Synthesis and Characterization of Aplysinopsin Analogs |
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| Authors: | James E Johnson Diana C Canseco Debra D Dolliver John A Schetz Frank R Fronczek |
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| Institution: | (1) Department of Chemistry and Physics, Texas Woman’s University, P.O. Box 425859-5859, Denton, TX 76204-5859, USA;(2) Department of Biology, Texas Woman’s University, Denton, TX 76204, USA;(3) Department of Chemistry and Physics, Southeastern Louisiana University, Hammond, LA 70402, USA;(4) Department of Pharmacology and Neuroscience, University of North Texas Health Science Center, Fort Worth, TX, USA;(5) Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA |
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| Abstract: | 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) ?, b = 8.6663(15) ?, c = 14.743(3) ?, β = 99.538(10)° at 173 K], 5-fluoroaplysinopsin DMF
solvate from 2-imino-1,3-dimethyl-imidazolidin-4-one, space group P21/c, lattice parameters a = 11.114(3) ?, b = 19.118(2) ?, c = 8.503(2) ?, β = 112.290(7)°], and 6-bromoindole-3-carboxaldehyde
(space group P21/n, lattice parameters a = 7.657(2) ?, b = 7.933(2) ?, c = 13.521(3) ?, 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-fluoroaplysinopsin exist in the E configuration.
Index Abstract Single crystal X-ray structural analyses were carried out on 5-bromo-4′-de-N-methylaplysinopsin, 5-fluoroaplysinopsin, and 6-bromoindole-3-carboxaldehyde.
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| Keywords: | Crystal structures Aplysinopsin analogs Indole alkaloids |
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