# School of Pharmaceutical Sciences, Zhengzhou University, 100 Kexue Avenue, Zhengzhou, Henan , China.
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- Πολύδωρος Αλεξάκης
- 5 χρόνια πριν
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1 upporting Information Triazole-dithiocarbamate based LD1 selective inactivators inhibit gastric cancer cell growth, invasion and migration Yi-Chao Zheng, #, Ying-Chao Duan, #, Jin-Lian Ma, # Rui-Min Xu, # Xiaolin Zi, Wen-Lei Lv, # Meng-Meng Wang, # Xian-Wei Ye, # hun Zhu, David Mobley, Yan-Yan Zhu, Jun- Wei Wang, # Jin-eng Li, # Zhi-Ru Wang, # Wen Zhao, # Hong-Min Liu #,* # chool of Pharmaceutical ciences, Zhengzhou University, 100 Kexue Avenue, Zhengzhou, Henan , China. ew Drug Research & Development Center, Zhengzhou University, 100 Kexue Avenue, Zhengzhou, Henan , China. ǁ The College of Chemistry and Molecular Engineering, Zhengzhou University, 100 Kexue Avenue, Zhengzhou, Henan , China. ǁ Departments of Urology, Pharmacology and Pharmaceutical ciences, University of California, Irvine, range, UA. Department of Pharmaceutical ciences, University of California, Irvine, UA. Table of content Compound characterization 1
2 Compound characterization Prop-2-ynyl 4-phenylpiperazine-1-carbodithioate (4g): found: Yield 72.4%, red oil. 1 H MR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 3H), 4.49 (brs, 2H), 4.17 (d, J = 2.7 Hz, 2H), 4.11 (brs, 2H), 3.35 (t, J = 5.3 Hz, 4H), 2.30 (t, J = 2.7 Hz, 1H); 13 C MR (101 MHz, CDCl 3 ) δ , , , , , 78.34, 71.83, 48.76, 26.02; HRM (EI) calcd for C 14 H [M + H] + : , Prop-2-ynyl 4-(pyrimidin-2-yl)piperazine-1-carbodithioate (4h): Yield 81.0%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 8.35 (d, J = 4.8 Hz, 2H), 6.59 (t, J = 4.8 Hz, 1H), 4.40 (brs, 2H), 4.15 (d, J = 2.7 Hz, 2H), (m, 6H), 2.28 (t, J = 2.7 Hz, 1H); 13 C MR (101 MHz, CDCl 3 ) δ , , , , 78.29, 71.81, 42.93, 25.97; HRM (EI) calcd for C 12 H 14 4 a 2 [M + a] + : , found: Prop-2-ynyl 4-(methylsulfonyl)piperazine-1-carbodithioate (4i): Yield 77.2%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 4.27 (brs, 4H), 4.12 (d, J = 2.6 Hz, 2H), 3.36 (t, J = 5.2 Hz, 4H), 2.82 (s, 3H), 2.28 (t, J = 2.6 Hz, 1H); 13 C MR (101 MHz, CDCl 3 ) δ , 77.91, 72.04, 45.24, 35.14, 26.23; HRM (EI) calcd for C 9 H 14 2 a 2 3 [M + a] + : , found: (azidomethyl)naphthalene (5e): Yield 81.5%, yellow white solid. Mp: o C; 1 HMR (400 MHz, Acetone-d 6, ppm): δ (m, 4H), (m, 3H), 4.63 (s, 2H); 13 C 3 MR (100 MHz, Acetone-d 6, ppm): δ 133.5, 133.4, 133.2, 128.6, 127.9, 127.7, 127.2, 126.4, 126.3, 126.2, 54.4; HRM (EI) calcd for C 11 H 10 3 [M + H] + : , found: (azidomethyl)-1H-benzo[d]imidazole (5f): Yield 80.4%, yellow white solid. Mp: o C; 1 H MR (400 MHz, Acetone-d 6, ppm): δ 11.7 (brs, 1H), 7.60 (dd, J 1 = 3.2 Hz, J 2 = 6.0 Hz, 2H), 7.24 (dd, J 1 = 3.2 Hz, J 2 = 6.0 Hz, 2H), 4.73 (s, 2H); 13 C MR (100 MHz, Acetone-d 6, ppm): δ 149.2, 139.0, 122.3, 115.3, 47.8; HRM (EI) calcd for C 8 H 8 5 [M + H] + : , found: (azidomethyl)quinolin-2(1H)-one (5g): 3 H Yield 79.9%, yellow white solid Mp: o C; 1 HMR (400 MHz, Acetone-d 6, ppm): δ (brs, 1H), 7.78 (dd, J 1 = 1.0 Hz, J 2 = 8.1 Hz, 1H), (m, 1H), 7.46 (d, J 1 = 8.1 Hz, 1H), (m, 1H), 6.66 (s, 1H), 4.81 (s, 2H); 13 C MR (100 MHz, Acetone-d 6, ppm): δ 161.5, 145.1, 139.4, 130.7, 124.3, 122.1, , 117.8, 115.8, 50.9; HRM (EI) calcd for C 10 H 9 4 [M + H] + : , found: (1-(2-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl piperidine-1-carbodithioate (12): Yield 71.8%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.68 (s, 1H), (m, 1H), (m, 1H), (m, 2H), 5.54 (s, 2H), 4.67 (s, 2H), 4.26 (brs, 2H), 3.84 (brs, 2H), H 3 2
