Supporting Information. Discovery and Characterization of (8S, 9R)-5-Fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-
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1 Supporting Information Discovery and Characterization of (8S, 9R)-5-Fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H- 1,2,4-triazol-5-yl)-2,7,8,9-tetrahydro-3H-pyrido[4,3,2-de]phthalazin-3-one (BMN 673, talazoparib), a Novel, Highly Potent, and Orally Efficacious Poly(ADP-ribose) Polymerase- 1/2 Inhibitor as an Anticancer Agent Bing Wang,* Daniel Chu, Ying Feng, Yuqiao Shen, Mika Aoyagi-Scharber, Leonard E. Post BioMarin Pharmaceutical Inc., 105 Digital Drive, Novato, California Contents: NMR Spectra of Compound (8S,9R) S2-S5 H-NMR spectrum... S2 C13-NMR spectrum... S3 HMBC-NMR spectrum... S4 HSQC-NMR spectrum... S5 Optical Rotation Measurement for Compound (8S,9R)-47 and (8R, 9S) S6-S7 Single-crystal Structure of Compound (8S,9R) S8-S10 Single-crystal Structure of Compound (2S,3R)-60a... S11-S13 Smiles Strings..... S14-S15 Enantiomeric Purity Analysis of the Compounds in Table S16-S18 Mouse Body Weight in Xenograft Model Studies..... S19-S20 S1
2 PPM nmrb601, DMSO, F1: F2: SW1: 8224 OF1: USER: nmrb DATE: Wed Oct 28 13:19: PTS1d: EX: zg30 PW: 13.8 usec PD: 1.0 sec NA: 8 LB: 0.0 Nuts - $pdata S2
3 PPM nmrb601, DMSO, F1: F2: SW1: OF1: USER: nmrb DATE: Sun Dec 06 18:25: PTS1d: EX: zgpg30 PW: 8.1 usec PD: 2.0 sec NA: 5000 LB: 0.0 Nuts - $pdata S3
4 ppm NAME CP HMBC-DMSO T31 EXPNO 10 PROCNO 1 Date_ Time INSTRUM nmrb601 PROBHD 5 mm PABBO BB- PULPROG hmbcgpndqf TD 4096 SOLVENT DMSO NS 16 DS 16 SWH Hz FIDRES Hz AQ sec RG 203 DW usec DE 6.50 usec TE K CNST D sec D sec D sec D sec IN sec ======== CHANNEL f1 ======== NUC1 1H P usec P usec PL db PL1W W SFO MHz ======== CHANNEL f2 ======== NUC2 13C P usec PL db PL2W W SFO MHz ====== GRADIENT CHANNEL ===== GPNAM1 SINE.100 GPNAM2 SINE.100 GPNAM3 SINE.100 GPZ % GPZ % GPZ % P usec ND0 2 TD 128 SFO MHz FIDRES Hz SW ppm FnMODE QF SI 1024 SF MHz WDW SINE SSB 0 LB 0.00 Hz GB 0 PC 1.40 SI 1024 MC2 QF SF MHz WDW SINE SSB 0 LB 0.00 Hz GB ppm S4
5 ppm ppm S NAME CP HSQC-DMSO T31 EXPNO 10 PROCNO 1 Date_ Time INSTRUM nmrb601 PROBHD 5 mm PABBO BB- PULPROG hsqcedetgp TD 1024 SOLVENT DMSO NS 16 DS 16 SWH Hz FIDRES Hz AQ sec RG 203 DW usec DE 6.50 usec TE K CNST D sec D sec D sec D sec D sec D sec D sec IN sec ZGOPTNS ======== CHANNEL f1 ======== NUC1 1H P usec P usec P usec PL db PL1W W SFO MHz ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P usec P usec PCPD usec PL db PL db PL2W W PL12W W SFO MHz ====== GRADIENT CHANNEL ===== GPNAM1 SINE.100 GPNAM2 SINE.100 GPZ % GPZ % P usec ND0 2 TD 256 SFO MHz FIDRES Hz SW ppm FnMODE Echo-Antiecho SI 1024 SF MHz WDW QSINE SSB 2 LB 0.00 Hz GB 0 PC 1.40 SI 1024 MC2 echo-antiecho SF MHz WDW QSINE SSB 2 LB 0.00 Hz GB 0
