Structure-Activity Relationship for the Oxadiazole Class of Antibiotics. Supporting Information
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1 Structure-Activity Relationship for the xadiazole Class of Antibiotics Edward Spink, Derong Ding, Zhihong Peng, Marc A. Boudreau, Erika Leemans, Elena Lastochkin, Wei Song, Katerina Lichtenwalter, Peter I. Daniel, Sebastian A. Testero, Hualiang Pi, Valerie A. Schroeder, William R. Wolter, uno T. Antunes, Mark A. Suckow, Sergei Vakulenko, Mayland Chang *, Shahriar Mobashery * Department of Chemistry and Biochemistry, University of otre Dame, otre Dame, I 46556, USA. Freimann Life Sciences Center and Department of Biological Sciences, University of Authors contributed equally to this work otre Dame, otre Dame, I 46556, USA Supporting Information Contents Experimental Procedures... 2 Table S1. Spectral data of final compounds... 3 Table S2. Minimal Inhibitory concentrations (MICs)... 29
2 Experimental Procedures General procedure for synthesis of benzoyl chlorides This has been previously described. 1 General procedure for synthesis of heteroaryl acyl chlorides The carboxylic acid (1.0 equiv) was dissolved in thionyl chloride (25.0 equiv), and the mixture was heated to reflux for 2.5 h. The excess thionyl chloride was removed in vacuo, and the resulting solid was used without further purification. General procedure for synthesis of diphenyl ethers, Method A (nucleophilic aromatic substitution) A 4-fluorobenzonitrile derivative (1.0 equiv.), a phenol derivative (1.0 equiv.), and K 2 C 3 (2.0 equiv.) were dissolved in either DMS or DMF, and the mixture was stirred at 100 o C for 16 h. The mixture was cooled to room temperature and was diluted with water (2x volume of DMS or DMF used), then it was extracted with ethyl acetate (3x). The combined organic layer was washed with water (3x), then once with brine, and dried (anhydrous a 2 S 4 ). After being concentrated in vacuo, the crude material was purified by column chromatography on silica gel. General procedure for synthesis of diphenyl ethers, Method B (Ullmann coupling) This has been previously described. 1 General procedure for nitro reduction using Fe/HCl This has been previously described. 1 General procedure for nitro reduction using SnCl 2 H 2 Using an adaptation of a literature procedure, 2 the starting material (1.0 equiv.) was dissolved in ethanol (6.0 ml/mmol starting material), and SnCl 2 2H 2 (5.0 equiv.) was added. The mixture was stirred at 70 o C for 4 h, then cooled to room temperature and poured onto ice. The ph was adjusted to ~7-8 with saturated ahc 3, and the aqueous layer was extracted 3x with ethyl
3 acetate. The combined organic layers were dried (anhydrous a 2 S 4 ), and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel. General procedure for synthesis of -hydroxybenzimidamides This was previously described. 1 General procedure for synthesis of allyl-protected phenols Allyl-protected phenols 9, 3 12, 4 13, 5 and 20, 6 are known compounds, and were synthesized using previously described procedures. 3 Compounds 52, 14, and 15 were synthesized using previously described procedures. 1,7 Table S1. Spectral data of final compounds Compound umber 57a Structure and data 57b Lit. 1 57c Lit F MR (500 MHz, DMS-d 6 ) δ 6.99 (d, J = 8.6 Hz, 2H), 7.14 (d, J = 8.6 Hz, 2H), (m, 2H), (m, 2H), 8.02 (d, J = 8.6 Hz, 2H), 8.06 (d, J = 8.6 Hz, 2H). (125 MHz, DMS-d 6 ) δ 114.1, 116.3, (d, J CF = 23.3 Hz), 117.8, 121.0, (d, J CF = 8.6 Hz), 129.2, 130.1, 151.3, (d, J CF = Hz), 160.1, 162.1, 167.5, (282 MHz, DMS-d 6 ) δ calcd for C 21 H 14 F , found [MH] +
4 58 58a (600 MHz, CDCl 3 ) δ 4.13 (s, 2H), 6.71 (d, J = 8.5 Hz, 2H), (m, 6H), 8.00 (d, J = 8.5 Hz, 2H), 8.11 (d, J = 8.5 Hz, 2H). (125 MHz, DMS-d 6 ) δ 114.0, 114.5, 116.6, 117.8, 121.3, 122.0, 129.3, 130.0, 150.6, 151.9, 158.3, 160.2, 168.1, calcd for C 20 H 15 F , found [MH] + 58b (600 MHz, acetone-d 6 ) δ 5.63 (br s, 2H), 6.84 (d, J = 8.8 Hz, 2H), 7.13 (d, J = 7.5 Hz, 2H), 7.14 (d, J = 8.8 Hz, 2H), 7.22 (t, J = 7.5 Hz, 1H), 7.45 (t, J = 7.5 Hz, 2H), 7.92 (d, J = 8.8 Hz, 2H), 8.13 (d, J = 8.8 Hz, 2H). (150 MHz, acetone-d 6 ) δ 112.4, 114.8, 119.2, 120.6, 123.2, 125.2, 130.0, 130.7, 131.1, 154.2, 157.2, 161.0, 168.7, calcd for C 20 H , found [MH] + 58c Lit F MR 59b (600 MHz, CDCl 3 ) δ 4.13 (s, 2H), 6.71 (d, J = 8.5 Hz, 2H), (m, 6H), 8.00 (d, J = 8.5 Hz, 2H), 8.11 (d, J = 8.5 Hz, 2H). (125 MHz, DMS-d 6 ) δ 114.0, 114.5, 116.6, 117.8, 121.3, 122.0, 129.3, 130.0, 150.6, 151.9, 158.3, 160.2, 168.1, (282 MHz, CDCl 3 ) δ calcd for C 20 H 15 F , found [MH] + ClH 3 CF 3
