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25.54, 28.22, 120.25, 120.79, 126.39, 126.59, 128.81, 129.30, 131.85,
133.01, 137.49, 141.03, 169.94, 171.20. Anal. Calc. for C18H18N2O2: C,
73.45%; H, 6.16%; N, 9.52%. Found: C, 73.70%; H, 6.21%; N, 9.15%.
with D2O). 13C-NMR (
d) (DMSO) 20.85, 119.52, 120.44, 127.37,
127.54, 128.03, 128.66, 129.50, 132.14, 133.47, 133.89, 138.17, 139.39,
143.87, 164.25, 171.72. Anal. Calc. for C21H18N2O2: C, 76.34%; H,
5.49%; N, 8.48%. Found: C, 76.22%; H, 5.26%; N, 8.18%.
4.1.7.5. 5-Methoxy-2-((1R,2R)-2-phenylcyclopropane-1-
carboxamido)benzamide (13e). 13% yield; mp 197e200 ꢀC
(ethanol); I.R. (KBr) cm-1 3361, 3305, 3179 (NH, NH2), 1655, 1618 (2
4.1.7.11. N-(2-carbamoyl-4-methoxyphenyl)-[1,1'-biphenyl]-4-
carboxamide (14e). 55% yield; mp 242e244 ꢀC (ethanol); I.R. (KBr)
cm-1 3356, 3245, 3186 (NH, NH2), 1655, 1645 (broad, 2 CO) 1H-NMR
CO) 1H-NMR (DMSO)
d 1.35e1.37 (m, 1H, cyclopropane CH-H);
1.47e1.51 (m, 1H, cyclopropane CH-H); 1.91e1.94 (m, 1H, cyclo-
propane CH); 2.39e2.42 (m, 1H, cyclopropane CH); 3.33 (s, 3H,
OCH3); 7.06e8.33 (set of signals, 10H, aromatic protons and
exchangeable NH2); 11.52 (s, 1H, NH; exchangeable with D2O). 13C-
(DMSO)
protons and exchangeable NH2); 12.74 (s, 1H, NH; exchangeable
with D2O). 13C-NMR (
) (DMSO) 55.51,113.58,118.09,120.59,121.65,
126.89, 127.05, 127.50, 128.17, 129.03, 133.34, 133.48, 138.94, 143.30,
154.32, 163.56, 170.83. Anal. Calc. for C21H18N2O3: C, 72.82%; H,
5.24%; N, 8.09%. Found: C, 73.15%; H, 5.55%; N, 8.16%.
d 3.86 (s, 3H, OCH3); 7.21e8.69 (set of signals,14H, aromatic
d
NMR (d) (DMSO) 16.08, 24.83, 27.48, 55.33, 113.16, 117.52, 121.15,
122.18, 125.84, 126.01, 128.25, 132.44, 140.55, 154.07, 169.18, 170.17.
Anal. Calc. for C18H18N2O3: C, 69.66%; H, 5.85%; N, 9.03%. Found: C,
69.99%; H, 6.23%; N, 9.32%.
4.1.7.12. N-(2-carbamoyl-4,5-dimethoxyphenyl)-[1,1'-biphenyl]-4-
carboxamide (14f). 53% yield; mp 230e232 ꢀC (ethanol); I.R. (KBr)
cm-1 3356, 3245, 3186 (NH, NH2), 1655, 1645 (broad, 2 CO) 1H-NMR
4.1.7.6. 4,5-Dimethoxy-2-((1R,2R)-2-phenylcyclopropane-1-
carboxamido)benzamide (13f). 21% yield; mp 200e203 ꢀC
(ethanol); I.R. (KBr) cm-1 3420, 3299, 3203 (NH, NH2), 1659, 1641 (2
(DMSO)
signals, 13H, aromatic protons and exchangeable NH2); 13.43 (s, 1H,
NH; exchangeable with D2O). 13C-NMR (
) (DMSO) 55.45, 55.98,
d 3.84 (s, 3H, OCH3); 3.87 (s, 3H, OCH3); 7.43e8.57 (set of
CO) 1H-NMR (DMSO)
d
1.34e1.41 (m, 1H, cyclopropane CH-H);
d
1.51e1.55 (m, 1H, cyclopropane CH-H); 1.84e1.89 (m, 1H, cyclo-
propane CH); 2.38e2.46 (m, 1H, cyclopropane CH); 3.46 (s, 6H, 2
OCH3); 7.18e8.29 (set of signals, 9H, aromatic protons and
exchangeable NH2); 12.36 (s, 1H, NH; exchangeable with D2O). 13C-
103.93, 110.06, 111.76, 126.90, 127.08, 127.52, 128.19, 129.03, 133.51,
135.87, 138.92, 143.37, 143.60, 151.65, 163.76, 171.01. Anal. Calc. for
C22H20N2O4: C, 70.20%; H, 5.36%; N, 7.44%. Found: C, 69.80%; H,
5.27%; N, 7.35%.
