Supplementary Information. Figure S1. 1 H NMR (600 MHz, CDCl 3 ) of 1.

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Transcription:

Supplementary Information Figure S1. 1 H NMR (600 MHz, CDCl 3 ) of 1.

Mar. Drugs 2014, 12 2 Figure S2. 13 C NMR (125 MHz, CDCl 3 ) of 1.

Mar. Drugs 2014, 12 3 Figure S3. gcosy (600 MHz, CDCl 3 ) of 1.

Mar. Drugs 2014, 12 4 Figure S4. ghsqc (600 MHz, CDCl 3 ) of 1.

Mar. Drugs 2014, 12 5 Figure S5. ghmbc (600 MHz, CDCl 3 ) of 1.

Mar. Drugs 2014, 12 6 Figure S6. 13 C NMR (125 MHz, CDCl 3 ) of 13 C-labeled 1.

Mar. Drugs 2014, 12 7 Figure S7. 13 C- 13 C COSY (125 MHz, CDCl 3 ) of 13 C-labeled 1.

Mar. Drugs 2014, 12 8 Figure S8. HRMS of 1.

Mar. Drugs 2014, 12 9 Figure S9. 1 H NMR (600 MHz, CDCl 3 ) of 2.

Mar. Drugs 2014, 12 10 Figure S10. 13 C NMR (125 MHz, CDCl 3 ) of 2.

Mar. Drugs 2014, 12 11 Figure S11. gcosy (600 MHz, CDCl 3 ) of 2.

Mar. Drugs 2014, 12 12 Figure S12. ghsqc (600 MHz, CDCl 3 ) of 2.

Mar. Drugs 2014, 12 13 Figure S13. ghmbc (600 MHz, CDCl 3 ) of 2.

Mar. Drugs 2014, 12 14 Figure S14. 13 C NMR (125 MHz, CDCl 3 ) of 13 C-labeled 2.

Mar. Drugs 2014, 12 15 Figure S15. 13 C- 13 C COSY (125 MHz, CDCl 3 ) of 13 C-labeled 2.

Mar. Drugs 2014, 12 16 Figure S16. HRMS of 2.

Mar. Drugs 2014, 12 17 Figure S17. 13 C- 13 C gcosy calculations. 1 1. During t 1, each new fid increments t 1 by a dwell time of dw1 (always true for each complex sw1 pair of FIDs, independent of type of acquisition, such as States or TPPI, etc.). For a 13 C 13 C cosy, sw = sw1 220ppm, which = 125Hz/ppm 220ppm = 27.5kHz. Thus, dw1 = 1/27.5kHz = 36.4 s. 2. For J CC ranging 30 to 60 Hz, maximum polarization transfer (largest crosspeak formation) will occur at 1/2J = 33 to 17 ms, respectively. 3. For an absolute-value cosy, where a sinebell or sinebell-squared apodization is applied, maximum crosspeaks (100% of the size of the 1 H 1D peak) will occur with a total acquisition time in the indirect dimension, at1 = 1/J, because sinebell-type functions are maximum at ½ the FID. So for maximum crosspeaks, the t 1 evolution would be at at1 = 66 to 33 ms, for J CC = 30 to 60 Hz. 4. The total acquisition time in the indirect dimension equals the number of increments times at1 sw1 the time per increment, or: at1 = ni dw1 Thus: ni TD1 = 917 to 458. dw1 Even smaller values (e.g., 256) can be used without much loss in sensitivity, since the crosspeaks intensities will follow something close to sinusoidal behavior close to 90. 5. Resolution: If ni TD1 = 400, then sw1/ni = 27500/400 = 69 Hz = 0.55 ppm @ 500 MHz. J CC