5 60a 60b 60c 61a (400 MHz, DMS-d 6 ) δ 5.90 (br s, 3H), 6.81 (d, J = 8.6 Hz, 2H), 7.28 (d, J = 9.0 Hz, 2H), 7.29 (d, J = 8.6 Hz, 2H), 7.79 (d, J = 8.6 Hz, 2H), 7.88 (d, J = 8.6 Hz, 2H), 8.11 (d, J = 9.0 Hz, 2H). (100 MHz, DMS-d 6 ) δ 110.7, 114.5, 119.1, 119.8, (q, J CF = Hz), (q, J CF = 32.5 Hz), (q, J CF = 3.8 Hz), 129.3, 129.6, 157.9, 159.3, 167.2, calcd for C 21 H 14 F , found [MH] + H (400 MHz, DMS-d 6 ) δ (m, 4H), 7.26 (t, J = 7.4 Hz, 1H), 7.48 (t, J = 7.6 Hz, 2H), 8.11 (d, J = 8.4 Hz, 1H), 8.39 (s, 1H), (s, 1H). (100 MHz, DMS-d 6 ) δ 110.3, 118.3, 119.7, 120.6, 124.5, 129.3, (2C), 133.5, 155.4, 159.8, 167.5, calcd for C 17 H 11 Cl , found [MH] + H (400 MHz, CDCl 3 ) δ (m, 4H), 7.66 (d, J = 8.8 Hz, 2H), 8.02 (s, 1H), (m, 2H), (br s, 1H). (100 MHz, DMS-d 6 ) δ 110.8, 119.8, 120.6, 122.6, 124.8, 125.1, (q, J CF = 3.6 Hz), 130.1, 130.9, 134.1, 158.8, 159.9, 168.0, calcd for C 18 H 11 ClF , found [MH] + H Cl Cl Cl (400 MHz, CDCl 3 ) δ (m, 6H), 7.91 (s, 1H), 8.16 (d, J = 9.2 Hz, 2H). (100 MHz, DMS-d 6 ) δ 110.1, 116.8, 117.0, 117.9, 120.6, 121.8, 121.9, 129.3, 130.3, 133.5, 151.2, 151.3, 157.6, 160.0, 160.2, 167.4, calcd for C 17 H 11 ClF , found [MH] + CF 3 F
6 61b (400 MHz, CDCl 3 ) δ (m, 4H), (m, 1H), (m, 2H), 7.97 (s, 1H), (m, 2H). (100 MHz, DMS-d 6 ) δ 94.1, 117.9, 118.4, 119.7, 120.6, 124.5, 129.3, 130.0, 130.3, 132.7, 155.4, 159.8, calcd for C 17 H 12 Br , found [MH] + 62a (400 MHz, DMS-d 6 ) δ (m, 4H), 7.80 (d, J = 8.8 Hz, 2H), (m, 2H), 8.38 (s, 1H). (100 MHz, DMS-d 6 ) δ 94.2, 119.1, 120.0, 122.0, 124.1, 124.4, (q, J CF = 3.6), 129.5, 132.7, 135.1, 158.2, 159.2, 167.4, calcd for C 18 H 11 BrF , found [MH] + 62b 63a (400 MHz, CDCl 3 ) δ (m, 4H), (m, 1H), (m, 2H), 8.05 (s, 1H), (m, 2H). (100 MHz, DMS-d 6 ) δ 60.7, 119.0, 120.3, 121.2, 125.3, 129.9, 131.0, 138.2, 138.9, 156.0, 160.5, 168.1, calcd for C 17 H 12 I , found [MH] + H I (400 MHz, DMS-d 6 ) δ (m, 4H), 7.80 (d, J = 8.8 Hz, 2H), 8.16 (d, J = 8.4 Hz, 2H), 8.31 (s, 1H). (100 MHz, DMS-d 6 ) δ 60.4, 119.1, 120.0, 122.1, 122.8, 124.1, 124.4, 125.5, (q, J CF = 3.5 Hz), 129.4, 137.4, 138.3, 158.1, 159.2, 167.3, calcd for C 18 H 11 F 3 I , found [MH] + 2 CF 3 H
7 63c (400 MHz, CD 3 D) δ (m, 4H), (m, 1H), (m, 2H), (m, 2H), 8.82(s, 1H). (100 MHz, DMS-d 6 ) δ 119.0, 120.5, 120.8, 125.3, 130.0, 131.0, 133.0, 134.8, 155.9, 160.8, 168.4, calcd for C 17 H , found a 64c (500 MHz, DMS-d 6 ) δ (m, 6H), 8.08 (t, J = 8.8 Hz, 2H), 9.2 (s, 1H). (100 MHz, DMS-d 6 ) δ 116.8, 117.0, 117.9, 120.1, 122.0, 129.3, 132.5, 134.1, 151.2, 157.7, 160.1, 160.4, 167.7, calcd for C 17 H 11 F , found [MH] + H H 2 (400 MHz, CDCl 3 ) δ 4.31 (br s, 2H), (m, 4H), (m, 1H), (m, 3H), (m, 2H). (100 MHz, DMS-d 6 ) δ 115.1, 118.3, 119.7, 121.0, 124.3, 124.5, 129.3, 130.3, 133.8, 155.5, 159.7, 166.8, calcd for C 17 H [M+H] , found a (400 MHz, CDCl 3 ) δ 6.79 (d, J = 8.8 Hz, 2H), (m, 4H), 7.21 (s, 1H), 7.76 (d, J = 8.8 Hz, 2H). (400 MHz, CDCl 3 ) δ 116.7, 116.9, 117.5, 118.1, 121.0, 121.6, 121.7, 124.1, 129.3, 132.3, 151.6, 151.7, 158.3, 160.4, 160.7, 167.4, calcd for C 17 H 13 F , found [MH] + H H
8 67b (400 MHz, CDCl 3 ) δ 1.32 (s, 3H), 1.33 (s, 3H), (m, 1H), (m, 4H), (m, 1H), (m, 2H), 7.49 (s, 1H), (m, 2H) (100 MHz, CDCl 3 ) δ 23.2, 47.8, 115.9, 118.4, 120.0, 121.5, 123.0, 124.4, 129.5, 130.1, 135.5, 156.2, 160.5, 167.8, calcd for C 20 H [M+H] , found b (400 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 2H), 8.33 (s, 1H). (100 MHz, DMS-d 6 ) δ 95.4, 111.4, 119.3, 119.8, 121.7, 126.1, 126.4, (q, J CF = 4 Hz), 130.0, 137.4, 139.4, 159.3, 159.5, 167.9, calcd for C 19 H 11 F , found [MH] + 69c (400 MHz, DMS-d 6 ) δ 6.96 (d, J = 8.4 Hz, 1H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 2H). (100 MHz, DMS-d 6 ) δ 114.9, 115.4, 117.0, 119.8, 120.5, 121.2, 123.2, 123.5, 124.8, 125.1, 126.2, 126.3(q, J = 3.6 Hz), 130.0, 146.6, 151.4, 158.7, 160.0, 168.1, calcd for C 21 H 13 F , found [MH] + 70a (400 MHz, DMS-d 6 ) δ 6.95 (d, J = 8.4 Hz, 1H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), 9.68 (br s, 1H), (br s, 1H). (100 MHz, DMS-d 6 ) δ 114.3, 114.7, 116.3, 116.8, 117.0, 117.8, 120.5, 121.1, 121.8, 121.9, 129.2, 146.0, 150.7, 151.3, 151.4, 157.6, 160.0, 167.5, calcd for C 20 H 14 F , found [MH] +
9 70c (500 MHz, CDCl 3 ) δ (m, 3H), 7.14 (t, J = 8.5 Hz, 1H), 7.18 (t, J = 7.4 Hz, 1H), (m, 3H), (m, 2H), 8.11 (d, J = 8.8 Hz, 2H). calcd for C 20 H 14 F , found [MH] + 19 F MR 71c (500 MHz, CD 3 D) δ 7.03 (d, J = 9.0 Hz, 2H), (m, 3H), (m, 2H), (m, 2H), 8.04 (d, J = 9.0 Hz, 2H). (125 MHz, DMS-d 6 ) δ 116.0, 117.0, 117.7, 118.9, 119.6, 122.8, 122.9, 126.5, 130.4, 151.4, 152.9, 153.4, 161.0, 162.2, 169.6, (282 MHz, CD 3 D) δ , calcd for C 20 H 13 F , found [MH] + 19 F MR 72a (500 MHz, CD 3 D) δ 7.09 (d, J = 8.5 Hz, 2H), (m, 4H), 7.78 (d, J = 8.5 Hz, 2H), 8.10 (d, J = 9.0 Hz, 2H). (125 MHz, CD 3 D) δ 113.1, (t, J CF = 9.6 Hz), (d, J CF = 23.8 Hz), 119.0, 122.6, (d, J CF = 8.3 Hz), 130.5, 140.6, (dd, J CF = 242.8, 7.0 Hz), (d, J CF = 2.5 Hz), (d, J CF = Hz), 162.3, 169.8, (282 MHz, CD 3 D) δ , calcd for C 20 H 12 F , found [MH] + 19 F MR (500 MHz, CDCl 3 ) δ 4.23 (br s, 2H), 6.85 (t, J = 8.6 Hz, 1H), (m, 4H), 7.17 (t, J = 7.4 Hz, 1H), 7.38 (dd, J = 8.6, 7.6 Hz, 2H), (m, 2H), 8.10 (d, J = 9.0 Hz, 2H). (125 MHz, CDCl 3 ) δ (d, J CF = 8.2 Hz), (d, J CF = 20.6 Hz), (d, J CF = 3.3 Hz), 118.5, 119.9, 121.9, 124.3, (d, J CF = 3.3 Hz), 129.4, 130.1, (d, J CF = 12.3 Hz), (d, J CF = Hz), 156.3, 160.2, 168.4, (282 MHz, CDCl 3 ) δ (dd, J = 11.0, 8.6 Hz).
