Two related potent antiviral compounds: 3-bromo-N-butyl-4-butylamino-1,8-naphthalenedicarboximide (1) and 4-amino-3-bromo-N-butyl-1,8-naphthalenedicarboximide (2).
The crystal structures of two brominated derivatives of 4-amino-N-butyl-1,8-naphthalenedicarboximide [alternative systematic names: 8-bromo-2-butyl-7-butylamino-1H-benzo[de]isoquinoline-1,3(2H)-dione, C20H23BrN2O2, and 7-amino-8-bromo-2-butyl-1H-benzo[de]isoquinoline-1,3(2H)-dione, C16H15BrN2O2] are reported. The N-butyl groups, which are common to both compounds, are perpendicular to the plane of the naphthalenedicarboximide ring system. The butylamino group at position 4 in (1) is in the plane of the naphthalenedicarboximide ring, with the butyl group oriented towards the peri position of the naphthalenedicarboximide ring. This arrangement results in an opening of the (ring C)-N-(butyl C) angle.
Baughman
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Division of Science, Northeast Missouri State University, Kirksville 63501, USA.
Chang
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Utecht
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Lewis
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D000998:Antiviral Agents / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*
C094403:3-bromo-N-butyl-4-butylamino-1,8-naphthalendicarboximide; C094404:4-amino-3-bromo-N-butyl-1,8-naphthalenedicarboximide; D000998:Antiviral Agents; D009281:Naphthalenes