 H46 N4 [ α ]D 20 = +41.1 ( c 0.32, CH2 Cl2 ) Source of chirality: chiral substrate Absolute configuration: bis (1 S, 3 R, 4 R, 1′ S ) (by chemical correlation) Abstract : ( E )-1, 1-Diphenyl- N -{[(1 S, 3 R, 4 R )-2-(( S )-1-phenylethyl)-2-azabicyclo[2.2.1]heptan-3-yl]methylene}methanamine: C28 H30 N2 [ α ]D 20 = −24.9 ( c 0.42, CH2 Cl2 ) Source of chirality: chiral substrate Absolute configuration: (1 S, 3 R, 4 R, 1′ S ) (by chemical correlation) Abstract : ( E )-(1 S, 3 R, 4 R )-2-[( S )-1-Phenylethyl]-2-azabicyclo[2.2.1]heptan-3-al oxime: C15 H20 N2 O [ α ]D 20 = +16.9 ( c 0.26, CH2 Cl2 ) Source of chirality: chiral substrate Absolute configuration: (1 S, 3 R, 4 R, 1′ S ) (by chemical correlation) Abstract : (1 S, 3 R, 4 R )-2-[( S )-1-Phenylethyl]-3-aminemethyl-2-azabicyclo[2.2.1]heptane: C15 H22 N2 [ α ]D 20 = −26.1 ( c 0.23, CH2 Cl2 ) Source of chirality: chiral substrate Absolute configuration: (1 S, 3 R, 4 R, 1′ S ) (by chemical correlation) Abstract : N- Benzyl-bis-{[(1 S, 3 R, 4 R )-2-(( S )-1-phenylethyl)-2-azabicyclo[2.2.1]heptan-3-yl]methyl}amine: C37 H47 N3 [ α ]D 20 = +65.8 ( c 0.38, CH2 Cl2 ) Source of chirality: chiral substrate Absolute configuration: bis (1 S, 3 R, 4 R, 1′ S ) (by chemical correlation) Abstract : N -1, 1, 1-Triphenylmethyl-bis-{[(1 S, 3 R, 4 R )-2-(( S )-1-phenylethyl)-2-azabicyclo[2.2.1]heptan-3-yl]methyl}amine: C49 H55 N3 [ α ]D 20 = +57.2 ( c 0.6, CH2 Cl2 ) Source of chirality: chiral substrate Absolute configuration: bis (1 S, 3 R, 4 R, 1′ S ) (by chemical correlation) Abstract : N -Benzoyl-bis-{[(1 S, 3 R, 4 R )-2-(( S )-1-phenylethyl)-2-azabicyclo[2.2.1]heptan-3-yl]methyl}amine: C37 H45 N3 [ α ]D 20 = +69.6 ( c 0.66, CH2 Cl2 ) Source of chirality: chiral substrate Absolute configuration: bis (1 S, 3 R, 4 R, 1′ S ) (by chemical correlation) Abstract : Bis-{[(1 S, 3 R, 4 R )-2-(( S )-1-phenylethyl)-2-azabicyclo[2.2.1]heptan-3-yl]methyl}amine: C30 H41 N3 [ α ]D 20 = −13.9 ( c 0.5, CH2 Cl2 ) Source of chirality: chiral substrate Absolute configuration: bis (1 S, 3 R, 4 R, 1′ S ) (by chemical correlation)