NMR (d) (DMSO) 16.59, 25.22, 28.53, 55.80, 56.35, 103.95, 110.46,
112.01, 126.40, 126.61, 128.82, 135.88, 141.00, 143.75, 151.93, 169.88,
171.04. Anal. Calc. for C19H20N2O4: C, 67.05%; H, 5.92%; N, 8.23%.
Found: C, 67.07%; H, 6.19%; N, 7.88%.
4.1.7.13. N-(2-carbamoylphenyl)-[1,1'-biphenyl]-2-carboxamide
(17a). 28% yield; mp 155e163 ꢀC (ethanol); I.R. (KBr) cm-1 3375,
3197-2960 (NH, NH2), 1668, 1622 (2 CO) 1H-NMR (DMSO)
d
7.09e8.49 (set of signals, 15H, aromatic protons and exchangeable
4.1.7.7. N-(2-carbamoylphenyl)-[1,1'-biphenyl]-4-carboxamide
(14a). 45% yield; mp 225e230 ꢀC (ethanol); I.R. (KBr) cm-1 3376,
3206, 3189 (NH, NH2), 1654, 1633 (2 CO) 1H-NMR (DMSO)
NH2); 11.94 (s, 1H, NH; exchangeable with D2O). 13C-NMR (
d)
(DMSO) 119.64, 120.00, 122.68, 127.34, 127.56, 127.74, 128.28,
128.36, 128.56, 130.34, 130.41, 132.24, 136.74, 139.49, 139.57, 139.81,
167.41, 170.51. Anal. Calc. for C20H16N2O2: C, 75.93%; H, 5.10%; N,
8.86%. Found: C, 75.80%; H, 5.44%; N, 9.03%.
d
7.17e8.76 (set of signals, 15H, aromatic protons and exchangeable
NH2); 13.05 (s, 1H, NH; exchangeable with D2O). 13C-NMR (
d)
(DMSO) 119.04, 104.16, 119.95, 122.55, 126.86, 127.05, 127.55, 128.16,
128.67, 128.98, 132.52, 133.27, 138.84, 140.06, 143.46, 163.96, 171.13.
Anal. Calc. for C20H16N2O2: C, 75.93%; H, 5.10%; N, 8.86%. Found: C,
75.82%; H, 5.13%; N, 8.77%.
4.1.7.14. N-(2-carbamoyl-4-iodophenyl)-[1,1'-biphenyl]-2-
carboxamide (17b). 30% yield; mp 152e156 ꢀC (ethanol); I.R. (KBr)
cm-1 3228, 3199, 3076 (NH, NH2), 1659, 1655 (2 CO) 1H-NMR
(DMSO)
exchangeable NH2); 11.77 (s, 1H, NH; exchangeable with D2O). 13C-
NMR ( ) (DMSO) 86.84, 122.25, 122.48, 127.85, 128.07, 128.22,
128.75, 128.80, 130.84, 130.96, 136.93, 137.04, 139.51, 139.92, 140.13,
141.04, 167.85, 169.38. Anal. Calc. for C20H15IN2O2: C, 54.32%; H,
3.42%; N, 6.33%. Found: C, 53.93%; H, 3.26%; N, 6.40%.
