All the reagents were procured from Hyclone Inc (Logan, UT, USA) and Aladdin (Shanghai, China), and they were used without prior purification. The separation and purification of all the reactions were conducted using silica gel column chromatography with a particle size of 300–400 mesh, and the progress was monitored by TLC plates coated with silica gel GF254. The 1H and 13C nuclear magnetic resonance (NMR) spectra were recorded on an Avance DRX400 spectrometer from Bruker (Beijing, China), operating at 600 MHz and 150 MHz, respectively. The reported chemical shift values are presented in terms of the chemical shift (δ) in parts per million (ppm). Mass spectrometry was performed on an Esquire 6000 mass spectrometer from Skyray Instrument Co., Ltd. (Jiangsu, China).
3.1.2. General Procedure to Prepare Compounds 1a–h, 2a–h, 3a–h, and 4a–h
Intermediates 1, 2, 3, and 4 (100 mg, 0.2 mmol) were dissolved in 10 mL of DMF, and EDCI (0.2 mmol, 0.5 eq.), HOBt (0.1 mmol), and pyridine (py, 0.1 mmol) were added sequentially. The mixture was stirred at room temperature for 30 min, followed by the addition of an amine substituent (0.3 mmol, 1.2 eq.). The reaction was continued under nitrogen protection at room temperature with stirring for 12 to 48 h. After the completion of the reaction was confirmed by thin-layer chromatography (TLC), the mixture was extracted with water and ethyl acetate, and the aqueous layer was dewatered using saturated sodium chloride. The organic layer was dried with anhydrous sodium sulfate and the solvent was concentrated under reduced pressure. The target compounds 1a–h, 2a–h, 3a–h, and 4a–h were obtained through purification by silica gel column chromatography using a dichloromethane-methanol solvent system at a ratio of 100:1 (v/v).
White solid (86%). 1H NMR (600 MHz, CDCl3) δ 8.78 (s, 1H, S-CH), 6.63 (d, J = 12.4 Hz, 1H, H-3′), 6.43 (d, J = 8.5 Hz, 1H, H-7), 6.36 (d, J = 12.4 Hz, 1H, H-2′), 6.12 (d, J = 8.5 Hz, 1H, H-6), 5.15–5.13 (m, 1H), 5.09–5.04 (m, 2H), 2.11–2.08 (m, 1H), 1.95 (d, J = 13.8 Hz, 4H), 1.89–1.87 (m, 1H), 1.78 (d, J = 6.7 Hz, 1H), 1.68 (d, J = 7.4 Hz, 1H), 1.64–1.61 (m, 1H), 1.51 (s, 2H), 1.45–1.42 (m, 2H), 1.40 (d, J = 6.5 Hz, 1H), 1.34–1.32 (m, 1H), 1.29 (s, 1H), 1.18 (s, 4H), 0.93 (d, J = 6.5 Hz, 3H, H-18), 0.84 (d, J = 6.8 Hz, 3H, H-28), 0.78 (s, 3H, H-21), 0.76–0.74 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 163.88, 161.15, 158.59, 146.81, 134.16, 133.85, 131.30, 131.00, 130.15, 130.02, 80.60, 78.39, 70.52, 55.13, 50.52, 49.90, 43.52, 41.75, 38.71, 38.24, 35.90, 33.13, 32.04, 31.81, 27.61, 24.88, 22.33, 19.86, 19.59, 18.94, 18.62, 16.99, 16.56, 11.86; HRMS (ESI) m/z: calcd for C34H47N3O5S [M + Na]+: 632.3236, found: 632.3125.
White solid (81%). 1H NMR (600 MHz, CDCl3) δ 7.48 (s, 1H, N-CH), 7.01 (d, J = 3.5 Hz, 1H, S-CH), 6.55 (d, J = 12.8 Hz, 1H, H-3′), 6.50 (d, J = 8.5 Hz, 1H, H-7), 6.30 (d, J = 12.8 Hz, 1H, H-2′), 6.17 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.6 Hz, 1H), 5.14 (dd, J = 15.1, 8.4 Hz, 2H), 2.13 (dd, J = 13.6, 5.3 Hz, 1H), 2.00 (d, J = 9.1 Hz, 4H), 1.94 (s, 1H), 1.86–1.83 (m, 1H), 1.74 (d, J = 9.1 Hz, 1H), 1.69 (d, J = 10.5 Hz, 1H), 1.59–1.55 (m, 2H), 1.49 (t, J = 5.3 Hz, 2H), 1.45 (d, J = 6.5 Hz, 1H), 1.40–1.37 (m, 1H), 1.35 (d, J = 7.3 Hz, 1H), 1.25 (s, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.91 (d, J = 6.8 Hz, 3H, H-28), 0.84–0.80 (m, 12H, H-21, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 164.90, 161.69, 158.40, 137.60, 135.73, 135.20, 134.82, 132.34, 131.07, 128.20, 113.94, 81.58, 79.43, 71.83, 56.17, 51.54, 50.91, 44.55, 42.79, 39.75, 39.26, 36.92, 34.11, 33.07, 32.80, 28.64, 25.90, 23.36, 20.89, 20.62, 19.97, 19.65, 17.97, 17.59, 12.88; HRMS (ESI) m/z: calcd for C35H48N2O5S [M + Na]+: 631.3284, found: 631.3183.
Yellow solid (79%). 1H NMR (600 MHz, CDCl3) δ 7.73 (dd, J = 8.7, 5.1 Hz, 1H, H-Ar), 7.53 (d, J = 9.5 Hz, 1H, H-Ar), 7.08 (t, J = 7.6 Hz, 1H, H-Ar), 6.52 (d, J = 13.1 Hz, 2H, H-3′, H-7), 6.36 (d, J = 13.2 Hz, 1H, H-2′), 6.21 (d, J = 8.4 Hz, 1H, H-6), 5.22 (dd, J = 15.1, 7.8 Hz, 2H), 5.17–5.13 (m, 1H), 2.21 (dd, J = 13.6, 5.0 Hz, 1H), 2.10–2.01 (m, 4H), 1.96 (d, J = 10.0 Hz, 1H), 1.85 (d, J = 6.8 Hz, 1H), 1.75 (s, 1H), 1.62 (s, 1H), 1.61–1.56 (m, 2H), 1.51 (d, J = 11.9 Hz, 2H), 1.48–1.45 (m, 1H), 1.41–1.38 (m, 1H), 1.35 (d, J = 8.4 Hz, 1H), 1.25 (s, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.91 (d, J = 6.7 Hz, 3H, H-28), 0.88 (s, 3H, H-21), 0.82 (d, J = 10.1 Hz, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 165.54, 162.84, 161.70, 159.63, 136.46, 135.19, 134.73, 132.36, 131.17, 128.81, 127.62, 122.09, 112.63, 107.80, 107.64, 81.60, 79.47, 72.48, 56.18, 51.54, 50.92, 44.57, 42.80, 39.75, 39.27, 36.95, 34.16, 33.08, 32.86, 28.65, 26.02, 23.38, 20.90, 20.63, 19.98, 19.65, 18.01, 17.60, 12.90; HRMS (ESI) m/z: calcd for C39H49FN2O5S [M + Na]+: 699.3346, found: 699.3239.
Yellow solid (77%). 1H NMR (600 MHz, CDCl3) δ 7.79 (dd, J = 8.9, 4.7 Hz, 1H, H-Ar), 7.50 (dd, J = 8.0, 2.6 Hz, 1H, H-Ar), 7.17 (td, J = 8.9, 2.6 Hz, 1H, H-Ar), 6.54–6.50 (m, 2H, H-3′, H-7), 6.35 (d, J = 13.2 Hz, 1H, H-2′), 6.20 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.6 Hz, 2H), 5.15 (dd, J = 15.3, 8.4 Hz, 1H), 2.23–2.19 (m, 1H), 2.09–2.01 (m, 4H), 1.96 (d, J = 10.5 Hz, 1H), 1.85 (d, J = 6.7 Hz, 1H), 1.74 (d, J = 3.7 Hz, 1H), 1.64 (d, J = 8.9 Hz, 1H), 1.60–1.55 (m, 2H), 1.50 (d, J = 11.4 Hz, 2H), 1.48–1.45 (m, 1H), 1.40–1.38 (m, 1H), 1.36 (d, J = 10.4 Hz, 1H), 1.25 (s, 4H), 1.00 (d, J = 6.7 Hz, 3H, H-18), 0.91 (d, J = 6.8 Hz, 3H, H-28), 0.88 (s, 3H, H-21), 0.84–0.81 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 165.57, 161.70, 158.91, 157.18, 145.20, 136.61, 135.19, 134.73, 133.27, 132.36, 131.16, 128.70, 122.25, 114.63, 107.66, 81.61, 79.47, 72.45, 56.18, 51.54, 50.92, 44.57, 42.79, 39.75, 39.27, 36.95, 34.16, 33.07, 32.86, 28.65, 26.01, 23.38, 20.90, 20.63, 19.98, 19.65, 18.01, 17.60, 12.89; HRMS (ESI) m/z: calcd for C39H49FN2O5S [M + Na]+: 699.3346, found: 699.3235.