3 1.78 (m, 2H), (m, 4H); HRM (EI) calcd for C 16 H [M + a] + : , found: (1-(4-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl piperidine-1-carbodithioate (13): Yield 89.9%, white solid. Mp: o C; 1 H MR (400 MHz, Acetone) δ 7.99 (s, 1H), (m, 2H), (m, 2H), 5.63 (s, 2H), 4.62 (s, 2H), 4.29 (brs, 2H), 3.90 (brs, 2H), (m, 2H), (m, 4H); HRM (EI) calcd for C 16 H 19 4 a 2 [M + a] + : , found: (1-(4-Methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl piperidine-1-carbodithioate (14): Yield 75.9%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.60 (s, H), 7.17 (s, 4H), 5.44 (s, 2H), 4.68 (s, 2H), 4.28 (brs, 2H), 3.85 (brs, 2H), 2.36 (s, 3H), (m, 2H), (m, 4H); 13 C MR (101 MHz, CDCl 3 ) δ , , , , , , 53.94, 31.95, 25.99, 25.47, 24.23, 21.16; HRM (EI) calcd for C 17 H 22 4 a 2 [M+ a] + : , found: (1-(2-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl morpholine-4-carbodithioate (18): Yield 75.4%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.68 (s, 1H), (m, 1H), (m, 1H), (m, 1H), 5.56 (s, 2H), 4.71 (s, 2H), 4.33 (brs, 2H), 3.94 (brs, 2H), 3.76 (s, 4H); 13 C MR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , 66.19, 47.67, 47.62, 31.68; HRM (EI) calcd for C 15 H 17 4 a 2 [M + a] + : , found: (1-(4-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl morpholine-4-carbodithioate (19): Yield 79.3%, white solid. Mp: o C; 1 H MR (400 MHz, Acetone) δ 8.00 (s, 1H), (m, 2H), (m, 2H), 5.64 (s, 2H), 4.64 (s, 2H), 4.28 (brs, 2H), 3.96 (brs, 2H), 3.74 (t, J = 4.9 Hz, 4H); HRM (EI) calcd for C 15 H 17 4 a 2 [M + a] + : , found: tert Butyl 4-(((1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)methylthio)carbonothioyl)- piperazine-1-carboxylate (25): Cl Yield 85.5%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.59 (s, 1H), 7.35 (d, 2H, J = 8.4 Hz), 7.20 (d, J = 8.4 Hz, 2H), 5.45 (s, 2H), 4.68 (s, 2H), 4.29 (brs, 2H), 3.90 (brs, 2H), 3.54 (t, J = 5.2 Hz, 4H), 1.47 (s, 9H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , 80.69, 53.40, 31.72, 28.35; HRM (EI) calcd for C 20 H 27 Cl [M + H] + : , found: tert Butyl 4-(((1-(3-methylbenzyl)-1H-1,2,3-triazol-4 yl)methylthio) carbonothioyl)- piperazine-1-carboxylate (28): Yield 87.8%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.61 (s, 1H), 7.25 (d, J = 7.5 Hz, 1H), 7.16 (d, J = 7.5 Hz, 1H), 7.07 (s, 2H), 5.44 (s, 2H), 4.68 (s, 2H), 4.30 (brs, 2H), 3.90 (brs, 2H), 3.52 (s, 4H), 2.34 (s, 3H), CH 3 3
4 1.47 (s, 9H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , 80.64, 54.22, 31.90, 28.36, 21.36; HRM (EI) calcd for C 21 H [M + H] + : , found: tert Butyl 4-(((1-(2-methylbenzyl)-1H-1,2,3-triazol-4-yl)methylthio)carbonothioyl)- piperazine-1-carboxylate (29): Yield 82.9%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.48 (s, 1H), CH (m, 4H), 5.50 (s, 2H),4.67 (s, 2H), 4.30 (brs, 2H), 3.91 (brs, 2H), 3.54 (t, J = 5.0 Hz, 3H), 2.29 (s, 3H), 1.48 (s, 3H); 13 C MR (100 MHz, CDCl 3, ppm): δ196.39, , , , , , , , 80.63, 52.36, 31.91, 28.36, 19.05; HRM (EI) calcd for C 21 H [M + H] + : , found: tert Butyl 4-(((1-(4-(trifluoromethyl)benzyl)-1H-1,2,3-triazol-4-yl)methylthio) carbonothioyl) piperazine-1- carboxylate (30): Yield 88.1%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.65 (s, 1H), 7.64 (d, J = 8.0 Hz, 2H), 7.37 (d, J = 8.0 Hz, 2H), 5.55 (s, 2H), 4.70 (s, 2H), 3 C 4.31 (brs, 2H), 3.91 (brs, 2H), 3.53 (s, 4H), 1.47 (s, 9H); HRM (EI) calcd for C 21 H [M + H] + : , found: tert Butyl 4-(((1-(2-(trifluoromethyl)benzyl)-1H-1,2,3-triazol-4-yl)methylthio) carbonothioyl) piperazine-1-carboxylate (31): Yield 87.5%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.73 (d, J = 7.7 Hz, 1H), 7.63 (s, 1H), (m, 2H), 7.15 (d, J = 7.7 Hz, 1H), 5.71 (s, 2H), 4.71 (s, 2H), C (brs, 2H), 3.91 (brs, 2H), 3.54 (t, J = 5.0 Hz, 4H), 1.47 (s, 9H); HRM (EI) calcd for C 21 H [M + H] + : , found: tert Butyl 4-(((1-(4-hydroxybenzyl)-1H-1,2,3-triazol-4-yl)methylthio)carbonothioyl) piperazine-1-carboxylate (33): Yield 