10 calcd for C 20 H 15 F , found [MH] + 72b 19 F MR 73b 74a 75a (500 MHz, CDCl 3 ) δ 4.25 (br s, 2H), 6.85 (t, J = 8.6 Hz, 1H), (m, 4H), 7.62 (d, J = 8.6 Hz, 2H), (m, 2H), 8.16 (d, J = 8.8 Hz, 2H). (125 MHz, CDCl 3 ) δ (d, J CF = 8.2 Hz), (d, J CF = 21.4 Hz), (d, J CF = 4.1 Hz), 118.9, 119.7, 123.3, (q, J CF = Hz), (d, J CF = 2.5 Hz), (q, J CF = 32.9 Hz), 129.7, (d, J CF = 12.3 Hz), (d, J CF = Hz), 158.6, (d, J CF = 1.6 Hz), 168.3, (d, J CF = 2.5 Hz). (282 MHz, CDCl 3 ) δ (dd, 1F, J = 12.2, 8.6 Hz), (s, 3F). H F (400 MHz, CDCl 3 ) δ (m, 4H), 7.64 (d, J = 8.5 Hz, 2H), 7.78 (dd, J = 6.7, 1.5 Hz, 2H), 8.16 (d, J = 9.0 Hz, 2H). (100 MHz, CDCl 3 ) δ (m), 119.0, 119.7, 122.8, 124.8, (q, J CF = 32.9 Hz) (q, J CF = 3.8 Hz), 129.7, 138.2, (d, J CF = 15.8 Hz), 148.1, (dd, J CF = 244.4, 6.8 Hz), 158.9, calcd for C 21 H 11 F , found [MH] + H F (400 MHz, CDCl 3 ) δ 4.18 (s, 2H), 6.36 (s, 1H), 6.74 (d, J = 8.6 Hz, 2H), (m, 4H), (m, 3H), 7.36 (m, 2H), 8.00 (d, 2H). (100 MHz, CDCl 3 ) δ 32.4, 116.1, 118.5, 120.0, 121.1, 124.4, 125.3, 129.4, 130.2, 130.4, 155.6, 156.1, 160.5, 168.0, calcd for C 21 H , found [MH] + CF 3 H
11 75b 19 F MR 75c 76c (400 MHz, DMS-d 6 ) δ 6.68 (m, 1H), (m, 4H), 7.24 (tt, J = 7.5, 1.2 Hz), 7.47 (m, 2H), 7.55 (t, J = 2.8 Hz, 1H), 7.63 (d, J = 8.5 Hz, 1H), 7.91 (dd J = 8.5, 1.7 Hz), 8.11 (d, J = 8.9 Hz), 8.46 (m, 1H), (s, 1H). (100 MHz, DMS-d 6 ) δ 102.7, 112.5, 114.2, 118.3, 119.7, 120.6, 121.2, 121.2, 124.5, 127.8, 129.2, 130.3, 138.4, 155.4, 159.7, 167.6, 170.9, calcd for C 22 H , found [MH] + H (400 MHz, CDCl 3 ) δ 6.71 (m, 1H), 7.13 (d, J = 8.7 Hz, 2H), 7.16 (d, J = 8.9 Hz, 2H), 7.32 (d, J = 8.7 Hz, 2H), 7.52 (d, J = 8.6 Hz, 1H), 7.63 (d, J = 8.9 Hz, 2H), 8.06 (d,d, J = 8.6, 1.61 Hz, 1H), 8.22 (d, J = 8.9 Hz, 2H), 8.52 (s, 1H), 8.57 (t, J = 0.8 Hz, 1H). (100 MHz, CDCl 3 ) δ 104.3, 119.9, 116.3, 118.9, 119.8, 122.2, 122.4, 123.5, (q, J CF = Hz), (q, J CF = 33.2 Hz), 126.2, (q, J CF = 3.8 Hz), 128.2, 129.7, 138.3, 158.5, 159.8, 168.3, (376 MHz, CDCl 3 ) δ (s, 3F). calcd for C 23 H 14 F , found [MH] + H (400 MHz, DMS-d 6 ) δ 6.68 (m, 1H), 7.15 (d, J =8.8 Hz, 2H), (m, 2H), (m, 2H), 7.55 (t, J = 2.8 Hz, 1H), 7.66 (d, J = 8.5 Hz, 1H), 7.91 (dd J = 8.5, 1.6 Hz), 8.10 (d, J = 8.8 Hz, 2H), 8.46 (m, 1H), (s, 1H). (100 MHz, DMS-d 6 ) δ 102.7, 112.5, 114.1, 116.8, 117.0, 117.9, 120.5, 121.1, 121.2, (d, J CF = 8.6 Hz), 127.8, 129.2, 138.4, 151.4, 160.0, 167.5, calcd for C 22 H 14 F , found [MH] + CF 3 F
12 77b (400 MHz, DMS-d 6 ) δ (m, 2H), (m, 2H), (m, 2H), 7.98 (s, 1H), (m, 2H), 8.23 (s, 1H), (s, 1H). (100 MHz, DMS-d 6 ) δ 116.8, 117.0, 117.8, 121.0, 121.8, 121.9, 122.8, 125.9, 129.2, 138.2, 151.3, 151.4, 157.7, 160.0, 167.3, calcd for C 17 H 12 F , found [MH] + 77c (400 MHz, DMS-d 6 ) δ (m, 4H), 7.81 (d, J = 8.8 Hz, 2H), 8.13 (d, J = 8.8 Hz, 2H), 8.78 (d, J = 2.4 Hz, 1H), 8.90 (d, J =2.4 Hz, 1H), (br s, 1H); (100 MHz, DMS-d 6 ) δ 101.3, 119.3, 119.8, 121.7, 124.2, 124.5, (q, J CF = 4.0 Hz), 129.5, 136.9, 138.0, 145.0, 154.1, 158.3, 159.1, 167.5, calcd for C 20 H 12 F , found [MH] + 78b (400 MHz, DMS-d 6 ) δ (m, 6H), (m, 2H), (m, 2H), (br s, 1H). (100 MHz, DMS-d 6 ) δ 101.9, 117.5, 117.7, 118.4, 121.0, 122.6, 122.7, 129.9, 137.5, 138.6, 145.6, 151.8, 151.9, 154.8, 158.3, 160.7, 161.0, 168.2, calcd for C 19 H 12 F , found [MH] + 78c (400 MHz, CDCl 3 ) δ (m, 4H), (m, 3H), (m, 1H), (m, 2H), 9.66 (br, 1H). (100 MHz, DMS-d 6 ) δ 109.8, 117.6, 120.0, 120.4, 122.4, 123.5, 124.9, 125.3, 126.1, 126.2, 128.3(q, J CF = 3.6 Hz), 130.1, 138.3, 159.0, 159.8, 168.1, calcd for C 19 H 11 F , found [MH] +