White solid (77%). 1H NMR (600 MHz, CDCl3) δ 10.92 (s, 1H, H-N), 7.66 (d, J = 7.7 Hz, 2H, H-Ar), 7.34 (d, J = 7.7 Hz, 2H, H-Ar), 7.12 (d, J = 7.2 Hz, 1H, H-Ar), 6.52 (d, J = 8.5 Hz, 1H, H-7), 6.42 (d, J = 13.2 Hz, 1H, H-3′), 6.21 (d, J = 8.3 Hz, 1H, H-6), 6.15 (d, J = 13.3 Hz, 1H, H-2′), 5.22 (dd, J = 15.2, 7.6 Hz, 1H), 5.17–5.11 (m, 2H), 2.22 (dd, J = 13.6, 5.3 Hz, 1H), 2.06–2.00 (m, 4H), 1.97–1.95 (m, 1H), 1.85 (d, J = 6.6 Hz, 1H), 1.74 (d, J = 3.7 Hz, 1H), 1.64 (d, J = 3.9 Hz, 1H), 1.60–1.56 (m, 2H), 1.53–1.49 (m, 2H), 1.48–1.45 (m, 1H), 1.41–1.38 (m, 1H), 1.36 (d, J = 10.6 Hz, 1H), 1.25 (s, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.91 (d, J = 6.8 Hz, 3H, H-28), 0.88 (s, 3H, H-21), 0.84–0.81 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 165.96, 161.68, 140.41, 137.91, 135.18, 134.83, 132.36, 131.09, 129.02, 125.45, 124.64, 124.56, 120.14, 120.02, 81.72, 79.53, 71.68, 56.20, 51.59, 51.03, 44.58, 42.79, 39.74, 39.28, 36.96, 34.27, 33.07, 32.91, 28.65, 26.06, 23.39, 20.89, 20.61, 19.98, 19.66, 18.03, 17.60, 12.90; HRMS (ESI) m/z: calcd for C38H51NO5 [M + Na]+: 624.3767, found: 624.3665.
White solid (80%). 1H NMR (600 MHz, CDCl3) δ 11.10 (s, 1H, H-N), 7.63 (dd, J = 8.9, 4.8 Hz, 2H, H-Ar), 7.02 (t, J = 8.6 Hz, 2H, H-Ar), 6.53 (d, J = 8.5 Hz, 1H, H-7), 6.41 (d, J = 13.5 Hz, 1H, H-3′), 6.22 (d, J = 8.5 Hz, 1H, H-6), 6.16 (d, J = 13.4 Hz, 1H, H-2′), 5.22 (dd, J = 15.3, 7.7 Hz, 1H), 5.17–5.11 (m, 2H), 2.23 (dd, J = 13.6, 7.1 Hz, 1H), 2.08–1.99 (m, 4H), 1.95 (s, 1H), 1.85 (d, J = 6.6 Hz, 1H), 1.77–1.75 (m, 1H), 1.66 (d, J = 13.9 Hz, 1H), 1.61–1.55 (m, 2H), 1.52 (t, J = 5.4 Hz, 2H), 1.49–1.45 (m, 1H), 1.41–1.38 (m, 1H), 1.36 (d, J = 12.7 Hz, 1H), 1.25 (d, J = 9.7 Hz, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.92–0.89 (m, 6H, H-28, H-21), 0.84–0.81 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 166.11, 161.47, 160.30, 158.69, 140.57, 135.17, 134.77, 134.00, 132.37, 131.15, 125.53, 121.68, 121.63, 115.72, 115.57, 81.72, 79.56, 71.81, 56.20, 51.59, 51.03, 44.59, 42.79, 39.73, 39.27, 36.97, 34.27, 33.07, 32.91, 28.65, 26.07, 23.39, 20.89, 20.61, 19.97, 19.65, 18.04, 17.59, 12.89; HRMS (ESI) m/z: calcd for C38H50FNO5 [M + Na]+: 642.3673, found: 642.3572.
White solid (85%). 1H NMR (600 MHz, CDCl3) δ 10.90 (s, 1H, H-N), 7.58 (d, J = 9.0 Hz, 2H, H-Ar), 6.87 (d, J = 8.9 Hz, 2H, H-Ar), 6.52 (d, J = 8.5 Hz, 1H, H-7), 6.42 (d, J = 13.4 Hz, 1H, H-3′), 6.22 (d, J = 8.5 Hz, 1H, H-6), 6.14 (d, J = 13.4 Hz, 1H, H-2′), 5.24–5.20 (m, 1H), 5.16–5.11 (m, 2H), 3.80 (s, 3H, H-OCH3), 2.22 (d, J = 9.4 Hz, 1H), 2.07–2.01 (m, 4H), 1.95 (s, 1H), 1.85 (d, J = 6.5 Hz, 1H), 1.75 (d, J = 6.7 Hz, 1H), 1.65 (s, 1H), 1.58 (d, J = 10.9 Hz, 2H), 1.52 (t, J = 5.3 Hz, 2H), 1.48–1.45 (m, 1H), 1.42 (d, J = 6.9 Hz, 1H), 1.36 (d, J = 10.5 Hz, 1H), 1.25 (s, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.90 (d, J = 5.3 Hz, 6H, H-28, H-21), 0.84–0.81 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 166.06, 161.30, 156.54, 140.78, 135.18, 134.82, 132.37, 131.11, 125.12, 121.56, 114.17, 81.73, 79.54, 71.64, 56.20, 55.49, 51.59, 51.02, 44.59, 42.78, 39.74, 39.28, 36.97, 34.27, 33.07, 32.92, 28.65, 26.07, 23.39, 20.88, 20.61, 19.97, 19.65, 18.04, 17.59, 12.90; HRMS (ESI) m/z: calcd for C39H53NO6 [M + Na]+: 654.3873, found: 654.3770.
White solid (87%). 1H NMR (600 MHz, CDCl3) δ 11.33 (s, 1H, H-N), 8.40 (s, 1H, H-Ar), 7.84–7.77 (m, 3H, H-Ar), 7.58 (dd, J = 8.8, 2.2 Hz, 1H, H-Ar), 7.46 (t, J = 7.7 Hz, 1H, H-Ar), 7.40 (t, J = 7.5 Hz, 1H, H-Ar), 6.52 (d, J = 8.5 Hz, 1H, H-7), 6.47 (d, J = 13.4 Hz, 1H, H-3′), 6.22–6.18 (m, 2H, H-6, H-2′), 5.24–5.20 (m, 1H), 5.16 (td, J = 15.3, 14.4, 6.9 Hz, 2H), 2.27–2.24 (m, 1H), 2.08–2.00 (m, 4H), 1.96 (d, J = 9.5 Hz, 1H), 1.85 (d, J = 6.7 Hz, 1H), 1.77–1.74 (m, 1H), 1.68 (d, J = 8.7 Hz, 1H), 1.59 (t, J = 9.6 Hz, 2H), 1.54–1.50 (m, 2H), 1.48–1.45 (m, 1H), 1.41 (dd, J = 11.4, 5.3 Hz, 1H), 1.36 (d, J = 10.5 Hz, 1H), 1.25 (s, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.91 (d, J = 6.9 Hz, 3H, H-28), 0.89 (s, 3H, H-21), 0.84–0.81 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 166.17, 161.69, 140.93, 135.39, 135.18, 134.80, 133.93, 132.37, 131.13, 130.86, 128.78, 127.89, 127.57, 126.42, 125.42, 125.06, 120.01, 116.84, 81.74, 79.55, 71.83, 56.20, 51.60, 51.05, 44.59, 42.79, 39.74, 39.28, 36.97, 34.30, 33.08, 32.93, 28.66, 26.10, 23.40, 20.89, 20.61, 19.98, 19.66, 18.03, 17.59, 12.91; HRMS (ESI) m/z: calcd for C42H53NO5 [M + Na]+: 674.3924, found: 674.3822.
