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Models for potential dendritic nitric oxide donors: crystal structures of two 2‐nitroanilino precursors and nitric oxide‐release behavior of the nitrosated derivatives
Author(s) -
Badour Alec R.,
Arnett-Butscher Corey J.,
Mohanty Dillip K.,
Squattrito Philip J.,
Lambright Kelly J.,
Kirschbaum Kristin
Publication year - 2018
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229618011737
Subject(s) - chemistry , diamine , molecule , hydrogen bond , stereochemistry , amine gas treating , crystal structure , crystallography , medicinal chemistry , polymer chemistry , organic chemistry
Two molecular precursors to dendrimeric materials that could serve as slow and sustained NO‐releasing therapeutic agents have been synthesized and characterized. N 1 , N 4 ‐Bis(2‐nitrophenyl)butane‐1,4‐diamine, C 16 H 18 N 4 O 4 , (I), crystallizes in a lattice with equal populations of two molecules of different conformations, both of which possess inversion symmetry through the central C—C bond. One molecule has exclusively anti conformations along the butyl chain, while the other has a gauche conformation of the substituents on the first C—C bond. N 2 , N 2 ‐Bis[2‐(2‐nitroanilino)ethyl]‐ N 1 ‐(2‐nitrophenyl)ethane‐1,2‐diamine, C 24 H 27 N 7 O 6 , (II), crystallizes with one unique molecule in the asymmetric unit. Neighboring pairs of molecules are linked into dimers via N—H…O amine–nitro hydrogen bonds. The dimers are assembled into layers that stack in an A – B – A – B sequence such that the repeat distance in the stacking direction is over 46 Å. Molecular NO‐release agents N 1 , N 4 ‐bis(2‐nitrophenyl)‐ N 1 , N 4 ‐dinitrosobutane‐1,4‐diamine, C 16 H 16 N 6 O 6 , (III), and N 1 ‐(2‐nitrophenyl)‐ N 2 , N 2 ‐bis{2‐[(2‐nitrophenyl)(nitroso)amino]ethyl}‐ N 1 ‐nitrosoethane‐1,2‐diamine, C 24 H 24 N 10 O 9 , (IV), were prepared via treatment of (I) and (II), respectively, with NaNO 2 and acetic acid. The release of NO from solid‐phase samples of (III) and (IV) suspended in phosphate buffer was monitored spectroscopically over a period of 21 days. Although (IV) released a greater amount of NO, as expected due to it having three NO moieties for every two in (III), the (IV):(III) ratio of the rate and extent of NO release was significantly less than 1.5:1, suggesting that some combination of electronic, chemical, and/or steric factors may be affecting the release process.