77.3%, white solid. Mp: o C; 1 H MR (400 MHz, DM-d 6 ) δ 9.54 (s, 1H), 8.04 (s, 1H), 7.18 (d, J = 8.3 Hz, 2H), 6.75 (d, J = 8.3 Hz, 2H), 5.41 (s, 2H), 4.55 (s, 2H), 4.22 (brs, 2H), 3.89 (brs, 2H), 3.44 (s, 4H), 1.41 (s, H 9H); 13 C MR (101 MHz, DM) δ , , , , , , , , 79.86, 52.98, 31.97, 28.48; HRM (EI) calcd for C 20 H 27 5 a 3 2 [M + a] + : , found: tert Butyl 4-(((1-(2-hydroxybenzyl)-1H-1,2,3-triazol-4-yl)methylthio)carbonothioyl) piperazine-1-carboxylate (34): Yield 82.4%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.62 (s, 1H), (m, 1H), (m, 2H), 6.82 (d, J = 7.7 Hz, 1H), 5.41 (s, 2H), 4.65 (s, 2H), 4.29 (brs, 2H), 3.87 (brs, 2H), 3.51 (s, 4H), 1.47 (s, 9H); 13 C MR H (101 MHz, CDCl 3 ) δ , , , , , , , , , , 80.80, 54.31, 31.44, 28.36; HRM (EI) calcd for C 20 H 27 5 a 3 2 [M + a] + : 4
5 , found: tert Butyl 4-(((1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methylthio)carbonothioyl) piperazine-1-carboxylate (35): Yield 81.1%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 8.23 (d, J = 8.8 Hz, 2H), 7.70 (s, 1H), 7.41 (d, J = 8.8 Hz, 2H), 5.61 (s, 2H), 4.70 (s, 2H), 4.29 (brs, 2H), 3.91 (brs, 2H), 3.55 (t, J = 5.3 Hz, 4H), 1.47 (s, 9H); 13 C 2 MR (101 MHz, CDCl 3 ) δ , , , , , , , , 80.69, 53.08, 31.58, 28.34; HRM (EI) calcd for C 20 H 26 6 a 4 2 [M + a] + : , found: tert Butyl4-(((1-(3-hydroxybenzyl)-1H-1,2,3-triazol-4-yl)methylthio)carbonothioyl) piperazine-1-carboxylate (36): Yield 72.8%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ (s, 1H), 7.64 (s, 1H), (m, 5H), 5.49 (s, 2H), 4.62 (s, 2H), 4.30 (brs, 2H), 3.87 (brs, 2H), 3.51 (s, 4H), 1.48 (s, 9H); HRM (EI) calcd for C 20 H 27 5 a 3 2 [M + a] + : , found: tert Butyl 4-(((1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)methylthio)carbonothioyl) -piperazine-1-carboxylate (38): Cl H Cl Yield 90.2%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.64 (s, 1H), 7.43 (d, J = 8.2 Hz, 1H), 7.35 (d, J = 2.0 Hz, 1H), 7.08 (dd, J 1 = 2.0 Hz, J 2 = 8.2 Hz, 1H), 5.44 (s, 2H), 4.70 (s, 2H), 4.30 (brs, 2H), 3.91 (brs, 2H), 3.52 (t, J = 5.1 Hz, 4H), 1.47 (s, 9H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , , , 80.65, 52.82, 31.65, 28.34; HRM (EI) calcd for C 20 H 26 Cl [M + H] + : , found: tert Butyl 4-(((1-(2,6-difluorobenzyl)-1H-1,2,3-triazol-4-yl) methylthio) carbonthioy)- piperazine-1- carboxylate (39): Yield 77.8%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.71 (brs, 1H), (m, 1H), (m, 2H), 5.58 (s, 2H), 4.67 (s, 2H), 4.30 (brs, 2H), 3.91 (brs, 2H), 3.53 (s, 4H), 1.47 (s, 9H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , , , , , , , , , 80.62, 41.39, 31.85, 28.35; HRM (EI) calcd for C 20 H [M + H] + : , found: tert Butyl 4-(((1-p-tolyl-1H-1,2,3-triazol-4-yl)methylthio) carbonothioyl) piperazine -1- carboxylate (41): Yield 78.4%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 8.08 (s, 1H), 7.59 (d, J = 8.4 Hz, 2H), 7.30 (d, J = 8.4 Hz, 2H), 4.79 (s, 2H), 4.32 (brs, 2H), 3.93 (brs, 2H), 3.56 (t, J = 5.2 Hz, 4H), 2.41 (s, 3H), 1.47 (s, 9H); 13 C MR (100 MHz, DM-d 6, ppm): δ , , , , , , 80.62, 31.71, 28.35, 21.09; HRM (EI) calcd 5
6 for C 20 H [M + H] + : , found: tert Butyl 4-(((1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methylthio)carbonthioyl)- piperazine-1-carboxylate (42): H 3 C Yield 83.0%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 8.04 (s, 1H), 7.61 (d, J = 9.0 Hz, 2H), 7.01 (d, J = 9.0 Hz, 2H), 4.79 (s, 2H), 4.32 (brs, 2H), 3.94 (brs, 2H), 3.86 (s, 3H), 3.56 (t, J = 5.3 Hz, 4H), 1.47 (s, 9H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , 80.64, 55.63, 31.72, 28.35; HRM (EI) calcd for C 20 H [M + H] + : , found: tert Butyl 4-(((1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylthio) carbonthioyl)- piperazine-1-carboxylate (43): Yield 77.5%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 