White solid (83%). 1H NMR (600 MHz, CDCl3) δ 13.38 (s, 1H, H-N), 8.80 (s, 1H, S-CH), 6.49 (d, J = 8.5 Hz, 1H, H-7), 6.18 (d, J = 8.5 Hz, 1H, H-6), 5.21 (dd, J = 15.2, 7.7 Hz, 1H), 5.16–5.12 (m, 1H), 5.00 (dt, J = 11.6, 6.1 Hz, 1H), 3.07 (q, J = 6.3 Hz, 2H, H-3′), 2.79 (t, J = 6.5 Hz, 2H, H-2′), 2.09 (dd, J = 12.9, 6.1 Hz, 1H), 2.03–1.95 (m, 4H), 1.94 (s, 1H), 1.85 (d, J = 6.7 Hz, 1H), 1.76–1.72 (m, 1H), 1.68–1.65 (m, 1H), 1.57–1.53 (m, 2H), 1.48 (d, J = 7.3 Hz, 2H), 1.45 (d, J = 6.5 Hz, 1H), 1.40 (t, J = 6.1 Hz, 1H), 1.37–1.33 (m, 1H), 1.27–1.18 (m, 4H), 0.99 (d, J = 6.5 Hz, 3H, H-18), 0.90 (d, J = 6.8 Hz, 3H, H-28), 0.85–0.80 (m, 12H, H-21, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 171.18, 170.69, 160.45, 147.42, 135.22, 135.03, 132.31, 130.93, 81.70, 79.39, 70.07, 56.17, 51.59, 50.97, 44.55, 42.78, 39.74, 39.29, 36.92, 34.21, 33.07, 30.87, 29.16, 28.64, 26.17, 23.35, 20.90, 20.62, 19.96, 19.65, 18.01, 17.58, 12.88; HRMS (ESI) m/z: calcd for C34H49N3O5S [M + Na]+: 634.3393, found: 634.3295.
White solid (80%). 1H NMR (600 MHz, CDCl3) δ 7.50 (d, J = 3.6 Hz, 1H, N-CH), 6.99 (d, J = 3.6 Hz, 1H, S-CH), 6.50 (d, J = 8.5 Hz, 1H, H-7), 6.20 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.3, 7.6 Hz, 1H), 5.14 (dd, J = 15.3, 8.4 Hz, 1H), 5.02 (tt, J = 11.2, 5.1 Hz, 1H), 2.88 (q, J = 6.6, 6.2 Hz, 2H, H-3′), 2.80–2.74 (m, 2H, H-2′), 2.11 (dd, J = 14.6, 4.4 Hz, 1H), 2.04–1.95 (m, 4H), 1.94 (s, 1H), 1.85 (q, J = 6.8 Hz, 1H), 1.77–1.71 (m, 1H), 1.70–1.66 (m, 1H), 1.58–1.54 (m, 2H), 1.49 (d, J = 9.4 Hz, 2H), 1.47–1.43 (m, 1H), 1.42–1.37 (m, 1H), 1.36–1.31 (m, 1H), 1.26–1.19 (m, 4H), 0.99 (d, J = 6.5 Hz, 3H, H-18), 0.91 (d, J = 6.8 Hz, 3H, H-28), 0.86 (s, 3H, H-21), 0.84–0.80 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 171.36, 169.73, 159.99, 136.25, 135.22, 135.04, 132.32, 130.93, 113.54, 81.72, 79.40, 70.16, 56.17, 51.59, 50.99, 44.56, 42.78, 39.75, 39.30, 36.94, 34.23, 33.07, 30.83, 29.72, 29.14, 28.65, 26.20, 23.37, 20.90, 20.62, 19.97, 19.65, 18.03, 17.59, 12.88; HRMS (ESI) m/z: calcd for C35H50N2O5S [M + H]+: 633.3440, found: 633.3346.
Yellow solid (85%). 1H NMR (600 MHz, CDCl3) δ 7.73 (dd, J = 8.7, 5.1 Hz, 1H, H-Ar), 7.47 (d, J = 9.6 Hz, 1H, H-Ar), 7.07 (td, J = 8.8, 2.5 Hz, 1H, H-Ar), 6.50 (d, J = 8.5 Hz, 1H, H-7), 6.20 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.7 Hz, 1H), 5.14 (dd, J = 15.3, 8.5 Hz, 1H), 5.03 (td, J = 11.4, 5.6 Hz, 1H), 2.82–2.76 (m, 4H, H-3′, H-2′), 2.16–2.12 (m, 1H), 2.00 (q, J = 13.0, 12.5 Hz, 4H), 1.94 (s, 1H), 1.85 (d, J = 6.8 Hz, 1H), 1.76–1.72 (m, 1H), 1.70–1.67 (m, 1H), 1.58–1.55 (m, 2H), 1.51–1.48 (m, 2H), 1.47–1.45 (m, 1H), 1.41–1.38 (m, 1H), 1.34 (d, J = 11.6 Hz, 1H), 1.26–1.21 (m, 4H), 0.99 (d, J = 6.6 Hz, 3H, H-18), 0.91 (d, J = 6.7 Hz, 3H, H-28), 0.87 (s, 3H, H-21), 0.84–0.80 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 171.64, 170.30, 162.85, 161.25, 160.45, 135.21, 135.00, 132.33, 130.95, 127.38, 122.23, 112.34, 107.22, 81.74, 79.43, 70.53, 56.17, 51.58, 50.97, 44.56, 42.78, 39.75, 39.28, 36.94, 34.23, 33.07, 31.20, 29.72, 29.15, 28.65, 26.19, 23.37, 20.89, 20.62, 19.96, 19.65, 18.04, 17.58, 12.88; HRMS (ESI) m/z: calcd for C39H51FN2O5S [M + Na]+: 701.3503, found: 701.3399.
Yellow solid (78%). 1H NMR (600 MHz, CDCl3) δ 7.65 (dd, J = 8.9, 4.6 Hz, 1H, H-Ar), 7.42 (dd, J = 8.0, 2.6 Hz, 1H, H-Ar), 7.09 (td, J = 8.8, 2.6 Hz, 1H, H-Ar), 6.43 (d, J = 8.5 Hz, 1H, H-7), 6.13 (d, J = 8.5 Hz, 1H, H-6), 5.15 (dd, J = 15.2, 7.7 Hz, 1H), 5.07 (dd, J = 15.3, 8.4 Hz, 1H), 4.96 (dt, J = 11.6, 6.1 Hz, 1H), 2.74–2.68 (m, 4H, H-3′, H-2′), 2.06 (dd, J = 13.9, 5.2 Hz, 1H), 1.95 (d, J = 12.8 Hz, 3H), 1.88 (d, J = 11.2 Hz, 2H), 1.79–1.76 (m, 1H), 1.67 (d, J = 10.7 Hz, 1H), 1.62 (d, J = 14.0 Hz, 1H), 1.51–1.49 (m, 2H), 1.42 (t, J = 6.6 Hz, 2H), 1.40–1.38 (m, 1H), 1.34–1.31 (m, 1H), 1.28 (d, J = 11.4 Hz, 1H), 1.19–1.13 (m, 4H), 0.92 (d, J = 6.6 Hz, 3H, H-18), 0.84 (d, J = 6.8 Hz, 3H, H-28), 0.80 (s, 3H, H-21), 0.77–0.73 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 170.63, 169.16, 159.43, 157.81, 156.79, 143.56, 134.17, 133.95, 131.30, 129.94, 120.75, 113.73, 106.80, 80.69, 77.99, 69.49, 55.13, 50.97, 49.94, 43.52, 41.74, 38.71, 38.24, 35.90, 33.19, 32.03, 30.15, 28.12, 27.61, 25.17, 22.33, 19.84, 19.58, 18.93, 18.61, 17.00, 16.54, 11.85; HRMS (ESI) m/z: calcd for C39H51FN2O5S [M + Na]+: 701.3503, found: 701.3402.