6 Optical Rotation of (8S,9R)-47 Report No.: ROA_ L04 Project Code: L04 Sample ID: Remark Rotation Wavelength Cell Path 589 nm 100 mm Specific Rotation Temperature 20 MeOH:CAN:DMF=0.5:0.5: Solvent 1 Instrument RUDOLPH (AUTOPOL V) Automatic Polarimeter Concentration 0.667g/100ml (6.67mg/ml) S6
7 Optical Rotation of (8R,9S)-47 Report No.: ROA_ L04 Project Code: L04 Sample ID: Remark Rotation Wavelength Cell Path 589 nm 100 mm Specific Rotation Temperature 20 MeOH:ACN:DMF=0.5:0.5: Solvent 1 Instrument RUDOLPH (AUTOPOL V) Automatic Polarimeter Concentration 0.667g/100ml (6.67mg/ml) S7
8 ORTEP drawing of (8S,9R)-47 Tosylate (LIMS no ). Atoms are represented by 50% probability anisotropic thermal ellipsoids. S8
9 I. Crystal Data and Data Collection Parameters for (8S,9R)-47 Tosylate formula C 26H 22F 2N 6O 4S formula weight space group P2 1 (No. 4) a, Å (11) b, Å (9) c, Å (10) β, deg (6) V, Å (2) Z 2 d calc, g cm crystal dimensions, mm 0.20 x 0.18 x 0.01 temperature, K 150. radiation (wavelength, Å) Cu K α ( ) monochromator graphite linear abs coef, mm absorption correction applied empirical a transmission factors: min, max 0.643, diffractometer Rigaku Rapid II h, k, l range -14 to 14-7 to to 14 2θ range, deg mosaicity, deg 0.84 programs used SHELXTL F weighting 1/[σ 2 (F o2 )+(0.0293P) P] where P=( F o2 +2F c2 )/3 data collected unique data 4037 R int data used in refinement 4037 cutoff used in R-factor calculations F o2 >2.0σ(F o2 ) data with I>2.0σ(I) 2384 refined extinction coef number of variables 428 largest shift/esd in final cycle 0.00 R(F o) R w(f o2 ) goodness of fit absolute structure determination Flack parameter b (0.04(2)) Hooft parameter c (0.056(19)) Friedel Coverage 82% a CrystalClear: An Integrated Program for the Collection and Processing of Area Detector Data, Rigaku Corporation, b Flack,H. D. Acta Cryst., 1983 A39, 876. c Hooft,R.W.W., Straver,L.H., and Spek, A.L. J. Appl. Cryst., 2008, 41, S9