8.09 (s, 1H), (m, 4H), 4.79 (s, 2H), 4.32 (brs, 2H), 3.93 (brs, 2H), 3.56 (t, J = 5.2 Hz, 4H), 1.47 (s, 9H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , , 80.67, 31.56, 28.35; HRM (EI) calcd for C 19 H [M + H] + : , found: tert Butyl 4-(((1-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-yl)methylthio)- carbonothioyl) piperazine-1-carboxylate (44): 3 C Yield 87.6%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 8.21 (s, 1H), 8.01 (s, 1H), 7.96 (d, J = 7.6 Hz, 1H), (m, 2H), 4.82 (s, 2H), 4.34 (brs, 2H), 3.95 (brs, 2H), 3.57 (t, J =5.2 Hz, 4H), 1.48 (s, 9H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , , , , , , , , , , , , , ,117.42, , 80.67, 31.45, 28.33; HRM (EI) calcd for C 20 H [M + H] + : , found: tert Butyl 4-(((1-(4-methylphenethyl)-1H-1,2,3-triazol-4-yl)methylthio)carbonothioyl) piperazine-1-carboxylate(45): H 3C Yield 79.1%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.47 (s, 1H), 7.13 (d, J = 7.8 Hz, 2H), 7.02 (d, J = 7.8 Hz, 2H), 4.69 (s, 2H), 4.55 (t, J = 7.3 Hz, 2H), 4.33 (brs, 2H), 3.94 (brs, 2H), 3.57 (t, J =5.1 Hz, 4H), 3.18 (t, J = 7.2 Hz, 2H), 2.35 (s, 3H), 1.49 (s, 9H); 13 C MR (100 MHz, CDCl 3, ppm): δ196.51, , , , , , , , 80.66, 51.78, 36.34, 31.81, 28.36, 21.10; HRM (EI) calcd for C 22 H 31 5 a 2 2 [M + a] + : , found: tert Butyl 4-(((1-(2-fluorophenethyl)-1H-1,2,3-triazol-4-yl)methylthio) carbonothio yl)piperazine-1-carboxylate (46): Yield 69.0%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl3, ppm): δ 7.49 (s, 1H), (m, 4H), 4.67 (s, 2H), 4.58 (t, J = 7.3 Hz, 2H), 4.33 (brs, 2H), 3.92 (brs, 2H), 3.57 (t, J = 5.2 Hz, 4H), 3.26 (t, J = 7.3 Hz, 2H), 1.48 (s, 9H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , , , 6
7 123.89, , , , 80.66, 50.05, 31.75, 30.61, 30.59, 28.36; HRM (EI) calcd for C 21 H 28 5 a 2 2 [M + a] + : , found: tert Butyl 4-(((1-(naphthalen-2-ylmethyl)-1H-1,2,3-triazol-4-yl)methylthio) carbonthioyl)piperazine-1-carboxylate (48): Yield 82.0%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ (m, 4H), 7.76 (s, 1H), (m, 2H), 7.38 (dd, J 1 = 1.2 Hz, J 2 = 8.4 Hz, 1H), 5.67 (s, 2H), 4.71 (s, 2H), 4.31 (brs, 2H), 3.92 (brs, 2H), 3.54 (s, 4H), 1.49 (s, 9H); 13 C MR (100 MHz, CDCl 3, ppm): δ196.42, , , , , , , , , , , 80.63, 54.41, 31.88, 28.36; HRM (EI) calcd for C 24 H [M + H] + : , found: tert Butyl 4-(((1-((2-oxo-1,2-dihydroquinolin-4-yl)methyl)-1H-1,2,3-triazol-4-yl) methylthio)carbonothioyl)piperazine-1-carboxylate(49): H Yield 79.8%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ (s, 1H), 8.24 (s, 1H), 7.83 (d, J = 5.0 Hz, 1H), 7.55 (s, 1H), 7.36 (dd, J 1 = 3.2 Hz, J 2 = 5.0 Hz, 1H), 7.23 (d, J = 3.2 Hz, 1H), 5.95 (s, 1H), 5.92 (s, 2H), 4.62 (s, 2H), 4.32 (brs, 2H), 3.92 (brs, 2H), 3.46 (s, 4H), 1.42 (s, 9H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , , , , , 79.88, 50.12, 31.83, 28.48; HRM (EI) calcd for C 23 H 28 6 a 3 2 [M + a] + : , found: tert Butyl 4-(((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl) methylthio)carbonothioyl)piperazine-1-carboxylate (50): Yield 84.7%, white solid. Mp: o C; 1 H MR (400 MHz, H CDCl 3, ppm): δ 7.88 (s, 1H), 7.63 (dd, J 1 = 3.1 Hz, J 2 = 6.0 Hz, 2H), 7.30 (dd, J 1 = 3.1 Hz, J 2 = 6.0 Hz, 2H), 5.84 (s, 2H), 4.68 (s, 2H), 4.25 (brs, 2H), 3.83 (brs, 2H), 3.49 (s, 4H), 1.46 (s, 9H); MR (100 MHz, CDCl 3, ppm): δ , , , , , , 80.68, 48.41, 31.48, 28.35; HRM (EI) calcd for C 24 H [M + H] + : , found: tert Butyl 4-(((1-((5-oxo-2,5-dihydrofuran-3-yl)methyl)-1H-1,2,3-triazol-4-yl) methylthio)carbonothioyl)piperazine-1-carboxylate (51): Yield 74%,white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 8.11 (s, 1H), 5.84 (s, 2H), 5.65 (s, 1H), 4.96 (s, 2H), 4.69 (s, 2H), 4.30 (brs, 2H), 3.99 (brs, 2H), 3.76 (s, J = 4.9 Hz, 4H), 1.47 (s, 9H); HRM (EI) calcd for C 18 H 25 5 a 4 2 [M + a] + : , found: (1-(4-Methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl4-methylpiperazine-1-carbodithioae (54): Yield 90.1%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.57 (s, 1H), 7.16 (s, 4H), 5.43 (s, 2H), 4.67 (s, 2H), 4.33 (brs, 2H), 3.91 (brs, 2H), 2.47 (s, 4H), 2.34 (s, 3H), 2.31 (s, 3H); 13 C MR (100 MHz, CDCl 3 ) δ , , , , , , , 54.34, 53.93, 45.60, 31.89, 7