White solid (83%). 1H NMR (600 MHz, CDCl3) δ 7.78 (s, 1H, H-N), 7.49 (d, J = 7.8 Hz, 2H, H-Ar), 7.30 (t, J = 7.8 Hz, 2H, H-Ar), 7.08 (t, J = 7.4 Hz, 1H, H-Ar), 6.50 (d, J = 8.5 Hz, 1H, H-7), 6.20 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.6 Hz, 1H), 5.14 (dd, J = 15.3, 8.4 Hz, 1H), 5.02 (dq, J = 11.3, 5.6, 5.1 Hz, 1H), 2.74–2.67 (m, 2H, H-3′), 2.64 (t, J = 7.0 Hz, 2H), H-2′, 2.13 (dd, J = 14.6, 4.3 Hz, 1H), 2.05–1.94 (m, 4H), 1.91 (s, 1H), 1.85 (q, J = 6.8 Hz, 1H), 1.77–1.72 (m, 1H), 1.69 (d, J = 13.7 Hz, 1H), 1.58 (t, J = 7.1 Hz, 2H), 1.52–1.48 (m, 2H), 1.48–1.43 (m, 1H), 1.41–1.37 (m, 1H), 1.37–1.31 (m, 1H), 1.26–1.19 (m, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.91 (d, J = 6.9 Hz, 3H, H-28), 0.87 (s, 3H, H-21), 0.84–0.80 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 172.44, 169.93, 137.92, 135.21, 135.06, 132.33, 130.92, 128.99, 124.20, 119.81, 81.78, 79.45, 70.21, 56.18, 51.61, 51.02, 44.57, 42.78, 39.75, 39.29, 36.95, 34.27, 33.11, 33.07, 32.31, 29.90, 28.65, 26.23, 23.37, 20.89, 20.63, 19.97, 19.65, 18.06, 17.59, 12.89; HRMS (ESI) m/z: calcd for C38H53NO5 [M + Na]+: 626.3924, found: 626.3826.
White solid (81%). 1H NMR (600 MHz, CDCl3) δ 7.85 (s, 1H, H-N), 7.45 (dd, J = 8.9, 4.8 Hz, 2H, H-Ar), 6.98 (t, J = 8.6 Hz, 2H, H-Ar), 6.51 (d, J = 8.5 Hz, 1H, H-7), 6.21 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.6 Hz, 1H), 5.14 (dd, J = 15.2, 8.4 Hz, 1H), 5.03 (tt, J = 11.2, 5.1 Hz, 1H), 2.71 (q, J = 5.8, 5.3 Hz, 2H, H-3′), 2.63 (t, J = 6.5 Hz, 2H, H-2′), 2.13 (dd, J = 13.7, 5.2 Hz, 1H), 2.04–1.95 (m, 4H), 1.92 (d, J = 12.6 Hz, 1H), 1.85 (q, J = 6.8 Hz, 1H), 1.78–1.73 (m, 1H), 1.70 (d, J = 13.6 Hz, 1H), 1.60–1.56 (m, 2H), 1.50 (t, J = 7.6 Hz, 2H), 1.48–1.43 (m, 1H), 1.42–1.38 (m, 1H), 1.37–1.31 (m, 1H), 1.29–1.15 (m, 4H), 1.00 (d, J = 6.5 Hz, 3H, H-18), 0.91 (d, J = 6.8 Hz, 3H, H-28), 0.88 (s, 3H, H-21), 0.84–0.81 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 172.56, 169.91, 158.50, 135.19, 135.01, 133.95, 132.34, 130.97, 121.65, 121.60, 115.65, 115.50, 81.78, 79.48, 70.27, 56.18, 51.61, 51.03, 44.57, 42.78, 39.74, 39.29, 36.95, 34.27, 33.12, 33.07, 32.11, 29.85, 28.65, 26.23, 23.37, 20.89, 20.62, 19.97, 19.65, 18.06, 17.59, 12.88; HRMS (ESI) m/z: calcd for C38H52FNO5 [M + Na]+: 644.3830, found: 644.3722.
White solid (87%). 1H NMR (600 MHz, CDCl3) δ 7.68 (s, 1H, H-N), 7.39 (d, J = 9.0 Hz, 2H, H-Ar), 6.83 (d, J = 8.9 Hz, 2H, H-Ar), 6.50 (d, J = 8.5 Hz, 1H, H-7), 6.21 (d, J = 8.4 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.7 Hz, 1H), 5.14 (dd, J = 15.3, 8.4 Hz, 1H), 5.02 (tt, J = 11.2, 5.1 Hz, 1H), 3.78 (s, 3H, H-OCH3), 2.73–2.67 (m, 2H, H-3′), 2.62 (d, J = 6.6 Hz, 2H, H-2′), 2.15–2.11 (m, 1H), 2.04–1.94 (m, 4H), 1.91 (d, J = 3.2 Hz, 1H), 1.85 (q, J = 6.8 Hz, 1H), 1.77–1.72 (m, 1H), 1.71–1.67 (m, 1H), 1.57 (t, J = 9.2 Hz, 2H), 1.51–1.48 (m, 2H), 1.46 (dd, J = 13.2, 6.6 Hz, 1H), 1.41–1.37 (m, 1H), 1.37–1.31 (m, 1H), 1.29–1.14 (m, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.91 (d, J = 6.8 Hz, 3H, H-28), 0.88 (s, 3H, H-21), 0.84–0.80 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 172.44, 169.73, 156.34, 135.21, 135.07, 132.33, 131.06, 130.91, 121.71, 114.12, 81.79, 79.44, 70.14, 56.18, 55.49, 51.62, 51.03, 44.57, 42.78, 39.75, 39.30, 36.95, 34.27, 33.12, 33.07, 32.07, 29.94, 28.65, 26.23, 23.37, 20.89, 20.63, 19.97, 19.65, 18.06, 17.59, 12.88; HRMS (ESI) m/z: calcd for C39H55NO6 [M + Na]+: 656.4029, found: 656.3922.
White solid (84%). 1H NMR (600 MHz, CDCl3) δ 8.19 (s, 1H, H-N), 7.96 (s, 1H, H-Ar), 7.76 (t, J = 7.1 Hz, 3H, H-Ar), 7.43 (t, J = 7.7 Hz, 2H, H-Ar), 7.38 (t, J = 7.4 Hz, 1H, H-Ar), 6.49 (d, J = 8.5 Hz, 1H, H-7), 6.19 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.3, 7.6 Hz, 1H), 5.14 (dd, J = 15.3, 8.4 Hz, 1H), 5.04 (dq, J = 11.3, 5.7, 5.2 Hz, 1H), 2.75 (q, J = 6.1, 5.4 Hz, 2H, H-3′), 2.70 (d, J = 7.0 Hz, 2H, H-2′), 2.15 (dd, J = 13.7, 3.4 Hz, 1H), 1.99 (ddd, J = 22.2, 16.8, 11.7 Hz, 4H), 1.93 (s, 1H), 1.85 (q, J = 6.8 Hz, 1H), 1.74 (dt, J = 13.4, 3.9 Hz, 1H), 1.70–1.67 (m, 1H), 1.57 (dd, J = 13.2, 10.2 Hz, 2H), 1.51–1.48 (m, 2H), 1.45 (dd, J = 13.2, 6.6 Hz, 1H), 1.41–1.37 (m, 1H), 1.36–1.32 (m, 1H), 1.27–1.17 (m, 4H), 0.99 (d, J = 6.6 Hz, 3H, H-18), 0.91 (d, J = 6.8 Hz, 3H, H-28), 0.87 (s, 3H, H-21), 0.84–0.80 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 172.53, 170.13, 135.36, 135.21, 135.04, 133.86, 132.33, 130.93, 130.61, 128.75, 127.70, 127.54, 126.44, 124.92, 119.86, 116.51, 81.80, 79.46, 70.30, 56.17, 51.61, 51.02, 44.57, 42.78, 39.75, 39.29, 36.95, 34.27, 33.12, 33.07, 32.41, 29.93, 28.65, 26.24, 23.37, 20.89, 20.63, 19.97, 19.65, 18.05, 17.59, 12.88; HRMS (ESI) m/z: calcd for C42H55NO5 [M + Na]+: 676.4080, found: 676.3977.
