Synthesis, antioxidative and antiproliferative activity of methoxy amidino substituted benzamides and benzimidazoles
Maja Cindrića, Irena Sovića, Irena Martin-Kleinerb, Marijeta Kraljb, Tomislav Mašekc
Marijana Hranjeca* and Kristina Starčevićc*
a Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, P. O. Box 177, HR-10000 Zagreb, Croatia
b Division of Molecular Medicine, Ruđer Bošković Institute, Bijenička cesta 54, P. O. Box 180, HR-10000 Zagreb, Croatia
c Department of Animal Husbandry, Faculty of Veterinary Medicine, University of Zagreb, Heinzelova 55, HR-10000 Zagreb, Croatia
Contents of Supporting Information:
- Figures 1S-47S are NMR spectrum of novel compounds.
Figure 1S.1H NMR spectrum of N-(2,4-dimethoxyphenyl)-2-methoxybenzamide6.
Figure 2S.13C NMR spectrum of N-(2,4-dimethoxyphenyl)-2-methoxybenzamide6.
Figure 3S.1H NMR spectrum of N-(2,4-dimethoxyphenyl)-2,4-dimethoxybenzamide7.
Figure 4S.13C NMR spectrum of N-(2,4-dimethoxyphenyl)-2,4-dimethoxybenzamide7.
Figure 5S.1H NMR spectrum of N-(2,4-dimethoxyphenyl)-3,4,5-trimethoxybenzamide8.
Figure 6S.13C NMR spectrum of N-(2,4-dimethoxyphenyl)-3,4,5-trimethoxybenzamide8.
Figure 7S.1H NMR spectrum of N-(4-cyanophenyl)-2-methoxybenzamide9.
Figure 8S.13C NMR spectrum of N-(4-cyanophenyl)-2-methoxybenzamide9.
Figure 9S.1H NMR spectrum of N-(4-cyanophenyl)-2,4-dimethoxybenzamide10.
Figure 10S.13C NMR spectrum of N-(4-cyanophenyl)-2,4-dimethoxybenzamide10.
Figure 11S.1H NMR spectrum of N-(4-cyanophenyl)-3,4,5-trimethoxybenzamide11.
Figure 12S.13C NMR spectrum of N-(4-cyanophenyl)-3,4,5-trimethoxybenzamide11.
Figure 13S.1H NMR spectrum of N-(4-amidinophenyl)-2-methoxybenzamide hydrochloride12.
Figure 14S.13C NMR spectrum of N-(4-amidinophenyl)-2-methoxybenzamide hydrochloride12.
Figure 15S.1H NMR spectrum of N-(4-amidinophenyl)-2,4-dimethoxybenzamide hydrochloride13.
Figure 16S.13C NMR spectrum of N-(4-amidinophenyl)-2,4-dimethoxybenzamide hydrochloride13.
Figure 17S.1H NMR spectrum of N-(4-amidinophenyl)-3,4,5-trimethoxybenzamide hydrochloride14.
Figure 18S.13C NMR spectrum of N-(4-amidinophenyl)-3,4,5-trimethoxybenzamide hydrochloride14.
Figure 19S.1H NMR spectrum of N-[4-(2-imidazolinyl)phenyl]-2-methoxybenzamide hydrochloride15.
Figure 20S.13C NMR spectrum of N-[4-(2-imidazolinyl)phenyl]-2-methoxybenzamide hydrochloride15.
Figure 21S.1H NMR spectrum of N-[4-(2-imidazolinyl)phenyl]-2,4-dimethoxybenzamide hydrochloride16.
Figure 22S.13C NMR spectrum of N-[4-(2-imidazolinyl)phenyl]-2,4-dimethoxybenzamide hydrochloride16.
Figure 23S.1H NMR spectrum of N-[4-(2-imidazolinyl)phenyl)-3,4,5-trimethoxybenzamide hydrochloride17.
