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.
PY - 2009/5/1
Y1 - 2009/5/1
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 -