White solid (78%). 1H NMR (600 MHz, CDCl3) δ 13.39 (s, 1H, H-N), 8.81 (s, 1H. S-CH), 6.50 (d, J = 8.5 Hz, 1H, H-7), 6.20 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.6 Hz, 1H), 5.14 (dd, J = 15.3, 8.4 Hz, 1H), 5.00 (dt, J = 11.7, 6.1 Hz, 1H), 2.84 (t, J = 6.8 Hz, 2H, H-4′), 2.44 (t, J = 7.4 Hz, 2H, H-3′), 2.13 (q, J = 7.2 Hz, 3H, H-2′), 2.00 (t, J = 12.8 Hz, 4H), 1.94 (s, 1H), 1.85 (d, J = 6.7 Hz, 1H), 1.75 (d, J = 9.1 Hz, 1H), 1.68 (d, J = 13.6 Hz, 1H), 1.58–1.54 (m, 2H), 1.50 (d, J = 8.6 Hz, 2H), 1.47–1.45 (m, 1H), 1.42–1.39 (m, 1H), 1.35 (d, J = 9.5 Hz, 1H), 1.26–1.21 (m, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.91 (d, J = 6.8 Hz, 3H, H-28), 0.88 (s, 3H, H-21), 0.84–0.80 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 171.87, 171.32, 160.48, 147.45, 135.21, 135.08, 132.32, 130.94, 81.77, 79.41, 69.60, 56.17, 51.60, 51.00, 44.57, 42.78, 39.75, 39.30, 36.95, 35.10, 34.28, 33.62, 33.15, 33.07, 29.72, 28.65, 26.28, 23.37, 20.89, 20.64, 19.97, 19.65, 18.09, 17.59, 12.88; HRMS (ESI) m/z: calcd for C35H51N3O5S [M + Na]+: 648.3549, found: 648.3449.
White solid (88%). 1H NMR (600 MHz, CDCl3) δ 7.47 (d, J = 3.7 Hz, 1H, H-N), 7.01 (d, J = 3.6 Hz, 1H, H-S), 6.50 (d, J = 8.5 Hz, 1H, H-7), 6.20 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.7 Hz, 1H), 5.14 (dd, J = 15.3, 8.4 Hz, 1H), 5.00 (tt, J = 11.2, 5.1 Hz, 1H), 2.65 (t, J = 7.2 Hz, 2H, H-4′), 2.42 (t, J = 7.1 Hz, 2H, H-3′), 2.10 (q, J = 7.4 Hz, 3H, H-2′), 2.03–1.94 (m, 4H), 1.90 (d, J = 9.4 Hz, 1H), 1.85 (q, J = 6.7 Hz, 1H), 1.76 (td, J = 9.5, 4.5 Hz, 1H), 1.69–1.66 (m, 1H), 1.57 (dd, J = 19.0, 8.0 Hz, 2H), 1.50 (t, J = 7.6 Hz, 2H), 1.47–1.44 (m, 1H), 1.40–1.37 (m, 1H), 1.35 (d, J = 10.4 Hz, 1H), 1.27 (s, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.88 (d, J = 3.8 Hz, 9H, H-28, H-21, H-26), 0.83–0.81 (m, 6H, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 172.01, 170.49, 160.03, 136.22, 135.21, 135.05, 132.32, 130.93, 113.60, 81.74, 79.41, 69.65, 56.17, 51.61, 51.02, 44.56, 42.78, 39.75, 39.30, 36.94, 34.82, 34.28, 33.41, 33.17, 33.07, 29.72, 28.65, 26.30, 23.37, 20.88, 20.62, 19.96, 19.65, 18.06, 17.58, 12.88; HRMS (ESI) m/z: calcd for C36H52N2O5S [M + Na]+: 647.3597, found: 647.3501.
Yellow solid (86%). 1H NMR (600 MHz, CDCl3) δ 7.74 (dd, J = 8.8, 5.1 Hz, 1H, H-Ar), 7.44 (d, J = 7.1 Hz, 1H, H-Ar), 7.08 (td, J = 8.8, 2.4 Hz, 1H, H-Ar), 6.50 (d, J = 8.5 Hz, 1H, H-7), 6.21 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.6 Hz, 1H), 5.14 (dd, J = 15.3, 8.4 Hz, 1H), 5.00 (dt, J = 11.6, 6.2 Hz, 1H), 2.59 (t, J = 7.3 Hz, 2H, H-4′), 2.40 (t, J = 7.1 Hz, 2H, H-3′), 2.12 (d, J = 8.6 Hz, 1H), 2.06 (t, J = 7.2 Hz, 2H, H-2′), 2.00 (t, J = 13.0 Hz, 4H), 1.93 (d, J = 9.5 Hz, 1H), 1.87–1.83 (m, 1H), 1.75 (d, J = 9.1 Hz, 1H), 1.69 (d, J = 13.5 Hz, 1H), 1.59–1.55 (m, 2H), 1.51 (d, J = 6.7 Hz, 2H), 1.48–1.45 (m, 1H), 1.39 (d, J = 5.3 Hz, 1H), 1.35 (d, J = 11.9 Hz, 1H), 1.25 (s, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.89 (d, J = 11.5 Hz, 6H, H-28, H-21), 0.84–0.81 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 172.00, 170.90, 160.58, 135.21, 135.04, 132.33, 130.96, 122.33, 122.27, 112.57, 112.41, 107.21, 107.05, 81.75, 79.44, 69.85, 56.17, 51.59, 50.99, 44.57, 42.78, 39.75, 39.29, 36.95, 35.22, 34.27, 33.23, 33.15, 33.07, 29.72, 28.65, 26.28, 23.38, 20.89, 20.63, 19.97, 19.65, 18.08, 17.59, 12.89; HRMS (ESI) m/z: calcd for C40H53FN2O5S [M + Na]+: 715.3659, found: 715.3562.
Yellow solid (82%). 1H NMR (600 MHz, CDCl3) δ 7.69 (dd, J = 8.9, 4.6 Hz, 1H, H-Ar), 7.51 (dd, J = 8.0, 2.6 Hz, 1H, H-Ar), 7.18 (td, J = 8.9, 2.6 Hz, 1H, H-Ar), 6.51 (d, J = 8.5 Hz, 1H, H-7), 6.22 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.6 Hz, 1H), 5.14 (dd, J = 15.3, 8.4 Hz, 1H), 5.00 (dt, J = 11.7, 6.1 Hz, 1H), 2.59 (t, J = 7.3 Hz, 2H, H-4′), 2.39 (t, J = 7.1 Hz, 2H, H-3′), 2.14–2.10 (m, 1H), 2.06 (t, J = 7.2 Hz, 2H, H-2′), 2.02–1.95 (m, 4H), 1.92 (d, J = 9.1 Hz, 1H), 1.85 (q, J = 6.7 Hz, 1H), 1.75 (d, J = 9.1 Hz, 1H), 1.69 (d, J = 13.6 Hz, 1H), 1.59–1.55 (m, 2H), 1.51 (d, J = 7.4 Hz, 2H), 1.48–1.45 (m, 1H), 1.41–1.38 (m, 1H), 1.35 (d, J = 11.8 Hz, 1H), 1.25 (s, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.91–0.88 (m, 6H, H-28, H-21), 0.84–0.81 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 172.00, 170.87, 158.89, 158.23, 144.00, 135.21, 135.03, 132.78, 132.33, 130.97, 121.44, 114.91, 107.99, 81.75, 79.43, 69.85, 56.18, 51.60, 51.00, 44.57, 42.78, 39.75, 39.29, 36.95, 35.19, 34.27, 33.22, 33.17, 33.07, 29.72, 28.65, 26.30, 23.38, 20.89, 20.63, 19.97, 19.65, 18.08, 17.59, 12.89; HRMS (ESI) m/z: calcd for C40H53FN2O5S [M + Na]+: 715.3659, found: 715.3560.