13 79a (400 MHz, CDCl 3 ) δ (m, 6H), (m, 1H), (m, 1H), (m, 2H), 9.66 (br, 1H). (100 MHz, DMS-d 6 ) δ 109.7, 117.4, 117.6(2C), 118.4, 121.1, 122.5, 122.6, 126.0, 129.8, 138.2, 151.8, 151.9, 158.3, 160.7, 160.9, 168.1, calcd for C 20 H 11 F 4 4 a , found [Ma] + 80a (600 MHz, CDCl 3 ) δ 4.12 (br s, 2H), (m, 2H), 5.36 (ddd, J = 10.9, 3.2, 1.8 Hz, 1H), 5.72 (ddd, J = 17.3, 3.5, 1.8 Hz, 1H), 6.12 (ddd, J = 17.3, 10.9, 4.7 Hz, 1H), 6.27 (d, J = 2.2 Hz, 1H), 6.37 (dd, J = 8.5, 2.2 Hz, 1H), (m, 4H), 7.17 (dt, J = 7.5, 1.2 Hz, 1H), (m, 2H), 8.00 (d, J = 8.5 Hz, 1H), 8.13 (d, J = 8.8 Hz, 2H). (150 MHz, CDCl 3 ) δ 69.4, 98.9, 104.1, 107.7, 117.6, 118.5, 119.9, 122.5, 124.2, 129.4, 130.1, 132.6, 133.4, 152.2, 156.5, 159.5, 159.9, 167.7, calcd for C 23 H 19 3 a , found [Ma] + 80b (600 MHz, acetone-d 6 ) δ (m, 2H), 7.15 (d, J = 9.0 Hz, 2H), 7.23 (tt, J = 7.4, 1.0 Hz, 1H), (m, 4H), 8.14 (d, J = 9.0 Hz, 2H), 8.29 (dd, J = 8.8, 5.3 Hz, 2H). (125 MHz, acetone-d 6 ) δ (d, J CF = 22.4 Hz), 119.2, 120.7, (d, J CF = 2.8 Hz), 122.4, 125.3, 130.1, 131.1, (d, J CF = 9.5 Hz), 157.0, 161.4, (d, J CF = Hz), 169.2, calcd for C 20 H 14 F , found [MH] + 81b Lit. 1
14 81c 83b (600 MHz, acetone-d 6 ) δ (m, 4H), 7.79 (d, J = 8.2 Hz, 2H), 7.86 (d, J = 8.2 Hz, 2H), 8.15 (d, J = 8.8 Hz, 2H), 8.20 (d, J = 8.8 Hz, 2H). (150 MHz, acetone-d 6 ) δ 120.1, 120.7, 123.7, 124.2, (q, J CF = 271.0), 126.0, 128.3, (q, J CF = 3.9 Hz), 130.4, 130.7, 133.6, 159.7, 160.7, 169.2, calcd for C 21 H 13 BrF , found [MH] + Br (400 MHz, CDCl 3 ) δ (m, 6H), 7.65 (d, J = 8.4 Hz, 2H), (m, 4H). (100 MHz, CDCl 3 ) δ 116.7, 116.9, 118.0, 121.5, 121.6, 121.7, 123.4, 127.9, 129.6, 129.8, 132.7, (2C), 158.4, 160.9, 168.7, calcd for C 20 H 12 BrF , found [MH] + F 85c (600 MHz, acetone-d 6 ) δ 2.15 (s, 3H, CH 3 ), (m, 4H, ArH), calcd for C 23 H 17 F , found [MH] + 86b (400 MHz, CDCl 3 ) δ 1.35 (t, J = 7.2 Hz, 6H), (m, 4H), (m, 6H), (m, 2H), (m, 2H), (m, 2H). (100 MHz, CDCl 3 ) δ 16.2, 16.3, 62.4, 62.5, 116.4, 116.7, 117.7, 121.1, 121.3, 121.4, 127.4, 127.8, 129.3, 132.2, 132.3, 132.4, 134.1, 151.6, 158.1, 160.5, 160.6, 168.5, calcd for C 24 H 23 F 2 5 P , found [MH] + (600 MHz, CDCl 3 ) δ 3.14 (s, 3H), 6.76 (s, 1H), 7.14 (d, J = 8.5 Hz, 2H), 7.16 (d, J = 8.8 Hz, 2H), 7.37 (d, J = 8.8 Hz, 2H), 7.64 (d, J = 8.5 Hz, 2H), 8.18 (d, J = 8.8 Hz, 2H), 8.22 (d, J = 8.8 Hz, 2H). calcd for C 22 H 17 F S , found [MH] +
15 87b 87c (400 MHz, DMS-d 6 ) δ (m, 4H), 7.66 (s, 2H), 7.82 (d, J = 9.2 Hz, 2H), 8.08 (d, J = 8.4 Hz, 2H), (m, 2H), 8.40 (d, J = 8.0 Hz, 2H). (100 MHz, DMS-d 6 ) δ 120.0, 120.5, 122.5, 124.9, 126.2, 126.7, 127.5, (q, J CF = 4.0 Hz), 129.5, 130.2, 148.6, 159.0, 159.8, 168.6, calcd for C 21 H 15 F S , found [MH] + 88c (400 MHz, CD 3 D) δ (m, 6H), (m, 4H), 8.35 (d, J = 6.8 Hz, 2H). (100 MHz, DMS-d 6 ) δ 116.9, 117.1, 117.9, 120.5, 122.0, 122.1, 126.1, 126.9, 128.8, 129.4, 147.9, 151.3, 151.3, 157.8, 160.2, 160.4, 168.0, calcd for C 20 H 15 F 3 4 S , found [MH] + 89c (500 MHz, DMS-d 6 ) δ 6.41 (s, 2H), 7.16 (d, J = 8.8 Hz, 2H), (m, 2H), (m, 2H), (m, 4H), 8.26 (d, J = 8.2 Hz, 2H). (125 MHz, DMS-d 6 ) δ (d, J CF = 23.9 Hz), 117.9, 120.5, (d, J CF = 8.2 Hz), 125.5, 127.9, 128.6, 129.3, 138.3, (d, J CF = 2.5 Hz), (d, J CF = 241.1), 160.3, 166.8, 167.9, calcd for C 21 H 15 F , found [MH] + 19 F MR (500 MHz, DMS-d 6 ) δ 7.15 (d, J = 9.0 Hz, 2H), 7.13 (dd, J = 8.9, 4.5 Hz, 2H), 7.31 (t, J = 8.9 Hz, 2H), 8.10 (d, J = 9.0 Hz, 2H), 8.18 (d, J = 8.8 Hz, 2H), 8.30 (d, J = 8.8 Hz, 2H). (125 MHz, DMS-d 6 ) δ 116.9, 117.9, 120.5, 121.9, 126.8, 128.2, 129.3, 130.3, 134.7, 151.2, 158.9, 160.3, 166.4, 167.9, (282 MHz, DMS-d 6 ): δ
16 calcd for C 21 H 12 F 2 a , found [MH] + 90c 19 F MR 91c (500 MHz, CDCl 3 ) δ 3.98 (s, 3H), (m, 6H), 8.14 (d, J = 9.0 Hz, 2H), 8.22 (d, J = 8.4 Hz, 2H), 8.29 (d, J = 8.4 Hz, 2H). (125 MHz, DMS-d 6 ) δ 52.5, 116.6, 117.8, 121.2, 121.4, 127.9, 128.1, 129.4, 130.2, 133.7, 151.7, 159.3, 160.6, 166.0, 168.6, (282 MHz, CDCl 3 ): δ calcd for C 22 H 16 F , found [MH] + 92c (400 MHz, CDCl 3 ) δ (m, 6H), (m, 1H), (m, 2H), (m, 1H), (m, 1H), (s, 1H). (100 ΜHz, DMS-d 6 ) δ 114.9, 117.4, 117.7, 118.5, 121.0, 121.2, 122.5, 122.6, 126.1, 129.9, 134.5, 138.0, 152.0, 156.4, 158.3, 160.7, 160.8, 168.4, calcd for C 20 H 13 F , found [MH] + 94a (400 MHz, DMS-d 6 ) δ 5.02 (br, 2H), 6.84 (d, J = 8.4 Hz, 1H), (m, 2H), (m, 2H), (m, 3H), 7.42 (d, J = 2.0 Hz, 1H), (m, 2H). (100 MHz, DMS-d 6 ) δ 113.3, 115.1(2C), 117.4, 117.7, 118.0, 118.5, 121.8, 122.5, 122.6, 129.8, 138.3, 149.5, (2C), 158.3, (2C), 168.1, calcd for C 20 H 15 F , found [MH] +