10 Positional Parameters and Their Estimated Standard Deviations for (8S,9R)-47 Tosylate Atom x y z U(Å 2 ) S (10) (15) (9) (4) F (19) (3) (18) (8) F (2) (3) (2) (11) O (2) (4) (2) (12) O (2) (4) (2) (10) O (3) (4) (3) (10) O (2) (4) (2) (9) N (3) (5) (3) (12) N (3) (5) (3) (14) N (3) (5) (3) (12) N (3) (5) (3) (12) N (3) (6) (3) (12) N (4) (5) (3) (14) C (4) (7) (3) (16) C (4) (7) (3) (16) C (4) (6) (3) (14) C (4) (6) (4) (16) C (4) (6) (4) (17) C (4) (6) (4) (16) C (4) (6) (3) (14) C (4) (6) (4) (16) C (3) (6) (3) (16) C (3) (5) (3) (10)* C (4) (6) (3) (14) C (5) (7) (4) (19) C (4) (7) (4) (19) C (4) (7) (4) (17) C (5) (7) (4) 0.045(2) C (4) (6) (3) (16) C (4) (6) (3) (16) C (5) (6) (4) (19) C (5) (7) (5) 0.052(2) C (5) (8) (5) 0.059(2) C (5) (9) (5) 0.060(2) C (5) (7) (4) 0.047(2) C (7) (19) (9) 0.095(4) C (4) (7) (3) (16) C (5) (6) (5) 0.052(2) C (4) (7) (4) (17) H (3) 0.456(5) 0.294(3) 0.032(14)* H (3) 0.146(5) 0.388(3) 0.029(12)* H (3) 0.308(5) 0.511(3) 0.039(13)* H (3) 0.352(4) 0.498(3) 0.023(11)* H (3) 0.348(6) 0.193(3) 0.056(15)* Starred atoms were refined isotropically U eq = (1/3)Σ iσ j U ija * ia * ja i.a j Hydrogen atoms are included in calculation of structure factors but not refined S10
11 ORTEP drawing of (2S,3R)-60a. Atoms are represented by 50% probability anisotropic thermal ellipsoids. S11
12 Crystal Data and Data Collection Parameters for Compound (2S,3R)-60a formula C 20H 16F 2N 4O 3 formula weight space group P (No. 96) a, Å (2) c, Å (3) V, Å (3) Z 8 d calc, g cm crystal dimensions, mm 0.20 x 0.20 x 0.04 temperature, K 150. radiation (wavelength, Å) Cu K α ( ) monochromator graphite linear abs coef, mm absorption correction applied empirical a transmission factors: min, max 0.769, diffractometer Rigaku Rapid II h, k, l range -9 to 8-6 to to 55 2θ range, deg mosaicity, deg 2.87 programs used SHELXTL F weighting 1/[σ 2 (F o2 )+(0.0461P) P] where P=( F o2 +2F c2 )/3 data collected unique data 3252 R int data used in refinement 3252 cutoff used in R-factor calculations F o2 >2.0σ(F o2 ) data with I>2.0σ(I) 2691 refined extinction coef number of variables 327 largest shift/esd in final cycle 0.00 R(F o) R w(f o2 ) goodness of fit absolute structure determination Flack parameter b (-0.1(2)) Hooft parameter c (-0.08(11)) Friedel Coverage 100% a CrystalClear: An Integrated Program for the Collection and Processing of Area Detector Data, Rigaku Corporation, b Flack,H. D. Acta Cryst., 1983 A39, 876. c Hooft,R.W.W., Straver,L.H., and Spek, A.L. J. Appl. Cryst., 2008, 41, S12