White solid (81%). 1H NMR (600 MHz, CDCl3) δ 7.56–7.50 (m, 3H, H-N, H-Ar), 7.31 (t, J = 7.7 Hz, 2H, H-Ar), 7.09 (t, J = 7.4 Hz, 1H, H-Ar), 6.51 (d, J = 8.5 Hz, 1H, H-7), 6.22 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.6 Hz, 1H), 5.14 (dd, J = 15.3, 8.4 Hz, 1H), 5.02 (dt, J = 11.8, 6.2 Hz, 1H), 2.41 (dt, J = 14.1, 7.2 Hz, 4H, H-4′, H-3′), 2.14–2.11 (m, 1H), 2.02 (dd, J = 13.5, 5.7 Hz, 6H, H-2′), 1.95 (s, 1H), 1.85 (d, J = 6.7 Hz, 1H), 1.75 (d, J = 9.1 Hz, 1H), 1.70 (d, J = 13.7 Hz, 1H), 1.57 (d, J = 17.8 Hz, 2H), 1.51 (d, J = 8.0 Hz, 2H), 1.48–1.45 (m, 1H), 1.42–1.38 (m, 1H), 1.35 (d, J = 11.8 Hz, 1H), 1.26–1.21 (m, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.92–0.89 (m, 6H, H-28, H-21), 0.84–0.81 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 172.52, 170.62, 137.96, 135.21, 135.05, 132.34, 130.95, 129.00, 124.21, 119.77, 81.78, 79.46, 69.69, 56.18, 51.62, 51.03, 44.57, 42.78, 39.75, 39.30, 36.97, 36.43, 34.29, 33.39, 33.19, 33.07, 29.72, 28.65, 26.31, 23.38, 20.89, 20.63, 19.97, 19.65, 18.09, 17.59, 12.89; HRMS (ESI) m/z: calcd for C39H55NO5 [M + Na]+: 640.4080, found: 640.3985.
White solid (84%). 1H NMR (600 MHz, CDCl3) δ 7.65 (s, 1H, H-N), 7.48 (dd, J = 8.9, 4.8 Hz, 2H, H-Ar), 7.00 (t, J = 8.5 Hz, 2H, H-Ar), 6.51 (d, J = 8.5 Hz, 1H, H-7), 6.22 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.6 Hz, 1H), 5.14 (dd, J = 15.3, 8.4 Hz, 1H), 5.01 (tt, J = 11.3, 5.1 Hz, 1H), 2.43–2.38 (m, 4H, H-4′, H-3′), 2.14–2.10 (m, 1H), 2.05–1.97 (m, 6H, H-2′), 1.95 (s, 1H), 1.85 (q, J = 6.8 Hz, 1H), 1.77–1.73 (m, 1H), 1.72–1.69 (m, 1H), 1.57 (d, J = 10.6 Hz, 2H), 1.51 (d, J = 9.3 Hz, 2H), 1.48–1.45 (m, 1H), 1.39 (d, J = 5.2 Hz, 1H), 1.35 (d, J = 12.9 Hz, 1H), 1.26–1.21 (m, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.92–0.89 (m, 6H, H-28, H-21), 0.83 (dd, J = 8.8, 5.6 Hz, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 172.59, 170.64, 160.10, 135.19, 135.02, 134.00, 132.35, 130.98, 121.64, 121.58, 115.66, 115.51, 81.79, 79.48, 69.74, 56.18, 51.61, 51.03, 44.57, 42.78, 39.74, 39.29, 36.97, 36.24, 34.29, 33.38, 33.18, 33.07, 29.72, 28.65, 26.31, 23.37, 20.89, 20.82, 19.97, 19.65, 18.08, 17.59, 12.88; HRMS (ESI) m/z: calcd for C39H54FNO5 [M + Na]+: 658.3986, found: 658.3886.
White solid (78%). 1H NMR (600 MHz, CDCl3) δ 7.47 (s, 1H, H-N), 7.41 (d, J = 8.5 Hz, 2H, H-Ar), 6.84 (d, J = 8.8 Hz, 2H, H-Ar), 6.51 (d, J = 8.5 Hz, 1H, H-7), 6.22 (d, J = 8.5 Hz, 1H, H-6), 5.22 (dd, J = 15.2, 7.6 Hz, 1H), 5.14 (dd, J = 15.3, 8.4 Hz, 1H), 5.01 (dq, J = 11.8, 6.1, 5.7 Hz, 1H), 3.78 (s, 3H, H-OCH3), 2.39 (t, J = 7.1 Hz, 4H, H-4′, H-3′), 2.12 (dd, J = 14.3, 5.0 Hz, 1H), 2.05–1.97 (m, 6H, H-2′), 1.95 (s, 1H), 1.87–1.83 (m, 1H), 1.75 (d, J = 9.1 Hz, 1H), 1.70 (d, J = 13.8 Hz, 1H), 1.57 (d, J = 11.2 Hz, 2H), 1.51 (d, J = 9.2 Hz, 2H), 1.48–1.44 (m, 1H), 1.40 (t, J = 5.8 Hz, 1H), 1.35 (d, J = 12.9 Hz, 1H), 1.26–1.21 (m, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.92–0.88 (m, 6H, H-28, H-21), 0.84–0.81 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 172.51, 170.43, 156.35, 135.21, 135.06, 132.33, 131.07, 130.94, 121.70, 114.12, 81.78, 79.45, 69.65, 56.18, 55.49, 51.61, 51.03, 44.57, 42.78, 39.75, 39.30, 36.96, 36.24, 34.29, 33.44, 33.19, 33.07, 29.72, 28.65, 26.31, 23.37, 20.92, 20.89, 19.97, 19.65, 18.08, 17.59, 12.88; HRMS (ESI) m/z: calcd for C40H57NO6 [M + Na]+: 670.4186, found: 670.4091.
White solid (82%). 1H NMR (600 MHz, CDCl3) δ 8.23 (s, 1H, H-N), 7.78–7.75 (m, 4H, H-Ar), 7.44 (t, J = 9.7 Hz, 2H, H-Ar), 7.39 (d, J = 7.6 Hz, 1H, H-Ar), 6.50 (d, J = 8.5 Hz, 1H, H-7), 6.21 (d, J = 8.5 Hz, 1H, H-6), 5.23–5.20 (m, 1H), 5.16–5.12 (m, 1H), 5.03 (dt, J = 11.7, 6.1 Hz, 1H), 2.47 (d, J = 7.3 Hz, 2H, H-4′), 2.43 (t, J = 7.0 Hz, 2H, H-3′), 2.13 (d, J = 8.6 Hz, 1H), 2.08–2.00 (m, 6H, H-2′), 1.94 (s, 1H), 1.85 (d, J = 6.8 Hz, 1H), 1.76–1.73 (m, 1H), 1.71 (s, 1H), 1.57 (d, J = 12.0 Hz, 2H), 1.50 (d, J = 6.4 Hz, 2H), 1.47–1.45 (m, 1H), 1.40 (dd, J = 11.6, 5.3 Hz, 1H), 1.35 (d, J = 12.1 Hz, 1H), 1.26–1.22 (m, 4H), 1.00 (d, J = 6.6 Hz, 3H, H-18), 0.91 (d, J = 6.8 Hz, 3H, H-28), 0.88 (s, 3H, H-21), 0.84–0.81 (m, 9H, H-26, H-27, H-19); 13C NMR (150 MHz, CDCl3) δ 172.57, 170.84, 135.41, 135.21, 135.05, 133.88, 132.34, 130.96, 130.61, 128.76, 127.70, 127.56, 126.48, 124.95, 119.84, 116.49, 81.79, 79.46, 69.73, 56.18, 51.61, 51.03, 44.57, 42.79, 39.75, 39.29, 36.97, 36.48, 34.30, 33.41, 33.20, 33.07, 29.72, 28.65, 26.33, 23.37, 20.89, 19.98, 19.66, 18.08, 17.59, 12.89; HRMS (ESI) m/z: calcd for C43H57NO5 [M + Na]+: 690.4237, found: 690.4139.
