TY - JOUR
T1 - Synthesis and characterization of aplysinopsin analogs
AU - Johnson, James E.
AU - Canseco, Diana C.
AU - Dolliver, Debra D.
AU - Schetz, John A.
AU - Fronczek, Frank R.
N1 - Funding Information:
Acknowledgements The Minority Biomedical Research Support Program of the National Institutes of Health (NIH-MBRS grant number R25-GM55380), the Robert A. Welch Foundation (grant number M-020) and the Texas Woman’s University Research Enhancement Program supported this work. This work was also supported in part by grants RO1 MH063162 and funds G67673 awarded to J.A.S. We are grateful to Dr. Wayland E. Noland at the University of Minnesota for making arrangements for us to obtain HRMS of three of the compounds reported in this paper. The purchase of the diffractometer was made possible by grant number LEQSF (1999-2000)-ENH-TR-13, administrated by the Louisiana Board of Regents.
PY - 2009/5
Y1 - 2009/5
N2 - 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.
AB - 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.
KW - Aplysinopsin analogs
KW - Crystal structures
KW - Indole alkaloids
UR - http://www.scopus.com/inward/record.url?scp=77954217060&partnerID=8YFLogxK
U2 - 10.1007/s10870-008-9480-1
DO - 10.1007/s10870-008-9480-1
M3 - Article
AN - SCOPUS:77954217060
VL - 39
SP - 329
EP - 336
JO - Journal of Chemical Crystallography
JF - Journal of Chemical Crystallography
SN - 1074-1542
IS - 5
ER -