13 Positional Parameters and Estimated Standard Deviations for Compound (2S,3R)-60a Atom x y z U(Å 2 ) F (19) (19) (3) (5) F (19) (19) (3) (5) O (2) (2) (3) (6) O (2) (2) (4) (6) O (2) (2) (4) (6) N (3) (3) (4) (7) N (3) (3) (4) (6) N (3) (3) (5) (8) N (3) (3) (4) (7) C (3) (3) (5) (8) C (3) (4) (5) (8) C (3) (3) (5) (8) C (3) (3) (5) (7) C (3) (3) (5) (7) C (3) (3) (5) (7) C (3) (3) (5) (7) C (3) (3) (5) (8) C (3) (3) (5) (8) C (5) (4) (9) (10) C (3) (3) (6) (8) C (3) (3) (5) (7) C (4) (4) (6) (9) C (5) (4) (8) (12) C (3) (3) (5) (7) C (3) (3) (5) (8) C (4) (3) (6) (8) C (3) (3) (5) (8) C (3) (3) (6) (9) C (3) (3) (5) (8) H (4) 0.783(5) (7) 0.091(13)* H (3) 0.785(3) (5) 0.038(8)* H (3) 0.687(3) (5) 0.023(7)* H (3) 0.414(3) (5) 0.035(8)* H (3) 0.500(3) (6) 0.045(8)* H (4) 0.424(3) (6) 0.068(10)* H (3) 0.826(3) (6) 0.052(9)* H (4) 0.879(4) (6) 0.061(10)* H (4) 0.593(4) (6) 0.061(10)* H (4) 0.536(4) (5) 0.054(9)* H10A 1.058(4) 0.159(4) (7) 0.071(11)* H10B 1.185(4) 0.243(4) (6) 0.061(10)* H10C 1.068(4) 0.142(4) (7) 0.071(12)* H14A 0.770(5) 0.080(5) (9) 0.116(16)* H14B 0.739(5) 0.103(5) (8) 0.106(15)* H14C 0.625(6) 0.184(6) (9) 0.131(19)* Starred atoms were refined isotropically U eq = (1/3)Σ iσ j U ija * ia * ja i.a j Hydrogen atoms are included in calculation of structure factors but not refined S13
14 Compound Smiles PARP-1 Enzyme Cellular PAR TMZ Chemosensitizationᵈ Capan-1 rlm IC₅₀ (nm)ᵃ inhibition GI₅₀ (µm)ᵇ (BRCA2 mutant) T1/2 EC₅₀ (nm)ᵇ EC₅₀ (µm)ᵇ (min)ᵃ 13 O=C1NN=C2C(C3=CC=CC=C3)C(C4=CC=CC=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=CC=C(CN(C)C)C=C3)C(C4=CC=CC=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=CC=CC=C3)C(C4=CC=C(CN(C)C)C=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=CC=CC(CN(C)C)=C3)C(C4=CC=CC=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=CC=CC=C3)C(C4=CC(CN(C)C)=CC=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=CC=C(CN(C)C)C=C3)C(C4=CC=C(CN(C)C)C=C4)NC5=CC=CC1=C > O=C1NN=C2C(C3=CC=C(C(C)C)C=C3)C(C4=CC=C(CN(C)C)C=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=CC=C(C)C=C3)C(C4=CC=C(CN(C)C)C=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=CC=C(C(F) (F)F)C=C3)C(C4=CC=C(CN(C)C)C=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=CC=C(F)C=C3)C(C4=CC=C(CN(C)C)C=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=CC=CC=C3)C(C4=CC=C(CN(C)C)C=C4)NC5=CC(F)=CC1=C O=C1NN=C2C(C3=CC=C(F)C=C3)C(C4=CC=C(CN(C)C)C=C4)NC5=CC(F)=CC1=C O=C1NN=C2C(C3=CC=CC=C3)C(C4=CC=C(CN5CCN(C)CC5)C=C4)NC6=CC=CC1=C O=C1NN=C2C(C3=CC=CC=C3)C(C4=CC=C(CN5CCCC5)C=C4)NC6=CC=CC1=C O=C1NN=C2C(C3=CC=CC=C3)C(C4=CC=C(CN5CCC5)C=C4)NC6=CC=CC1=C O=C1NN=C2C(C3=CC=C(F)C=C3)C(C4=CC=C(CN5CCCC5)C=C4)NC6=CC=CC1=C