Mar. Drugs 2014, 12 18 Figure S18. 13 C- 13 C COSY pulse program (Bruker). ;cosygpqf - modified to have proton decoupling 2June2010 ;avance-version (07/04/05) ;2D homonuclear shift correlation ;using gradient pulses for selection ; ;$CLASS=HighRes ;$DIM=2D ;$TYPE= ;$SUBTYPE= ;$COMMENT= #include <Avance.incl> #include <Grad.incl> "d13=4u" "d11=30m" "in0=inf1" "d0=3u" 1 ze d11 pl12:f2 2 30m do:f2 d1 cpd2:f2 3 p1 ph1 d0 50u UNBLKGRAD p16:gp1 d16 p0 ph2 p16:gp1 d16 4u BLKGRAD go=2 ph31 30m do:f2 pl12:f2 mc #0 to 2 F1QF(id0) exit ph1=0 2 ph2=0 0 2 2 ph31=0 2 ;pl1 : f1 channel - power level for pulse (default) ;p0 : f1 channel - 20 to 90 degree high power pulse ;p1 : f1 channel - 90 degree high power pulse ;p16: homospoil/gradient pulse ;d0 : incremented delay (2D) [3 usec] ;d1 : relaxation delay; 1-5 * T1 ;d13: short delay [4 usec] ;d16: delay for homospoil/gradient recovery ;inf1: 1/SW = 2 * DW ;in0: 1/(1 * SW) = 2 * DW ;nd0: 1 ;NS: 1 * n ;DS: 16 ;td1: number of experiments ;FnMODE: QF ;use gradient ratio: gp 1 ; 10 ;for z-only gradients: ;gpz1: 10% ;use gradient files: ;gpnam1: SINE.100 ;$Id: cosygpqf,v 1.5 2007/04/11 13:34:29 ber Exp $

Mar. Drugs 2014, 12 19 Figure S19. 13 C- 13 C COSY for Varian. To set up a 13 C- 13 C gcosy on a Varian spectrometer with VNMR software, complete the following steps: 1. Set up (and acquire) a 1D 13 C spectrum with the desired parameters (sweep width, etc.) for your particular compound. 2. In the same experiment, set up a gcosy (type gcosy) 3. Your transmitter nucleus (tn) should be C13, and decoupler nucleus (dn) should be H1. 4. Type dm = nny Set number of transients and increments (nt, ni) as necessary for your compound To set up a 13 C- 13 C gcosy on a Varian spectrometer with VNMRJ software, complete the following steps: 1. Set up (and acquire) a 1D 13 C spectrum with the desired parameters (sweep width, etc.) for your particular compound. 2. In a different experiment, set up a gcosy (type Gcosy) 3. Change transmitter nucleus (tn) to C13, and decoupler nucleus (dn) should be H1. 4. Type dm = nny 5. Change sweep width (sw) and sw1 to sweep width from 1D 13 C spectrum. 6. Set number of transients and increments (nt, ni) as necessary for your compound. Set remaining parameters as the following:

Mar. Drugs 2014, 12 20 Figure S20. (A) List of 13 C- 13 C correlations for 1 and 2 and (B) 13 C- 13 C COSY (125 MHz, CDCl 3 ) of 2 (aromatic region). (A) (B) 1 2 C1-C2 C1-C2 C2-C3 C2-C3 C3-C4 * C3-C4 C8-C9 C8-C9 C9-C10 C9-C10 *** C11-C12 C11-C12 C12-C13 C12-C13 C12-C14 C12-C14 C14-C15 C14-C15 C15-C16 ** C16-C17 **** C16-C17 ** C17-C18 C17-C18 * Weak correlation. Confirmed by additional NMR data. ** C15 and C17 overlap. Additional NMR confirmed connectivity. *** C10 and C16 had similar chemical shifts. Additional NMR confirmed connectivity. **** Signal partially overlapped. Additional NMR confirmed connectivity.

Mar. Drugs 2014, 12 21 Figure S21. (A) 13 C- 13 C COSY (125 MHz, CDCl 3 ) and (B) 1 H NMR (500 MHz, CDCl 3 ) of 13 C-labeled extract from CHCl 3 partition. (A) (B)

Mar. Drugs 2014, 12 22 Figure S22. 1 H NMR (600 MHz, CDCl 3 ) of 3.

Mar. Drugs 2014, 12 23 Figure S23. 13 C NMR (125 MHz, CDCl 3 ) of 3.

Mar. Drugs 2014, 12 24 Figure S24. HRMS of 3. 2014 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).

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