d 7.29e8.27 (set of signals, 14H, aromatic protons and
4.1.7.8. N-(2-carbamoyl-4-iodophenyl)-[1,1'-biphenyl]-4-
carboxamide (14b). 46% yield; mp 250e255 ꢀC (ethanol); I.R. (KBr)
cm-1 3384, 3273, 3210 (NH, NH2), 1668, 1655 (2 CO) 1H-NMR
d
(DMSO)
exchangeable NH2); 12.95 (s, 1H, NH; exchangeable with D2O). 13C-
NMR ( ) (DMSO) 86.27, 121.18, 122.21, 126.93, 127.14, 127.64, 128.26,
d 7.44e8.56 (set of signals, 14H, aromatic protons and
d
129.05, 133.07, 136.77, 138.85, 139.74, 140.94, 143.65, 164.07, 169.77.
Anal. Calc. for C20H15IN2O2: C, 54.32%; H, 3.42%; N, 6.33%. Found: C,
54.54%; H, 3.45%; N, 6.29%.
4.1.7.15. N-(2-carbamoyl-4-chlorophenyl)-[1,1'-biphenyl]-2-
carboxamide (17c). 15% yield; mp 145e147 ꢀC (ethanol); I.R. (KBr)
cm-1 3329-3150 (NH, NH2), 1682, 1646 (2 CO) 1H-NMR (DMSO)
d
7.37e8.48 (set of signals, 14H, aromatic protons and exchangeable
NH2); 11.78 (s, 1H, NH; exchangeable with D2O). Anal. Calc. for
20H15ClN2O2: C, 68.48%; H, 4.31%; N, 7.99%. Found: C, 68.77%; H,
4.1.7.9. N-(2-carbamoyl-4-chlorophenyl)-[1,1'-biphenyl]-4-
carboxamide (14c). 47% yield; mp 210e212 ꢀC (ethanol); I.R. (KBr)
cm-1 3384-3216 (NH, NH2), 1668, 1651 (2 CO) 1H-NMR (DMSO)
C
4.03%; N, 7.71%.
d
7.43e8.77 (set of signals, 14H, aromatic protons and exchangeable
NH2); 12.95 (s, 1H, NH; exchangeable with D2O). 13C-NMR (
d)
4.1.7.16. N-(2-carbamoyl-4-methylphenyl)-[1,1'-biphenyl]-2-
carboxamide (17d). 30% yield; mp 148e150 ꢀC (ethanol); I.R. (KBr)
cm-1 3342, 3159, 3059 (NH, NH2), 1677, 1641 (2 CO) 1H-NMR (CDCl3)
(DMSO) 120.72, 121.75, 126.43, 126.93, 127.14, 127.64, 128.27,
128.35, 129.05, 132.25, 133.01, 138.84, 138.97, 143.66, 164.09, 169.85.
Anal. Calc. for C20H15ClN2O2: C, 68.48%; H, 4.31%; N, 7.99%. Found: C,
68.44%; H, 4.70%; N, 7.76%.
d
2.24 (s, 3H, CH3); 5.73 (s, broad, 1H, NH-H, exchangeable with
D2O); 6.19 (s, broad, 1H, NH-H, exchangeable with D2O); 7.20e8.48
(set of signals, 12H, aromatic protons); 10.88 (s, 1H, NH;
4.1.7.10. N-(2-carbamoyl-4-methylphenyl)-[1,1'-biphenyl]-4-
carboxamide (14d). 44% yield; mp 220e222 ꢀC (ethanol); I.R. (KBr)
cm-1 3424, 3321, 3113 (NH, NH2), 1656, 1645 (2 CO) 1H-NMR
exchangeable with D2O). 13C-NMR (
d) (DMSO) 20.73, 119.43, 121.40,
127.38, 127.53, 127.66, 128.28, 128.34, 128.83, 130.33, 130.60, 132.50,
133.60, 136.58, 137.11, 140.09, 140.17, 168.40, 170.93. Anal. Calc. for
(DMSO)
d
2.32 (s, 3H, CH3); 7.40e8.66 (set of signals, 14H, aromatic
C21H18N2O2: C, 76.34%; H, 5.49%; N, 8.48%. Found: C, 76.35%; H,
protons and exchangeable NH2); 12.95 (s, 1H, NH; exchangeable
5.25%; N, 8.52%.