Activity

Matched Antibody Pairs ; yield 75 ; 1H NMR (400 MHz, DMSO-d6) 10.23 (s, 1H), 8.33 (d, J = 13.2 Hz, 1H), 7.92 (dd, J = 13.2, 0.8 Hz, 1H), 7.64 (s, 4H), 7.53 (d, J = 16.0 Hz, 1H), 7.09 (d, J = 16.0 Hz, 1H), 6.89 (s, 1H), 6.67 (s, 1H), 4.67 (s, 2H), 3.97 (s, 3H), 3.92 (s, 3H), 2.14 (s, 3H). 13C NMR (101 MHz, DMSO-d6) 170.55, 166.03, 163.90, 162.33, 144.02, 139.11, 137.46, 134.54, 133.06, 132.28, 128.16 (2C), 124.63, 119.79 (2C), 109.97, 105.58, 98.43, 63.02, 56.72, 56.27, 20.95. HRMS (ESI): m/z [M + H]+ calcd for C22H22N2O7: 427.15; found: 427.1491. 4.9.11. 2-Chloro-N-(4-((E)-3,5-dimethoxy-2-((E)-2-nitrovinyl)styryl)phenyl)acetamide (43). Yellow solid; yield 15 ; 1H NMR (400 MHz, DMSO-d6) 10.46 (s, 1H), 8.33 (d, J = 13.2 Hz, 1H), 7.pubs.acs.org/jmcArticle(d, J = 13.2 Hz, 1H), 7.66 (s, 4H), 7.55 (d, J = 16.0 Hz, 1H), 7.10 (d, J = 16.0 Hz, 1H), 6.90 (d, J = 2.4 Hz, 1H), 6.67 (d, J = 2.4 Hz, 1H), 4.29 (s, 2H), 3.97 (s, 3H), 3.92 (s, 3H). 13C NMR (100 MHz, CDCl3) 165.15, 163.88, 162.32, 143.94, 139.12, 137.44, 134.44, 133.01, 132.56, 128.16 (2C), 124.77, 119.86, 109.97, 105.57, 98.41, 56.70, 56.25, 49.06, 44.08; HRMS (ESI): m/z [M + H]+ calcd for C20H19ClN2O5: 403.1055; found: 403.1054. 4.9.12. 3-Chloro-N-(4-((E)-3,5-dimethoxy-2-((E)-2-nitrovinyl)styryl)phenyl)propanamide (44). Tag Antibodies ; yield 25 ; 1H NMR (400 MHz, DMSO-d6) 10.30 (s, 1H), 8.34 (d, J = 13.3 Hz, 1H), 7.93 (d, J = 13.2 Hz, 1H), 7.74 (d, J = 8.7 Hz, 2H), 7.66 (d, J = 8.6 Hz, 2H), 7.55 (d, J = 16.0 Hz, 1H), 7.10 (d, J = 16.0 Hz, 1H), 6.90 (d, J = 2.1 Hz, 1H), 6.68 (d, J = 2.0 Hz, 1H), 6.46 (dd, J = 17.0, 10.1 Hz, 1H), 6.28 (dd, J = 17.0, 2.0 Hz, 1H), 5.79 (dd, J = 10.1, 2.0 Hz, 1H), 3.97 (s, 3H), 3.92 (s, 3H). 13C NMR (101 MHz, DMSO-d6) 163.90, 163.63, 162.34, 144.03, 139.71, 137.48, 134.60, 133.06, 132.23, 128.16, 127.61, 124.59, 119.86, 109.97, 105.58, 98.43, 56.74, 56.28. HRMS (ESI): m/z [M + H]+ calcd for C21H21ClN2O5: 417.1211; found: 417.1212. 4.9.13. N-(4-((E)-3,5-Dimethoxy-2-((E)-2-nitrovinyl)styryl)phenyl)acrylamide (45). Yellow solid; yield 20 ; 1H NMR (400 MHz, DMSO-d6) 10.30 (s, 1H), 8.34 (d, J = 13.3 Hz, 1H), 7.93 (d, J = 13.2 Hz, 1H), 7.77-7.60 (m, 4H), 7.55 (d, J = 16.0 Hz, 1H), 7.10 (d, J = 16.0 Hz, 1H), 6.90 (d, J = 2.4 Hz, 1H), 6.68 (d, J = 2.4 Hz, 1H), 6.46 (dd, J = 17.0, 10.0 Hz, 1H), 6.28 (dd, J = 17.0, 2.0 Hz, 1H), 5.79 (dd, J = 10.0, 2.0 Hz, 1H), 3.97 (s, 3H), 3.92 (s, 3H). 13C NMR (100 MHz, CDCl3) 163.90, 163.63, 162.34, 144.02, 139.71, 137.47, 134.59, 133.06, 132.26, 128.15 (2C), 127.60, 124.58, 119.86 (2C), 119.58, 105.57, 98.42, 56.73, 56.27; HRMS (ESI): m/z [M + H]+ calcd for C21H20N2O5: 381.1445; found: 381.1419. 4.9.14. (E)-N-(4-((E)-3,5-Dimethoxy-2-((E)-2-nitrovinyl)styryl)phenyl)but-2-enamide (46). Yellow solid; yield 20 ; 1H NMR (400 MHz, DMSO-d6) 10.10 (s, 1H), 8.34 (d, J = 13.2 Hz, 1H), 7.93 (d, J = 13.2 Hz, 1H), 7.71 (d, J = 8.8 Hz, 2H), 7.63 (d, J = 8.8 Hz, 2H), 7.53 (d, J = 16.0 Hz, 1H), 7.09 (d, J = 16.0 Hz, 1H), 6.89 (d, J = 2.0 Hz, 1H), 6.82 (dq, J = 13.6, 6.8 Hz, 1H), 6.67 (d, J = 2.0 Hz, 1H), 6.15 (dd, J = 15.2, 2.0 Hz, 1H), 3.97 (s, 3H), 3.92 (s, 3H), 1.88 (dd, J = 6.8, 1.6 Hz, 3H). 13C NMR (100 MHz, CDCl3) 163.96, 163.90, 162.34, 144.06, 140.63, 140.03, 137.46, 134.66, 133.06, 131.93, 128.10 (2C), 126.37, 124.38, 119.73 (2C), 109.96, 105.54, 98.39, 56.72, 56.26, 18.03; HRMS (ESI): m/z [M + H]+ calcd for C22H22N2O5: 395.1601; found: 395.1602. 4.9.15. N-(4-((E)-3,5-Dimethoxy-2-((E)-2-Nitrovinyl)styryl)phenyl)cyclopropanecarboxamide (47.