17 95a (600 MHz, DMS-d 6 ) δ 3.98 (s, 3H), 4.30 (s, 2H), 6.77 (d, J = 8.2 Hz, 1H), (m, 4H), 7.17 (tt, J = 7.5, 1.0 Hz, 1H), 7.39 (dd, J = 7.5, 1.0 Hz, 2H), 7.58 (d, J = 1.8 Hz, 1H), 7.70 (dd, J = 8.2, 1.8 Hz, 1H), 8.12 (d, J = 9.1 Hz, 2H). (150 MHz, DMS-d 6 ) δ 56.0, 109.8, 113.8, 114.0, 118.6, 119.8, 122.2, 122.8, 124.2, 129.5, 130.1, 141.2, 146.8, 156.4, 160.1, 168.4, calcd for C 21 H , found [MH] + 96a 97a H (400 MHz, DMS-d 6 ) δ 7.12 (m, 1H) (m, 4H), 7.25 (tt, J = 7.5, 1.1 Hz, 1H), (m, 3H), 7.56 (m, 1H), 7.62 (m, 1H), 8.09 (d, J = 8.9 Hz), (s, H). (100 MHz, DMS-d 6 ) δ 114.1, 118.3, 118.6, 119.8, 120.5, 120.8, 124.4, 124.6, 129.2, 130.4, 130.9, 155.4, 158.0, 160.0, 167.8, calcd for C 20 H , found [MH] + I H (400 MHz, DMS-d 6 ) δ (m, 4H), 7.25 (t, d, J = 7.3, 0.8 Hz, 1H), 7.38 (dd, J = 8.2, 1.9 Hz, 1H), 7.48 (t, J = 7.7 Hz, 2H), 7.64 (d, J = 1.9 Hz, 1H), 7.98 (td, J = 8.2 Hz, 1H), 8.08 (d, J = 8.8 Hz, 2H). (400 MHz, DMS-d 6 ) δ 91.8, 113.0, 118.3, 119.8, 119.9, 120.6, , 124.3, 124.6, 129.2, 130.4, 140.3, 159.9, calcd for C 20 H 13 I , found [MH] + (400 MHz, CDCl 3 ) δ 7.05 (m, 1H), (m, 4H), 7.15 (m, 1H), 7.20 (tt, J = 7.4, 1.1 Hz, 1H), (m, 2H), 7.53 (m, 1H), 8.00 (dd, J = 8.0, 1.7 Hz, 1H), 8.09 (d, J = 9.0 Hz), (s, 1H). (100 MHz, CDCl 3 ) δ 108.4, 118.0, 118.6, 120.2, 120.4, 122.5, 124.6, 128.1, 129.6, 130.3, 135.5, 156.1, 158.4, 160.9, 166.9, calcd for C 20 H , found [MH] + H
18 98a 99a (600 MHz, CDCl 3 ) δ 4.17 (s, 2H), (m, 2H), (m, 4H), 7.19 (t, J = 7.4 Hz, 1H), 7.40 (dd, J = 7.4, 1.2 Hz, 2H), 7.76 (d, J = 8.8 Hz, 1H), 8.06 (d, J = 8.8 Hz, 2H), (s, 1H). (150 MHz, CDCl 3 ) δ 99.3, 101.3, 108.1, 118.5, 120.0, 120.9, 124.5, 129.5, 129.7, 130.2, 153.2, 156.2, 160.3, 160.6, 166.4, calcd for C 20 H , found [MH] + 99b (500 MHz, CDCl3) δ 4.08 (s, 3H), (m, 2H), 7.10 (d, J = 9.0 Hz, 2H), 7.19 (tt, J = 7.5, 1.1 Hz, 1H), 7.27 (d, J = 8.8 Hz, 1H), 7.40 (dd, J = 7.4, 1.1 Hz, 2H), 8.12 (d, J = 9.0 Hz, 2H), 8.37 (dd, J = 8.8, 2.2 Hz, 1H), 8.71 (d, J = 2.2 Hz, 1H). (150 MHz, CDCl3) δ 57.2, 105.2, 114.3, 117.1, 118.5, 120.0, 121.2, 121.3, 124.5, 126.0, 129.5, 130.2, 133.7, 156.0, 160.6, 168.8, calcd for C 21 H , found [MH] + (400 MHz, CDCl 3 ) δ 4.09 (s, 3H), (m, 4H), (m, 1H), (m, 2H), (m, 2H), 8.38 (dd, J = 2.0 Hz, 1H), 8.72 (d, J = 2.4 Hz, 1H). 99c (100 MHz, CDCl 3 ) δ 57.2, 114.3, 117.0, 119.1, 119.7, 122.7, 122.9, 125.6, 126.0, 126.3, (q, J = 3.6 Hz), 129.8, 133.7, 140.2, 156.1, 159.0, 159.6, 168.7, calcd for C 22 H 15 F , found [MH] + (400 MHz, CDCl 3 ) δ 4.13 (s, 3H), (m, 5H), (m, 2H), (m, 2H), (m, 1H), 8.76 (d, J = 2.0 Hz, 1H). (100 MHz, CDCl 3 ) δ 57.2, 114.3, 116.7, 116.9, 117.1, 118.1, 121.4, 121.6, 121.7, 125.9, 129.6, 133.6, 140.2, 151.9, 152.0, 156.0, 158.4,
19 100a 160.8, 160.9, 168.8, calcd for C 21 H 14 F 3 a , found [Ma] + 101b (600 MHz, DMS-d 6 ) δ 3.88 (s, 3H), 7.02 (d, J = 8.5 Hz, 1H), (m, 4H), 7.24 (tt, J = 7.4, 1.1 Hz, 1H), (m, 1H), (m, 3H), 8.06 (d, 2H, J = 8.8 Hz). (150 MHz, DMS-d 6 ) δ 55.6, 110.6, 111.7, 115.8, 116.8, 118.2, 119.8, 121.1, 124.5, 129.1, 130.3, 138.6, 150.2, 155.4, 160.0, 167.5, calcd for C 21 H , found [MH] + 101c (400 MHz, CDCl 3 ) δ 3.99 (s, 3H), 4.03 (s, 3H), 7.02 (d, J = 8.8 Hz, 1H), (m, 4H), (m, 2H), 7.70 (d, J = 2.0 Hz, 1H), 7.85 (dd, J = 2.0 Hz, 1H), (m, 2H). (100 MHz, CDCl 3 ) δ 56.3, 56.4, 110.8, 111.4, 117.1, 118.9, 119.7, 122.3, 122.9, 123.3, 125.7, 125.8, 126.1, (q, J = 3.8 Hz), 129.7, 149.6, 153.2, 158.6, 159.7, 168.4, calcd for C 23 H 18 F , found [MH] + 102b (400 MHz, CDCl 3 ) δ 3.96 (s, 3H), 3.99 (s, 3H), 6.98 (d, J = 8.4 Hz, 1H), (m, 5H), 7.67 (d, J = 2.0 Hz, 1H), 7.82 (dd, J = 2.0 Hz, 1H), (m, 2H). (100 MHz, CDCl 3 ) δ 56.3, 56.4, 110.7, 111.3, 116.7, 116.9, 117.1, 118.1, 121.5, 121.6, 121.9, 122.3, 129.5, 149.5, 152.0, 152.1, 153.1, 158.3, 160.6, 160.7, 168.5, calcd for C 22 H 18 F , found [MH] + CF 3 H