White solid (77%). 1H NMR (600 MHz, CDCl3) δ 8.77 (s, 1H, H-N), 8.01 (d, J = 7.6 Hz, 1H, S-CH), 7.64 (ddd, J = 29.0, 15.0, 7.4 Hz, 4H, H-Ar), 6.47 (d, J = 8.5 Hz, 1H, H-7), 6.10 (d, J = 8.5 Hz, 1H, H-6), 5.21 (d, J = 4.6 Hz, 1H), 5.16–5.12 (m, 2H), 2.12 (d, J = 8.3 Hz, 1H), 2.00–1.94 (m, 4H), 1.92 (s, 1H), 1.85 (s, 1H), 1.74 (d, J = 8.4 Hz, 1H), 1.69 (dd, J = 13.5, 3.8 Hz, 1H), 1.56 (s, 2H), 1.46 (s, 2H), 1.41–1.39 (m, 1H), 1.37 (s, 1H), 1.33 (s, 1H), 1.25 (s, 4H), 0.99 (s, 3H, H-18), 0.91 (d, J = 6.9 Hz, 3H, H-28), 0.83–0.80 (m, 9H, H-21, H-26, H-27), 0.72 (s, 3H, H-19); 13C NMR (150 MHz, CDCl3) δ 167.12, 165.13, 159.74, 147.49, 135.43, 135.22, 134.93, 132.32, 131.03, 130.94, 130.76, 130.70, 129.98, 128.07, 81.60, 79.39, 71.23, 56.19, 51.68, 51.07, 44.54, 42.78, 39.74, 39.27, 36.96, 34.11, 33.07, 32.81, 28.67, 25.91, 23.40, 20.89, 20.61, 19.96, 19.65, 18.19, 17.59, 12.87; HRMS (ESI) m/z: calcd for C38H49N3O5S [M + Na]+: 682.3393, found: 682.3285.
White solid (86%). 1H NMR (600 MHz, CDCl3) δ 8.13–8.11 (m, 1H, N-CH), 7.65 (td, J = 4.5, 2.0 Hz, 2H, H-Ar), 7.59–7.57 (m, 1H, S-CH), 6.77 (d, J = 3.7 Hz, 1H, H-Ar), 6.44 (d, J = 8.5 Hz, 1H, H-7), 6.09 (d, J = 3.6 Hz, 1H, H-Ar), 6.02 (d, J = 8.5 Hz, 1H, H-6), 5.21 (dd, J = 15.3, 7.7 Hz, 1H), 5.16–5.09 (m, 2H), 2.00 (dd, J = 13.2, 4.9 Hz, 2H), 1.92 (dt, J = 13.5, 3.4 Hz, 2H), 1.84 (q, J = 6.8 Hz, 2H), 1.78 (d, J = 12.0 Hz, 1H), 1.75–1.72 (m, 1H), 1.58 (s, 1H), 1.56–1.51 (m, 2H), 1.46–1.43 (m, 2H), 1.36 (d, J = 6.8 Hz, 1H), 1.33 (s, 1H), 1.25 (s, 1H), 1.24–1.09 (m, 4H), 0.99 (d, J = 6.6 Hz, 3H, H-18), 0.90 (d, J = 6.8 Hz, 3H, H-28), 0.83–0.78 (m, 9H, H-21, H-26, H-27), 0.61 (s, 3H, H-19); 13C NMR (150 MHz, CDCl3) δ 167.49, 164.50, 160.02, 136.59, 136.07, 135.21, 134.97, 132.53, 132.32, 130.86, 130.84, 130.36, 129.11, 128.11, 113.07, 81.54, 79.33, 71.06, 56.15, 51.54, 50.89, 44.53, 42.78, 39.74, 39.26, 36.84, 34.09, 33.07, 32.65, 28.63, 25.75, 23.32, 20.89, 20.61, 19.97, 19.65, 17.75, 17.59, 12.87; HRMS (ESI) m/z: calcd for C39H50N2O5S [M + Na]+: 681.3440, found: 681.3334.
Yellow solid (82%). 1H NMR (600 MHz, CDCl3) δ 7.91–7.89 (m, 1H, H-Ar), 7.70 (dd, J = 8.7, 5.1 Hz, 1H, H-Ar), 7.55–7.53 (m, 1H, H-Ar), 7.49–7.46 (m, 2H, H-Ar), 7.00 (t, J = 7.5 Hz, 1H, H-Ar), 6.50 (d, J = 9.4 Hz, 1H, H-Ar), 6.42 (d, J = 8.5 Hz, 1H, H-7), 5.99 (d, J = 8.5 Hz, 1H, H-6), 5.22–5.18 (m, 1H), 5.12 (dd, J = 15.3, 8.8 Hz, 2H), 2.13 (dd, J = 13.8, 5.1 Hz, 1H), 1.99–1.94 (m, 3H), 1.93–1.89 (m, 2H), 1.84 (d, J = 6.8 Hz, 1H), 1.72 (d, J = 9.5 Hz, 1H), 1.60 (d, J = 14.4 Hz, 1H), 1.51 (d, J = 7.1 Hz, 2H), 1.43 (d, J = 9.1 Hz, 2H), 1.34 (d, J = 8.7 Hz, 1H), 1.26 (s, 2H), 1.20–1.10 (m, 4H), 0.97 (d, J = 6.5 Hz, 3H, H-18), 0.90 (d, J = 6.8 Hz, 3H, H-28), 0.83–0.80 (m, 6H, H-21, H-26), 0.77 (s, 3H, H-27), 0.66 (s, 3H, H-19); 13C NMR (150 MHz, CDCl3) δ 167.87, 164.92, 161.64, 135.52, 135.21, 134.86, 132.48, 132.30, 130.88, 130.70, 129.55, 127.72, 126.72, 121.94, 121.88, 112.48, 112.32, 106.67, 106.50, 81.59, 79.33, 71.42, 56.14, 51.53, 50.89, 44.52, 42.77, 39.73, 39.23, 36.87, 34.12, 33.07, 32.73, 28.62, 25.96, 23.31, 20.87, 20.59, 19.96, 19.65, 17.73, 17.58, 12.86; HRMS (ESI) m/z: calcd for C43H51FN2O5S [M + H]+: 727.3503, found: 727.3580.
Yellow solid (80%). 1H NMR (600 MHz, CDCl3) δ 7.96–7.92 (m, 1H, N-H), 7.58–7.56 (m, 1H, H-Ar), 7.53–7.48 (m, 4H, H-Ar), 7.14 (dd, J = 8.9, 4.5 Hz, 1H, H-Ar), 7.00–6.98 (m, 1H, H-Ar), 6.43 (d, J = 8.5 Hz, 1H, H-7), 5.99 (d, J = 8.5 Hz, 1H, H-6), 5.22–5.19 (m, 1H), 5.17–5.10 (m, 2H), 2.15–2.12 (m, 1H), 1.98 (dd, J = 15.6, 7.8 Hz, 4H), 1.92 (s, 1H), 1.84 (d, J = 6.8 Hz, 1H), 1.73 (d, J = 8.8 Hz, 1H), 1.62 (d, J = 3.7 Hz, 1H), 1.59 (d, J = 12.7 Hz, 2H), 1.53 (d, J = 11.7 Hz, 2H), 1.47 (d, J = 6.3 Hz, 1H), 1.43 (s, 1H), 1.41 (s, 1H), 1.26 (s, 4H), 0.98 (d, J = 6.6 Hz, 3H, H-18), 0.90 (d, J = 6.9 Hz, 3H, H-28), 0.83–0.80 (m, 6H, H-21, H-26,), 0.77 (s, 3H, H-27), 0.64 (s, 3H, H-19); 13C NMR (150 MHz, CDCl3) δ 167.61, 165.00, 160.43, 158.80, 135.35, 135.20, 134.83, 132.53, 132.39, 132.32, 130.91, 130.76, 129.59, 127.80, 121.27, 114.76, 114.60, 107.67, 107.50, 81.61, 79.36, 71.46, 56.15, 51.54, 50.90, 44.53, 42.78, 39.73, 39.24, 36.87, 34.13, 33.07, 32.74, 28.62, 25.94, 23.32, 20.87, 20.59, 19.96, 19.65, 17.69, 17.58, 12.86; HRMS (ESI) m/z: calcd for C43H51FN2O5S [M + H]+: 727.3503, found: 727.3607.