8 21.17; HRM (EI) calcd for C 17 H 23 5 a 2 [M + a] + : , found: (1-(4-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl methylpiperazine-1-carbodithioate (55): Yield 87.4%, white solid. Mp: o C; 1 H MR (400 MHz, Acetone) δ 8.00 (s, 1H), (m, 2H), (m, 2H), 5.63 (s, 2H), 4.63 (s, 2H), 4.30 (brs, 2H), 3.92 (brs, 2H), 2.45 (s, 4H), 2.28 (s, 3H); HRM (EI) calcd for C 16 H 20 5 a 2 [M + a] + : , found: (1-(4-Methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl4-benzylpiperazine-1-carbodithioate (59): Yield 84%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.68 (s, 1H), (m, 9H), 5.54 (s, 2H), 4.69 (s, 2H), 4.34 (brs, 2H), 3.91 (brs, 2H), 3.53 (s, 2H), 2.52 (s, 4H), 2.30 (s, 3H); 13 C MR (100 MHz, CDCl 3, ppm): δ 196.4, 154.5, 136.8, 132.5, 131.1, 129.3, 129.1, 126.7, , , , , , , , 62.46, 52.35, 47.64, 47.60, 31.83, 28.44; HRM (EI) calcd for C 23 H 27 5 a 2 [M + a] + : , found: (1-(4-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl4-benzylpiperazine-1-carbodithioate (60): Yield 81.0%, white solid. Mp: o C. 1 H MR (400 MHz, CDCl 3, δ, ppm): 7.67 (s, 1H), (m, 9H), 5.54 (s, 2H), 4.68 (s, 2H), 4.34 (brs, 2H), 3.90 (brs, 2H), 3.53 (s, 2H), 2.52 (s, 4H); 13 C MR (100 MHz, CDCl 3, δ, ppm): , , , , , , , , , , , , , , , , , , , 62.46, 52.35, 47.64, 47.60, 31.83; HRM (EI) calcd for C 22 H 24 5 a 2 [M + a] + : , found: (1-(4-Methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-(2-hydroxyethyl)piperazine-1- carbodithioate (61): Yield 85.8%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.58 (s, 1H), 7.18 (s, 4H), 5.46 (s, 2H), 4.69 (s, 2H), 4.36 (brs, 2H), 3.94 (brs, 2H), 3.69 (t, J = 5.3 Hz, 2H), 2.62 (t, J = 5.3 Hz, 6H), 2.37 (s, 3H); 13 C MR (101 MHz, CDCl 3 ) δ , , , , , , , 59.09, 58.00, 53.95, 52.33, 31.89, 21.17; HRM (EI) calcd for C 18 H [M + H] + : , found: (1-(2-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-(2-hydroxyethyl)piperazine-1- carbodithioate (62): H H Yield 71.0%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.69 (s, 1H), (m, 1H), (m, 3H), 5.57 (s, 2H), 4.70 (s, 2H), 4.37 (brs, 2H), 3.95 (brs, 2H), 3.69 (t, J = 5.3 Hz, 2H), 2.62 (t, J = 5.3 Hz, 6H); 13 C MR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , 59.06, 57.98, 52.32, 47.66, 47.62, 31.84; HRM (EI) calcd for C 17 H [M + H] + : , found:
9 (1-(4-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-(2-hydroxyethyl)piperazine-1- carbodithioate (63): Yield 75.9%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.69 (s, 1H), (m, 1H), (m, 3H), 5.57 (s, 2H), 4.70 (s, 2H), 4.37 (brs, 2H), 3.95 (brs, 2H), 3.69 (t, J = 5.3 Hz, 2H), 2.62 (t, J = 5.3 Hz, 6H); HRM (EI) calcd for C 17 H [M + H] + : , found: (1-(4-Methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-phenylpiperazine-1- carbodithioate (64): Yield 72.4%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.59 (s, 1H), (m, 2H), (m, 4H), (m, 3H), 5.46 (s, 2H), 4.72 (s, 2H), 4.49 (brs, 2H), 4.11 (brs, 2H), 3.32 (t, J = 4.8 Hz, 4H), 2.37 (s, 3H); HRM (EI) calcd for C 22 H 25 5 a 2 [M + a] + : , found: (1-(2-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl4-phenylpiperazine-1-carbodithioate (65): Yield 89.3%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.70 (s, 1H), (m, 4H), (m, 2H), (m, 3H), 5.57 (s, 2H), 4.73 (s, 2H), 4.49 (brs, 2H), 4.09 (brs, 2H), 3.30 (t, J = 4.9 Hz, 4H); HRM (EI) calcd for C 21 H 22 5 a 2 [M + a] + : , found: (1-(4-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-phenylpiperazine-1-carbodithioate (66): Yield 77.7%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.62 (s, 1H), (m, 4H), (m, 2H), (m, 3H), 5.48 (s, 2H), 4.73 (s, 2H), 4.50 (brs, 2H), 4.09 (brs, 2H), 3.32 (t, J = 4.9 Hz, 4H); HRM (EI) calcd for C 21 H [M + H] + : , found: (1-(4-Methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-(pyrimidin-2-yl)piperazine-1- carbodithioate (67): Yield 81.1%, white solid. Mp: o C; 1 H MR (400 MHz, H 3 C C 20 H [M + H] + : , found: H CDCl 3 ) δ 8.35 (d, J = 4.8 Hz, 2H), 7.59 (s, 1H), 7.18 (s, 4H), 6.59 (t, J = 4.8 Hz, 1H), 5.45 (s, 2H), 4.71 (s, 2H), 4.41 (brs, 2H), 4.00 (brs, 2H), 3.95 (t, J = 3.2 Hz, 4H), 2.35 (s, 3H); 13 C MR (101 MHz, CDCl 3 ) δ , , , , , , , , 53.97, 42.93, 31.87, 21.16; HRM (EI) calcd for (1-(2-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-(pyrimidin-2-yl)piperazine-1- carbodithioate (68 ): 9
10 Yield 80.3%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 8.36 (d, J = 4.8 Hz, 2H), 7.70 (s, 1H), (m, 1H), (m, 1H), (m, 2H), 6.60 (t, J = 4.8 Hz, 1H), 5.57 (s, 2H), 4.74 (s, 2H), 4.43 (brs, 2H), 4.02 (brs, 2H), 3.97 (t, J = 3.2 Hz, 4H); HRM (EI) calcd for C 19 H 20 7 a 2 [M + a] + : , found: (1-(4-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-(pyrimidin-2-yl)piperazine-1- carbodithioate (69): Yield 83.4%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 8.36 (d, J = 4.8 Hz, 2H), 7.62 (s, 1H), (m, 2H), (m, 2H), 6.60 (t, J = 4.8 Hz, 1H), 5.48 (s, 2H), 4.73 (s, 2H), 4.42 (brs, 2H), 4.03 (brs, 2H), 3.96 (t, J = 3.2 Hz, 4H); HRM (EI) calcd for C 19 H 20 7 a 2 [M + a] + : , (1-(4-Methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-(methylsulfonyl)piperazine-1- carbodithioate (70): H 3 C found: Yield 91.2%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.55 (s, 1H), 7.19 (s, 4H), 5.46 (s, 2H), 4.67 (s, 2H), 4.25 (brs, 4H), 3.34 (t, J = 5.0 Hz, 4H), 2.82 (s, 3H), 2.37 (s, 3H); HRM (EI) calcd for C 17 H 23 5 a 2 3 [M + a] + : , found: (1-(2-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-(methylsulfonyl)piperazine-1- carbodithioate (71) Yield 88.5%, white solid. Mp: o C. 1 H MR (400 MHz, CDCl 3 ) δ 7.67 (s, 1H), (m, 1H), (m, 1H), (m, 2H), 5.57 (s, 2H), 4.69 (s, 2H), 4.30 (brs, 2H), 4.17 (brs, 2H), 3.35 (t, J = 5.1 Hz, 4H), 2.82 (s, 3H); HRM (EI) calcd for C 16 H 20 5 a 2 3 [M + a] + : , found: (1-(4-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-(methylsulfonyl)piperazine-1- carbodithioate (72) Yield 89.0%, white solid. Mp: o C. 1 H MR (400 MHz, C 16 H 20 5 a 2 3 [M + a] + : , found: CDCl 3 ) δ 7.58 (s, 1H), (m, 2H), (m, 2H), 5.47 (s, 2H), 4.67 (s, 2H), 4.27 (brs, 4H), 3.34 (t, J = 5.0 Hz, 4H), 2.82 (s, 3H); 13 C MR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , 53.42, 45.23, 35.15, 32.03; HRM (EI) calcd for (1-(4-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl piperazine-1-carbodithioate (74): Yield 93.9%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.60 (s, 1H), (m, 4H), 5.45 (s, 2H), H 4.69 (s, 2H), 4.31 (brs, 2H), 3.89 (brs, 2H), 2.93 (s, 4H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , , , , 53.41, 45.15, 31.76; HRM (EI) calcd for C 15 H [M + H] + : , found: (1-(2-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)methyl piperazine-1-carbodithioate (75): 10