20 102c 103b (400 MHz, CDCl 3 ) δ (m, 5H), 7.65 (d, J = 8.8, 2H), 8.04 (d, J = 2.4 Hz, 1H), (m, 2H). (100 MHz, CDCl 3 ) δ 107.5, 119.2, 119.7, 122.7, 126.0, 126.3, (q, J CF = 3.0 Hz), 129.8, 131.8, 137.6, 159.0, 159.5, 168.5, calcd for C 18 H 12 F , found [MH] + H (400 MHz, CD 3 D) δ (m, 7H), 7.90 (s, 1H), (m, 2H). (100 MHz, DMS-d 6 ) δ 106.8, 116.8, 117.0, 117.8, 120.7, 121.9, 122.0, 129.2, 131.1, 136.8, 151.3, 157.6, 160.0, 160.2, 167.5, calcd for C 17 H 12 F , found [MH] + F 104b (400 MHz, DMS-d 6 ) δ 4.37 (d, J = 6.0 Hz, 2H), 5.38 (t, J = 6.0 Hz, 1H), (m, 4H), 7.81 (d, J = 8.4 Hz, 2H), 8.16 (d, J =8.4 Hz, 2H), 8.37 (s, 1H). (100 MHz, DMS-d 6 ) δ 49.6, 73.9, 93.7, 103.5, 119.3, 119.8, 122.1, 124.2, 124.5, (q, J CF = 3.5 Hz), 129.5, 134.6, , 159.2, 167.4, calcd for C 21 H 14 F , found [MH] + (400 MHz, CDCl 3 ) δ (m, 3H), (m, 2H), (m, 2H), 3.20 (t, J = 8.0 Hz, 2H), 4.81 (br s, 1H), (m, 4H), 7.43 (s, 1H), 7.64 (d, J =8.0 Hz, 2H), (m, 2H). (100 MHz, CDCl 3 ) δ 14.1, 20.5, 31.9, 46.6, 119.1, 119.2, 119.6, 122.9, 125.9, 126.2, (q, J CF = 3.6 Hz), 129.8, 136.9, 158.8, 159.5, 159.6, 167.6, calcd for C 22 H 21 F , found [MH] +
21 105b 106b (400 MHz, CDCl 3 ) δ 1.02 (t, J = 7.2 Hz, 3H), 1.29 (d, J = 6.4 Hz, 4H), (m, 2H), (m, 1H), (m, 4H), 7.45 (s, 1H), 7.64 (d, J = 8.4 Hz, 2H), (m, 2H). (100 MHz, CDCl 3 ) δ 10.4, 20.5, 29.8, 53.5, 116.3, 119.1, 119.7, 122.5, 122.9, 125.6, 125.9, 126.2, (q, J CF = 3.6 Hz), 129.8, 135.9, 158.9, 159.5, 167.6, calcd for C 22 H 21 F , found [MH] + 107b (400 MHz, CDCl 3 ) δ (m, 5H), (m, 3H), 2.10 (d, J = 10.4 Hz, 2H), 3.18 (br s, 1H), 4.90 (d, J = 3.2 Hz, 1H), (m, 3H), 7.37 (s, 1H), (m, 2H), (m, 2H). (150 MHz, CDCl 3 ) δ 24.8, 26.1, 33.4, 54.9, 115.9, 119.1, 119.6, 122.9, 125.6, 125.9, 126.2, (q, J CF = 3.6 Hz), 129.7, 135.6, 158.9, 159.5, 167.6, calcd for C 24 H 23 F , found [MH] + 110b (400 MHz, CDCl 3 ) δ (m, 4H), (m, 2H), (m, 2H), (m, 1H), (m, 1H), (m, 3H), 7.36 (d, J = 1.2 Hz, 1H), 7.64 (d, J = 8.8 Hz, 2H), (m, 2H). (100 MHz, CDCl 3 ) δ 24.3, 33.7, 57.7, 116.4, 119.1, 119.6, 122.8, 125.6, 125.9, 126.2, (q, J CF = 3.7 Hz), 129.8, 136.2, 158.9, 159.5, 167.6, calcd for C 23 H 21 F , found [MH] +
22 111b (400 MHz, CDCl 3 ) δ (m, 2H), 1.47 (s, 9H), (m, 2H), (m, 2H), (m, 1H), 4.03 (br, 2H), (m, 4H), 7.40 (s, 1H), (m, 2H), (m, 2H). (100 MHz, CDCl 3 ) δ 28.7, 32.4, 53.2, 80.0, 119.1, 119.2, 119.6, 122.6, 122.7, 122.9, 125.6, 126.0, 126.4, (q, J = 4.4 Hz), 129.7, 134.9, 155.0, 159.0, 159.5, 167.6, calcd for C 28 H 30 F , found [MH] + 112a 113b (400 MHz, CDCl 3 ) δ (m, 6H), (m, 4H), (m, 4H), 7.60 (d, J = 8.4, 2H), (m, 3H). (100 MHz, CDCl 3 ) δ 16.5, 16.6, 63.2, 63.3, 108.1, 110.3, 119.2, 119.7, 122.5, 122.9, 125.6, 126.0, 126.3, (q, J CF = 3.6 Hz), 129.8, 138.8, 139.0, 159.0, 159.5, 168.4, calcd for C 22 H 21 F P , found [MH] + H (400 MHz, DMS-d 6 ) δ (m, 4H), 7.25 (tt, J = 7.4, 1.1 Hz, 1H), (m, 2H), 7.82 (d, J = 8.8 Hz, 2H), (s, 1H). (100 MHz, DMS-d 6 ) δ 117.7, 118.2, 119.8, 124.7, 128.2, 130.4, 155.1, 156.9, 160.0, calcd for C 14 H , found [MH] + (600 MHz, acetone-d 6 ) δ 2.66 (s, 3H), 7.25 (d, J = 8.8 Hz, 2H), 7.27 (d, J = 8.5 Hz, 2H), 7.78 (d, J = 8.5 Hz, 2H), 8.11 (d, J = 8.8 Hz, 2H). (150 MHz, acetone-d 6 ) δ 12.3, 120.0, 120.7, 124.1, (q, J CF = Hz), (q, J CF = 32.5 Hz), (q, J CF = 3.7 Hz), 130.2, 159.4, (q, J CF = 1.5 Hz), 168.5, calcd for C 16 H 12 F , found [MH] +
23 114a 115a 116b (400 MHz, CDCl 3 ) δ (m, 4H), 7.20 (t, J = 7.5 Hz, 1H), (m, 2H), 8.06 (d, J = 6.1 Hz, 2H), 8.13 (m, 2H), 8.89 (d, J = 6.1 Hz, 2H). (100 MHz, CDCl 3 ) δ 118.6, 120.1, 121.0, 121.7, 124.5, 129.6, 130.2, 148.8, (2C), 156.1, 160.8, calcd for C 19 H , found [MH] + (400 MHz, DMS-d 6 ) δ (m, 5H), (m, 2H), (m, 4H), 8.43 (m, 2H). (100 MHz, DMS-d 6 ) δ 118.3, 119.8, 120.3, 124.5, 125.2, 129.2, 130.3, 140.0, 151.1, 155.2, 160.0, 168.0, calcd for C 19 H , found [MH] + 117b (400 MHz, DMS-d 6 ) δ 7.09 (d, J = 7.2 Hz, 4H), 7.54 (d, J = 7.2 Hz, 2H), 7.71 (d, J = 6.8 Hz, 2H), 8.77 (s, 1H). (100 MHz, DMS-d 6 ) δ 117.8, 120.6, 120.7, 121.5, 123.4, 123.6, 123.9, 126.1, (q, J CF = 3.1 Hz), 137.4, 149.7, 153.3, calcd for C 17 H 11 F , found [MH] + 119c (400 MHz, DMS-d 6 ) δ (m, 4H), 7.81 (d, J = 8.8 Hz. 2H), (m, 2H), 8.99 (d, J = 7.2, 1H). (100 MHz, DMS-d 6 ) δ 120.0, 120.4, 122.5, 124.9, 125.2, 126.2, (q, J CF = 3.6), 130.1, 159.0, 159.8, 159.8, 168.2, calcd for C 11 H 11 F , found [MH] +