White solid (82%). 1H NMR (600 MHz, CDCl3) δ 7.97 (d, J = 7.9 Hz, 1H, H-N), 7.74 (s, 1H, H-Ar), 7.65 (d, J = 8.0 Hz, 2H, H-Ar), 7.58–7.50 (m, 3H, H-Ar), 7.35 (t, J = 7.9 Hz, 2H, H-Ar), 7.13 (t, J = 7.4 Hz, 1H, H-Ar), 6.42 (d, J = 8.5 Hz, 1H, H-7), 5.95 (d, J = 8.5 Hz, 1H, H-6), 5.21 (dd, J = 15.2, 7.6 Hz, 1H), 5.13 (dd, J = 15.5, 8.4 Hz, 2H), 2.00 (s, 1H), 1.99–1.91 (m, 4H), 1.85 (d, J = 6.2 Hz, 1H), 1.83–1.80 (m, 1H), 1.72 (d, J = 9.5 Hz, 1H), 1.59 (d, J = 14.0 Hz, 1H), 1.47–1.44 (m, 2H), 1.42 (d, J = 11.5 Hz, 2H), 1.36 (d, J = 7.6 Hz, 1H), 1.32 (d, J = 11.9 Hz, 1H), 1.25 (s, 1H), 1.17 (p, J = 12.9, 11.6 Hz, 4H), 0.98 (d, J = 6.6 Hz, 3H, H-18), 0.90 (d, J = 6.9 Hz, 3H, H-28), 0.82 (dd, J = 10.1, 6.8 Hz, 6H, H-21, H-26), 0.78 (s, 3H, H-27), 0.63 (s, 3H, H-19); 13C NMR (150 MHz, CDCl3) δ 167.65, 165.47, 138.42, 138.29, 135.21, 135.08, 132.32, 130.67, 129.80, 129.17, 128.76, 127.63, 124.36, 119.41, 81.70, 79.38, 71.17, 56.15, 51.50, 50.89, 44.52, 42.78, 39.72, 39.27, 36.86, 34.09, 33.07, 32.83, 28.62, 25.90, 23.29, 20.87, 20.61, 19.97, 19.65, 17.79, 17.59, 12.84; HRMS (ESI) m/z: calcd for C42H53NO5 [M + Na]+: 674.3924, found: 674.3822.
White solid (78%). 1H NMR (600 MHz, CDCl3) δ 7.94 (d, J = 7.8 Hz, 1H, N-H), 7.84 (s, 1H, H-Ar), 7.63 (dd, J = 8.8, 4.7 Hz, 2H, H-Ar), 7.58–7.54 (m, 2H, H-Ar), 7.50 (t, J = 6.7 Hz, 1H, H-Ar), 7.05 (t, J = 8.6 Hz, 2H, H-Ar), 6.45 (d, J = 8.5 Hz, 1H, H-7), 6.01 (d, J = 8.4 Hz, 1H, H-6), 5.21 (dd, J = 15.2, 7.6 Hz, 1H), 5.14 (dd, J = 15.3, 8.3 Hz, 2H), 2.05–2.02 (m, 1H), 1.99–1.92 (m, 4H), 1.86 (d, J = 6.5 Hz, 1H), 1.84 (d, J = 6.3 Hz, 1H), 1.73–1.70 (m, 1H), 1.62 (d, J = 10.3 Hz, 1H), 1.53–1.48 (m, 2H), 1.45 (d, J = 7.1 Hz, 2H), 1.38 (dd, J = 11.5, 5.0 Hz, 1H), 1.35 (s, 1H), 1.33 (d, J = 11.0 Hz, 1H), 1.25 (s, 4H), 0.99 (d, J = 6.5 Hz, 3H, H-18), 0.91 (d, J = 6.9 Hz, 3H, H-28), 0.82 (dd, J = 10.0, 6.7 Hz, 6H, H-21, H-26), 0.78 (s, 3H, H-27), 0.69 (s, 3H, H-19); 13C NMR (150 MHz, CDCl3) δ 167.52, 165.58, 160.18, 158.56, 138.06, 135.20, 134.95, 132.34, 132.29, 130.86, 130.58, 129.88, 128.82, 127.76, 121.25, 121.20, 115.84, 115.69, 81.72, 79.45, 71.22, 56.15, 51.50, 50.90, 44.54, 42.79, 39.71, 39.26, 36.89, 34.10, 33.07, 32.90, 28.62, 25.96, 23.31, 20.87, 20.60, 19.97, 19.65, 17.80, 17.59, 12.85; HRMS (ESI) m/z: calcd for C42H52FNO5 [M + Na]+: 692.3830, found: 692.3731.
White solid (80%). 1H NMR (600 MHz, CDCl3) δ 7.92 (d, J = 7.7 Hz, 1H, H-N), 7.69 (s, 1H, H-Ar), 7.59–7.55 (m, 4H, H-Ar), 7.50–7.47 (m, 1H, H-Ar), 6.89 (d, J = 8.9 Hz, 2H, H-Ar), 6.44 (d, J = 8.5 Hz, 1H, H-7), 6.02 (d, J = 8.5 Hz, 1H, H-6), 5.21 (dd, J = 15.2, 7.7 Hz, 1H), 5.14 (dd, J = 15.7, 8.0 Hz, 2H), 3.81 (s, 3H, H-OCH3), 2.05 (dd, J = 13.8, 5.1 Hz, 1H), 1.97–1.88 (m, 4H), 1.86–1.83 (m, 1H), 1.73 (d, J = 9.4 Hz, 1H), 1.63–1.60 (m, 1H), 1.56 (d, J = 9.5 Hz, 1H), 1.50 (d, J = 7.7 Hz, 2H), 1.48–1.45 (m, 2H), 1.43 (s, 1H), 1.37 (d, J = 9.7 Hz, 1H), 1.33 (d, J = 9.9 Hz, 1H), 1.26–1.15 (m, 4H), 0.99 (d, J = 6.6 Hz, 3H, H-18), 0.91 (d, J = 6.8 Hz, 3H, H-28), 0.84–0.81 (m, 6H, H-21, H-26), 0.79 (s, 3H, H-27), 0.68 (s, 3H, H-19); 13C NMR (150 MHz, CDCl3) δ 167.34, 165.70, 156.42, 138.32, 135.21, 135.06, 132.32, 132.22, 131.65, 130.73, 130.50, 129.73, 127.72, 121.14, 114.29, 81.73, 79.39, 71.16, 56.15, 51.55, 50.94, 44.54, 42.78, 39.73, 39.27, 36.88, 34.15, 33.07, 32.86, 28.63, 25.93, 23.32, 20.88, 20.61, 19.97, 19.65, 17.79, 17.59, 12.86; HRMS (ESI) m/z: calcd for C43H55NO6 [M + Na]+: 704.4029, found: 704.3925.
White solid (83%). 1H NMR (600 MHz, CDCl3) δ 8.43 (s, 1H, H-N), 7.99 (d, J = 7.8 Hz, 1H, H-Ar), 7.86 (s, 1H, H-Ar), 7.81 (d, J = 9.8 Hz, 3H, H-Ar), 7.61 (d, J = 4.4 Hz, 2H, H-Ar), 7.53–7.47 (m, 3H, H-Ar), 7.42 (d, J = 7.4 Hz, 1H, H-Ar), 6.34 (d, J = 8.5 Hz, 1H, H-7), 5.79 (d, J = 8.5 Hz, 1H, H-6), 5.22–5.18 (m, 1H), 5.15–5.10 (m, 2H), 2.02 (d, J = 8.4 Hz, 1H), 1.94–1.84 (m, 4H), 1.83 (d, J = 7.1 Hz, 1H), 1.70 (d, J = 9.3 Hz, 1H), 1.54 (d, J = 5.9 Hz, 1H), 1.52 (s, 1H), 1.46 (d, J = 6.6 Hz, 2H), 1.35 (d, J = 12.1 Hz, 2H), 1.32 (d, J = 4.8 Hz, 1H), 1.29 (s, 1H), 1.25 (s, 1H), 1.18–1.03 (m, 4H), 0.96 (d, J = 6.5 Hz, 3H, H-18), 0.90 (d, J = 6.8 Hz, 3H, H-28), 0.83–0.80 (m, 6H, H-21, H-26), 0.74 (s, 3H, H-27), 0.47 (s, 3H, H-19); 13C NMR (150 MHz, CDCl3) δ 167.74, 165.58, 138.22, 135.73, 135.20, 134.90, 133.95, 132.36, 132.30, 130.71, 130.61, 129.92, 128.99, 128.87, 127.75, 127.70, 127.58, 126.66, 125.11, 119.47, 116.25, 81.64, 79.33, 71.24, 56.12, 51.50, 50.87, 44.50, 42.78, 39.71, 39.22, 36.77, 34.09, 33.07, 32.82, 28.60, 25.91, 23.25, 20.86, 20.58, 19.96, 19.64, 17.58, 17.49, 12.83; HRMS (ESI) m/z: calcd for C46H55NO5 [M + Na]+: 724.4080, found: 724.3981.