Synthesis and characterization of aplysinopsin analogs

James E. Johnson, Diana C. Canseco, Debra D. Dolliver, John A. Schetz, Frank R. Fronczek

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Abstract

Three aplysinopsin analogs were synthesized by reacting 5-bromo-5-fluoro- and 6-bromoindole-3-carboxaldehyde with either creatinine or 2-imino-1,3-dimethyl-imidazolidin-4-one or 2-imino-1-methyl-3-ethylimidazolidin- 4-one Single crystal structures on 5-bromo-4′-de-N-methylaplysinopsin DMF solvate [from creatinine, space group P21/n, lattice parameters a = 13.117(3) Å, b = 8.6663(15) Å, c = 14.743(3) Å, β = 99.538(10)° at 173 K], 5-fluoroaplysinopsin DMF solvate [from 2-imino1,3-dimethyl-imidazolidin-4-one, space group P21/c, lattice parameters a = 11.114(3) Å, b = 19.118(2) Å, c = 8.503(2) Å, β = 112.290(7)°], and 6-bromoindole-3-carboxaldehyde (space group P21/n, lattice parameters a = 7.657(2) Å, b = 7.933(2) Å, c = 13.521(3) Å, β = 99.046(13)°) have been determined. Characterizations include spectrometric identifications employing IR, UV, HRMS, and 1H and 13C NMR. 5-Bromo-4′-de-N- methylaplysinopsin and 5-fluoroapIysinopsin exist in the E configuration.

Original languageEnglish
Pages (from-to)329-336
Number of pages8
JournalJournal of Chemical Crystallography
Volume39
Issue number5
DOIs
StatePublished - 1 May 2009

Keywords

  • Aplysinopsin analogs
  • Crystal structures
  • Indole alkaloids

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    Johnson, J. E., Canseco, D. C., Dolliver, D. D., Schetz, J. A., & Fronczek, F. R. (2009). Synthesis and characterization of aplysinopsin analogs. Journal of Chemical Crystallography, 39(5), 329-336. https://doi.org/10.1007/s10870-008-9480-1