24 120b (400 MHz, CDCl 3 ) δ 1.37 (s, 3H), 1.39 (s, 3H), (m, 1H), 6.82 (s, 1H), (m, 5H), (m, 2H), (br s, 1H). (100 MHz, DMS-d 6 ) δ 103.7, 116.7, 116.9, 117.9, 121.4, 121.6, 121.7, 129.5, 151.8, 151.9, 153.1, 158.3, 160.6, 160.7, 168.3, calcd for C 20 H 18 F , found [MH] + 120c (400 MHz, DMS-d 6 ) δ 6.54 (d, J = 9.6 Hz, 1H), (m, 4H), 7.80 (d, J = 8.4 Hz, 2H), (m, 1H), (m, 2H), 8.35 (d, J = 2.8 Hz, 1H), (s, 1H). (100 MHz, DMS-d 6 ) δ 102.6, 119.2, 119.8, 120.7, 122.1, 124.1, 124.5, (q, J CF = 4.0 Hz), 129.4, 138.0, 139.4, 158.1, 159.2, 162.0, 167.3, calcd for C 20 H 13 F , found [MH] + 121b (400 MHz, DMS-d 6 ) δ (m, 1H), (m, 2H), (m, 2H), (m, 2H), (m, 3H), 8.34 (d, J = 2.0 Hz, 1H), (s, 1H). (100 MHz, DMS-d 6 ) δ 102.6, 116.8, 117.0, 117.8, 120.7, 121.8, 121.9, 129.2, 138.0, 139.3, 151.2, 151.3, 157.6, 160.0, 160.1, 162.0, 167.4, calcd for C 19 H 13 F , found [MH] + (400 MHz, DMS-d 6 ) δ 5.56 (s, 2H), 7.02 (d, J = 2.4 Hz, 1H), (m, 4H), 7.64 (d, J = 1.6 Hz, 1H), 7.80 (d, J = 8.4 Hz, 2H), (m, 2H), (s, 1H). (100 MHz, DMS-d 6 ) δ 104.7, 106.3, 119.9, 120.4, 123.0,123.5, 124.5, 124.8, 125.2, 126.2, 128.3(q, J CF = 3.8 Hz), 130.0, 139.9, 158.5, 158.8, 159.9, 167.9, calcd for C 20 H 14 F , found [MH] +
25 121c 122b (400 MHz, DMS-d 6 ) δ 5.55 (s, 2H), 7.01 (d, J = 2.4 Hz, 1H), (m, 2H), (m, 2H), (m, 2H), 7.62 (d, J = 2.0 Hz, 1H), (m, 2H). (100 MHz, DMS-d 6 ) δ 104.0, 105.6, 116.8, 117.0, 117.8, 120.6, 121.8, 121.9, 139.2, 151.2, 151.3, 157.6, 157.8, 160.0, 160.1, 167.3, calcd for C 19 H 14 F , found [MH] + 122c (400 MHz, CDCl 3 ) δ 4.01 (br, 2H), (m, 4H), (m, 2H), (m, 1H), (m, 2H), 8.31 (d, J = 2.4 Hz, 1H), 8.83 (d, J = 1.6 Hz, 1H). (100 MHz, CDCl 3 ) δ 119.1, 119.7, 120.8, 122.7, 125.6, 125.9, (q, J CF = 3.0 Hz), 129.8, 139.1, 141.1, 142.8, 158.9, 159.5, 168.5, calcd for C 20 H 14 F , found [MH] + 123b (400 MHz, CDCl 3 ) δ 3.99 (br, 2H), (m, 6H), (m, 1H), (m, 2H), 8.30 (d, J = 2.4 Hz, 1H), 8.82 (d, J = 1.6 Hz, 1H). (100 MHz, DMS-d 6 ) δ 116.7, 117.0, 118.0, 119.7, 120.9, 121.4, 121.6, 121.7, 129.6, 139.2, 141.1, 142.8, 151.9, 160.8, 160.9, 168.7, calcd for C 19 H 14 F , found [MH] + (400 MHz, DMS-d 6 ) δ (m, 4H), (m, 1H), (m, 1H), (m, 3H), (m, 2H), 8.34 (d, J = 8.4 Hz, 1H). (100 MHz, DMS-d 6 ) δ 111.4, 119.1, 119.9, 120.5, 121.4, 122.2, 123.4, 124.1, 124.4, 127.4, (q, J CF = 3.6 Hz), 129.5, 129.8, 141.0, 158.1, 159.2, 159.3, 167.4, calcd for C 22 H 14 F , found [MH] +
26 123c 124a 125b (400 MHz, DMS-d 6 ) δ (m, 4H), (m, 2H), (m, 1H), (m, 1H), 7.77 (d, J = 8.4 Hz, 1H), (m, 2H), 8.33 (d, J = 8.4 Hz, 1H). (100 MHz, DMS-d 6 ) δ 111.4, 116.8, 117.0, 117.9, 120.5, 120.8, 121.4, 121.7, 121.8, 123.4, 127.4, 129.3, 129.9, 141.0, 151.3, 151.4, 157.6, 160.0, 160.1, 167.5, calcd for C 21 H 14 F , found [MH] + H (400 MHz, CDCl 3 ) δ (m, 4H), 7.19 (tt, J = 7.4, 1.1 Hz, 1H), 7.40 (dd, J = 8.6, 8.4 Hz, 2H), 7.66 (d, J = 8.8 Hz, 1H), 8.16 (d, J = 8.8 Hz, 2H), (m, 2H), 8.72 (s, 1H). (100 MHz, CDCl 3 ) δ 110.8, 118.0, 118.6, 120.0, 121.8, 122.9, 123.6, 124.4, 126.7, 129.5, 130.2, 136.7, 141.7, 156.4, 160.4, 168.7, calcd for C 21 H , found [Ma] + 125c (400 MHz, CDCl 3 ) δ (m, 4H), (m, 1H), 7.65 (d, J = 8.4 Hz, 2H), (m, 2H), 8.35 (s, 1H), (m, 1H), (m, 1H). (100 MHz, DMS-d 6 ) δ 98.7, 116.9, 118.1, 119.1, 119.9, 122.6, 124.0, 124.4, (q, J CF = 3.0 Hz), 128.7, 129.4, 131.4, 144.7, 148.8, 157.9, 159.4, 167.1, calcd for C 22 H 14 F , found [MH] +