Figure 24S. 13C NMR spectrum of N-[4-(2-imidazolinyl)phenyl)-3,4,5-trimethoxybenzamide hydrochloride17.
Figure 25S.1H NMR spectrum of 5(6)-amidino-2-(2-methoxyphenyl)benzimidazole hydrochloride23.
Figure 26S.13C NMR spectrum of 5(6)-amidino-2-(2-methoxyphenyl)benzimidazole hydrochloride23.
Figure 27S.1H NMR spectrum of 5(6)-amidino-2-(2,4-dimethoxyphenyl)benzimidazole hydrochloride24.
Figure 28S.13C NMR spectrum of 5(6)-amidino-2-(2,4-dimethoxyphenyl)benzimidazole hydrochloride24.
Figure 29S.1H NMR spectrum of 5(6)-amidino-2-(3,4,5-trimethoxyphenyl)benzimidazole hydrochloride25.
Figure 30S.13C NMR spectrum of 5(6)-amidino-2-(3,4,5-trimethoxyphenyl)benzimidazole hydrochloride25.
Figure 31S.1H NMR spectrum of 5(6)-(2-imidazolinyl)-2-(2-methoxyphenyl)benzimidazole hydrochloride26.
Figure 32S.13C NMR spectrum of 5(6)-(2-imidazolinyl)-2-(2-methoxyphenyl)benzimidazole hydrochloride26.
Figure 33S.1H NMR spectrum of 5(6)-(2-imidazolinyl)-2-(2,4-dimethoxyphenyl)benzimidazole hydrochloride27.
Figure 34S.13C NMR spectrum of 5(6)-(2-imidazolinyl)-2-(2,4-dimethoxyphenyl)benzimidazole hydrochloride27.
Figure 35S.1H NMR spectrum of 5(6)-(2-imidazolinyl)-2-(3,4,5-trimethoxyphenyl)benzimidazole hydrochloride28.
Figure 36S.13C NMR spectrum of 5(6)-(2-imidazolinyl)-2-(3,4,5-trimethoxyphenyl)benzimidazole hydrochloride28.
Figure 37S.1H NMR spectrum ofN-(5(6)-cyanobenzimidazol-2-yl)-2,4-dimethoxybenzamide30.
Figure 38S.13C NMR spectrum of N-(5(6)-cyanobenzimidazol-2-yl)-2,4-dimethoxybenzamide30.
Figure 39S.1H NMR spectrum of N-(5(6)-cyanobenzimidazol-2-yl)-3,4,5-trimethoxybenzamide31.
Figure 40S.13C NMR spectrum ofN-(5(6)-cyanobenzimidazol-2-yl)-3,4,5-trimethoxybenzamide31.
Figure 41S.1H NMR spectrum ofN-(5(6)-amidinobenzimidazol-2-yl)-2,4-dimethoxybenzamide hydrochloride32.
Figure 42S.13C NMR spectrum ofN-(5(6)-amidinobenzimidazol-2-yl)-2,4-dimethoxybenzamide hydrochloride32.
Figure 43S. 1H NMR spectrum of N-(5(6)-amidinobenzimidazol-2-yl)-3,4,5-trimethoxybenzamide hydrochloride33.
Figure 44S. 1H NMR spectrum ofN-[5(6)-2-(imidazolinyl)benzimidazol-2-yl]-2,4-dimethoxybenzamide hydrochloride34.
Figure 45S.13C NMR spectrum of N-[5(6)-2-(imidazolinyl)benzimidazol-2-yl]-2,4-dimethoxybenzamide hydrochloride34.
Figure 46S. 1H NMR spectrum of N-[5(6)-2-(imidazolinyl)benzimidazol-2-yl]-3,4,5-trimethoxybenzamide hydrochloride35.
Figure 47S.13C NMR spectrum ofN-[5(6)-2-(imidazolinyl)benzimidazol-2-yl]-3,4,5-trimethoxybenzamide hydrochloride35.