Synthesis, Antioxidative and Antiproliferative Activity of Methoxy Amidino Substituted

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:

1. 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.