27 126c (400 MHz, DMS-d 6 ) δ (m, 2H), (m, 2H), (m, 2H), (m, 1H), 8.11 (d, J = 2.4 Hz, 1H), 8.14 (s, 1H), (m, 1H), 8.55 (d, J = 8.0 Hz, 1H), 8.60 (d, J = 2.4 Hz, 1H), (s, 1H). (100 MHz, DMS-d 6 ) δ 98.7, 116.7, 116.8, 117.0, 117.9, 118.0, 121.2, 121.7, 121.8, 128.6, 129.2, 131.3, 144.7, 148.8, (2C), 157.6, 159.9, 160.0, 167.2, calcd for C 21 H 14 F , found [MH] + 127c (400 MHz, CDCl 3 ) δ 3.21 (br s, 2H), 6.61 (s, 1H), 6.69 (s, 1H), (m, 6H), (m, 2H), 9.01(s, 1H). (100 MHz, CDCl 3 ) δ 106.1, 111.1, 115.6, 116.7, 116.9, 118.0, 121.5, 121.6, 121.7, 129.3, 129.4, 133.8, 151.9, 158.4, 160.6, 160.7, 167.8, calcd for C 18 H 14 F , found [MH] + 128a (400 MHz, CDCl 3 ) δ (m, 1H), (m, 7H), (m, 2H), 9.34 (br s, 1H). (100 MHz, CDCl 3 ) δ 111.6, 114.9, 116.7, 116.9, 117.3, 118.0, 121.5, 121.6, 121.7, 123.8, 129.5, 151.9, 152.0, 158.3, 160.6, 160.7, 167.9, calcd for C 18 H 13 F , found [MH] + ClH H (400 MHz, DMS-d 6 ) δ (m, 4H), (m, 4H), 3.51 (m, 1H), (m, 4H), 7.24 (tt, J = 7.4, 1.1 Hz), 7.47 (m, 2H), 8.01 (d, J = 8.9 Hz), 9.06 (m, 2H). (100 MHz, DMS-d 6 ) δ 25.55, 31.19, 41.97, , , , , , , , , , calcd for C 19 H , found [MH] +
28 131a 132a 133b (400 MHz, CDCl 3 ) δ (m, 4H), 3.25 (m, 1H), 3.58 (m, 2H), 4.07 (m, 2H), (m, 4H), 7.18 (tt, J = 7.4, 1.1 Hz, 1H), 7.39 (m, 2H), 8.04 (d, J = 8.9 Hz, 2H). (100 MHz, CDCl 3 ) δ 29.6, 33.8, 67.1, 118.6, 119.9, 121.6, 124.4, 129.4, 130.2, 156.3, 160.3, 168.0, calcd for C 19 H , found [MH] + (400 MHz, DMS-d 6 ) δ 2.22 (s, 2H), 2.44 (s, 1H), 2.58 (s, 1H), 3.65 (m, 2H), 5.18, (s, 1H), (m, 4H), 7.17 (t, J = 7.5 Hz, 1H), 7.37 (t, J = 7.8 Hz, 2H), 8.00 (d, J = 8.3 Hz, 2H), (s, 1H), (s, 1H). (100 MHz, DMS-d 6 ) δ 23.7, 30.1, 46.1, 54.0, 118.5, 120.0, 120.4, 124.5, 129.7, 130.2, 156.1, 160.7, 168.2, calcd for C 18 H , found [MH] + H HCl 134b (500 MHz, CDCl 3 ) δ (m, 2H), (m, 1H), (m, 1H), (m, 1H), 6.83 (s, 1H), 7.12 (d, J = 8.5 Hz, 4H), 7.62 (d, J = 8.5 Hz, 2H), 8.07 (d, J = 8.5 Hz, 2H). (125 MHz, CDCl 3 ) δ 26.4, 29.1, 50.4, 119.1, 119.7, 122.2, 126.0, 126.3, (q, J CF = 3.6 Hz), 129.8, 159.1, 159.4, 168.1, 178.0, b (500 MHz, CDCl 3 ) δ (m, 2H), (m, 1H), (m, 1H), (m, 1H), 7.11 (d, J = 8.5 Hz, 4H), 7.62 (d, J = 8.5 Hz, 2H), 8.06 (d, J = 8.5 Hz, 2H). (125 MHz, CDCl 3 ) δ 26.4, 29.2, 50.5, 119.1, 119.7, 122.3, 125.3, 126.0, 126.3, (q, J CF = 3.5 Hz), 129.8, 159.1, 159.4, 168.1, 178.3,
29 136a (400 MHz, DMS-d 6 ) δ 6.40 (d, J = 1.6 Hz, 1H), (m, 4H), 7.81 (d, J = 8.8 Hz, 2H), (m, 2H), (s, 1H), (s, 1H). calcd for C 19 H 11 F , found [MH] + 137a ClH H 2 (400 MHz, DMS-d 6 ) δ (m, 1H), (m, 1H), (m, 1H), (m, 4H), (m, 6H), 7.47 (t, J = 8.3 Hz, 2H), 7.99 (d, J = 8.6 Hz, 2H), 9.34 (s, 3H). (100 MHz, DMS-d 6 ) δ 37.3, 48.0, 118.3, 119.9, 124.6, 127.4, 128.6, 129.2, 129.3, 130.3, 134.2, 155.1, 160.1, 167.1, calcd for C 22 H , found [MH] + (600 MHz, DMS-d 6 ) δ 1.49 (quint, J = 7.4 Hz, 2H), 1.81 (quint, J = 7.4 Hz, 2H), 2.63 (t, J = 7.4 Hz, 2H), 3.00 (t, J = 7.4 Hz, 2H), (m, 4H), 7.24 (t, J = 7.4 Hz, 1H), 7.46 (t, J = 7.4 Hz, 2H), 8.00 (d, J = 8.8 Hz, 2H). (150 MHz, DMS-d 6 ) δ 23.3, 25.6, 30.5, 40.1, 118.3, 119.7, 120.9, 124.5, 129.1, 130.3, 155.3, 159.7, 167.0, calcd for C 18 H , found [MH] + Table S2. Minimal-Inhibitory concentrations (MICs) Compound umber E. faecium CTC 7171 S. aureus ATCC MIC (µg/ml) MIC (µg/ml) 57a b c a 2 4
30 58b c >128 >128 59b a > c b a b > a b a b c a b c a > b > b > b > b b c a 4 4
31 70b c b c a >32 >128 72b a b a a b c b c 128 >128 77b c b c 128 >128 79a > a - >128 80b - >128 81b - >128 81c >128 >128 82a >32 >32
32 82b - >128 83b c 32 >128 85c >128 >128 86b 32 >128 87b 128 >128 87c >128 >128 88c 64 >128 89c 128 >128 90c >128 >128 91c >128 >128 92c 128 >128 93b >128 >128 94a >128 >128 95a >128 >128 96a 32 >128 97a >128 >128 98a >128 >128 99a 128 >128 99b >128 >128 99c >128 > a >128 > b >128 > c >128 >128
33 102b 64 > c 32 > b >128 > b >128 > b 128 > b 128 > b >128 > b 16 > b >128 > b >128 > b >128 > a >128 > a - > a 64 > a 64 > b >128 > b > c >128 > c 64 > b 32 > c 64 > b 64 > c 128 > b >128 >128
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