O=C1NN=C2C(C3=CC=C(F)C=C3)C(C4=CC=C(CN5CCC5)C=C4)NC6=CC=CC1=C O=C1NN=C2C(C3=CC=NC=C3)C(C4=CC=NC=C4)NC5=CC=CC1=C > O=C1NN=C2C(C3=CC=CC=N3)C(C4=CC=CC=N4)NC5=CC=CC1=C O=C1NN=C2C(C3=CC=CN=C3)C(C4=CN=CC=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=NC=CN3C)C(C4=NC=CN4C)NC5=CC=CC1=C O=C1NN=C2C(C3CCCNC3)C(C4=CN=CC=C4)NC5=CC=CC1=C O=C1NN=C2C(C(C)C)C(C3=CC=CC=C3)NC4=CC=CC1=C O=C1NN=C2C(C3=CC=CC=C3)C(C4=NC=CN4C)NC5=CC=CC1=C > O=C1NN=C2C(C3=NC=CN3C)C(C4=CC=CC=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=NC=CN3C)C(C4=CC=C(F)C=C4)NC5=CC=CC1=C > O=C1NN=C2C(C3=NC=CN3C)C(C4=CC=CC=C4)NC5=CC(F)=CC1=C O=C1NN=C2C(C3=NC=CS3)C(C4=CC=C(F)C=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=CC=NN3C)C(C4=CC=C(F)C=C4)NC5=CC=CC1=C > O=C1NN=C2C(C3=NC=CN3C)C(C4=CC=C(C(F)(F)F)C=C4)NC5=CC=CC1=C O=C1NN=C2C(C3=NC=CN3C)C(C4=CC=CC=C4)NC5=CC(Cl)=CC1=C O=C1NN=C2C(C3=NC=CN3C)C(C4=CC=C(F)C=C4)NC5=CC(F)=CC1=C O=C1NN=C2C(C3=NC=NN3C)C(C4=CC=CC=C4)NC5=CC=CC1=C > O=C1NN=C2C(C3=NC=NN3C)C(C4=CC=CC=C4)NC5=CC(F)=CC1=C O=C1NN=C2C(C3=NN=CN3C)C(C4=CC=CC=C4)NC5=CC=CC1=C > O=C1NN=C2C(C3=NC=NN3C)C(C4=CC=C(F)C=C4)NC5=CC=CC1=C > O=C1NN=C2C(C3=NC=NN3C)C(C4=CC=C(F)C=C4)NC5=CC(F)=CC1=C O=C1NN=C2C(C3=NC=NN3C)C(C4=CC=C(NC(C)=O)C=C4)NC5=CC(F)=CC1=C > O=C1NN=C2C(C3=NC=NN3C)C(C4=CN=CN=C4)NC5=CC(F)=CC1=C O=C1NN=C2C(C3=NC=NN3C)C(C4=CC=NN4C)NC5=CC(F)=CC1=C O=C1NN=C2C(C3=NC=NN3C)C(C4=CC=C(C#N)C=C4)NC5=CC(F)=CC1=C (Rucaparib) FC1=CC2=C3C(NC(C4=CC=C(CNC)C=C4)=C3CCNC2=O)=C ᵃ Mean of duplicate determinations. ᵇ Mean of triplicate determinations. ᵈ TMZ sensitization condition: the concentration (µm) of TMZ that kills 50% of the treated cells (GI50) in the presence of 0.4 µm of PARP inhibitors S14
15 Compound Smiles PARP-1 Cellular PAR TMZ Chemo- Capan-1 Enzyme inhibition sensitizationᵈ (BRCA2 deficient) IC₅₀ (nm)ᵃ EC₅₀ (nm)ᵇ GI₅₀ (µm)ᵇ EC₅₀ (nm)ᵇ (8R,9S) > 10, (8S,9R) (8R,9S) (8S,9R) (8S,9R) (8R,9S) (8S,9R) (8R,9S) (8S,9R) (8R,9S)-47 O=C1NN=C2[C@@H](C3=NC=NN3C)[C@H](C4=CC=C(F)C=C4)NC5=CC(F)=CC1=C ᵃ Mean of duplicate determinations. ᵇ Mean of triplicate determinations. ᵈ TMZ sensitization condition: the concentration (nm) of a PARP inhibitor that kills 50% of the treated cells (GI50) in the presence of 200 µm of TMZ is reported. S15
16 Enantiomeric Purity Analysis of the Compounds in Table 3 S16
17 Enantiomeric Purity Analysis of the Compounds in Table 3 (cont d) S17
18 Enantiomeric Purity Analysis of the Compounds in Table 3 (cont d) S18
19 S19
20 S20
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