11 Yield 94.8%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.68 (s, 1H), 7.43 (dd, J 1 = 1.4 Hz, J 2 = 7.8 Hz, 1H), H 7.33 (m, 2H), 7.18 (dd, J 1 = 1.6 Hz, J 2 = 7.4 Hz, 1H), 5.61 (s, 2H), Cl 4.64 (s, 2H), 4.45 (brs, 4H), 3.34 (s, 4H); 13 C MR (100 MHz, CDCl 3, δ, ppm): , , , , , , , , , 51.57, 43.19, 32.18; HRM (EI) calcd for C 15 H 19 Cl 5 2 [M + H] + : , found: (1-(4-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)methyl piperazine-1-carbodithioate (76): Yield 95.1%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.61 (s, 1H), 7.35 (d, J = 8.1 Hz, 2H), 7.20 (d, 2H, H J = 8.1 Hz), 5.45 (s, 2H), 4.69 (s, 2H), 4.31 (brs, 2H), 3.90 (brs, Cl 2H), 2.94 (s, 4H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , 53.36, 45.61, 31.65; HRM (EI) calcd for C 15 H 19 Cl 5 2 [M + H] + : , found: (1-(3,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl)methylpiperazine-1-carbodithioate (81): Yield 95.5%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.65 (s, 1H), 7.45 (d, J = 8.3 Hz, 1H), 7.35 (d, J = H 2.0 Hz, 1H), 7.10 (dd, J 1 = 2.0 Hz, J 2 = 8.3 Hz, 1H), 5.44 (s, 2H), Cl 4.70 (s, 2H), 4.31 (brs, 2H), 3.92 (brs, 2H), 2.95 (s, 4H); 13 Cl C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , , 52.81, 45.63, 31.56; HRM (EI) calcd for C 15 H 18 Cl [M + H] + : , found: Benzyl 4-(((1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl)methylthio) carbonothioyl) piperazine-1-carboxylate (85): Cl Yield 71.7%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3, ppm): δ 7.67 (s, 1H), (m, 9H), 5.61 (s, 2H), 5.15 (s, 2H), 4.69 (s, 2H), 4.28 (brs, 2H), 3.95 (brs, 2H), 3.61 (t, J = 5.3 Hz, 4H); 13 C MR (100 MHz, CDCl 3, ppm): δ , , , , , , , , , , , , , , 67.65, 51.40, 43.04, 31.89; HRM (EI) calcd for C 23 H 25 Cl [M + H] + : , found: (1-(4-luorobenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-acetylpiperazine-1-carbodithioate (94): Yield 81.1%, white solid. Mp: o C. 1 H MR (400 MHz, DM-d 6 ) δ 8.14 (s, 1H), (m, 2H), (m, 2H), 5.56 (s, 2H), 4.59 (s, 2H), 4.27 (brs, 2H), 3.90 (brs, 2H), 3.59 (t, J = 4.9 Hz, 4H), 2.03 (s, 3H); HRM (EI) calcd for C 17 H [M + H] + : , found: (1-(4-Methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl 4-acetylpiperazine-1-carbodithioate (95): H 3 C Yield 76.2%, white solid. Mp: o C; 1 H MR (400 MHz, CDCl 3 ) δ 7.57 (s, 1H), 7.17 (s, 4H), 5.44 (s, 2H), 4.67 (s, 2H), 4.30 (brs, 2H), 3.99 (brs, 2H), 3.74 (t, J = 5.6 Hz, 2H), 3.60 (t, J = 5.6 Hz, 2H), 2.36 (s, 3H), 2.13 (s, 3H); 13 C MR (101 MHz, CDCl 3 ) δ , , , , , , 53.99, 45.16, 11
12 40.56, 31.96, 21.36, 21.16; HRM (EI) calcd for C 18 H [M + H] + : , found:
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Supporting Information. Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors
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Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process
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Supporting Information for An atom-economic route to densely functionalized thiophenes via base-catalyzed rearrangement of 5-propargyl-2H-thiopyran-4(3H)-ones Chunlin Tang a, Jian Qin b, Xingqi Li *a a
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Supporting Information Structure-Activity and Structure-Property Relationship and Exploratory in vivo Evaluation of the Nanomolar Keap1-Nrf2 Protein-Protein Interaction Inhibitor Zheng-Yu Jiang, a,b Li-Li
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Supporting Information. for. A novel application of 2-silylated 1,3-dithiolanes for the. synthesis of aryl/hetaryl-substituted ethenes and
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Supporting Information for Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction Chun-Huan Jiang, Xiantao Lei,
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Electronic Supplementary Information Unprecedented Carbon-Carbon Bond Cleavage in Nucleophilic Aziridine Ring Opening Reaction, Efficient Ring Transformation of Aziridines to Imidazolidin-4-ones Jin-Yuan
Discovery of multi-target receptor tyrosine kinase inhibitors as novel anti-angiogenesis agents
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Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 A new route to enantiopure b-aryl-substituted b-amino acids and 4-aryl-substituted b-lactams through lipase-catalyzed
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Supporting Information for Palladium-Catalyzed C-H Bond Functionalization of C6-Arylpurines Hai-Ming Guo,* Wei-Hao Rao, Hong-Ying iu, Li-Li Jiang, Ge ng, Jia-Jia Jin, Xi-ing Yang, and Gui-Rong Qu* College
Supplementary Data. Engineering, Nanjing University, Nanjing , P. R. China;
Supplementary Data Synthesis, Chemo-selective Properties of Substituted 9-Aryl-9H-fluorenes from Triarylcarbinols and Enantiomerical Kinetics of Chiral 9-Methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene
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Supporting Information 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions
Zuxiao Zhang, Xiaojun Tang and William R. Dolbier, Jr.* Department of Chemistry, University of Florida, Gainesville, FL
Photoredox-Catalyzed Intramolecular Difluoromethylation of -Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H Containing 2- Azaspiro[4.5]deca-6,9-diene-3,8-diones. Zuxiao
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Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%. S1 Supplementary Figure S2. Single X-ray structure 5a at probability ellipsoids of 20%. S2 H 15 Ph Ac Ac I AcH Ph Ac
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Supplementary Information for Organocatalytic Asymmetric Intramolecular [3+2] Cycloaddition: A Straightforward Approach to Access Multiply Substituted Hexahydrochromeno[4,3-b]pyrrolidine Derivatives in
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Supporting Information Table of Contents 1. General remarks...s1 2. Synthesis of catalyst L S1
Diastereo- and Enantioselective Conjugate Addition of 3-Substituted xindoles to itroolefins Catalyzed by a Chiral i(ac) 2 -Diamine Complex under Mild Conditions Yan-Yan Han,, Zhi-Jun Wu, Wen-Bing Chen,,
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Supporting Information Gold-catalyzed Cycloisomerization of 1,6-Diyne-4-en-3-ols to form Naphthyl Ketone Derivatives. Jian-Jou Lian and Rai-Shung Liu* Department of Chemistry, National Tsing-Hua University,
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SUPPLEMENTARY MATERIAL. A Facile and Convenient Approach for the Synthesis of Novel Sesamol-Oxazine and Quinoline- Oxazine Hybrids
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Supporting Information for A ovel Synthesis of luorinated Pyrazoles via Gold(I)-Catalyzed Tandem Aminofluorination of Alkynes in the Presence of Selectfluor Jianqiang Qian, Yunkui Liu,* Jie Zhu, Bo Jiang,
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Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Electronic Supplementary Information (ESI) For Iron-Catalysed xidative Amidation of Alcohols with Amines Silvia Gaspa, a Andrea
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Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2014 A Family of Click Nucleosides for Metal-Mediated Base Pairing: Unravelling the Principles of Highly Stabilizing Metal-Mediated
National d Histoire Naturelle, 57 rue Cuvier (C.P. 54), Paris, France. Contents:
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Supporting Information Selective Synthesis of xygen-containing Heterocycles via Tandem Reactions of 1,2-Allenic Ketones with Ethyl 4-Chloroacetoacetate Qiang Wang, a, b Zhouqing Xu b and Xuesen Fan a *
Available online at
J. Serb. Chem. Soc. 76 (12) S1 S5 (2011) Supplementary material SUPPLEMENTARY MATERIAL TO Synthesis of quinoline-attached furan-2(3h)-ones having anti-inflammatory and antibacterial properties with reduced
Supporting Information One-Pot Approach to Chiral Chromenes via Enantioselective Organocatalytic Domino Oxa-Michael-Aldol Reaction
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and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol
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