Synthesis of Some New Bis(Mannich Bases) Related to Succinimide and Benzamide and Evaluation of Their Antibacterial and Antifungal Activities
[1]
Ebrahim Abdel-Galil, Chemistry Department, Science Faculty, Mansoura University, Mansoura, El-Dakahlia, Egypt.
[2]
Norelhoda Salah Abdellatif, Chemistry Department, Science Faculty, Mansoura University, Mansoura, El-Dakahlia, Egypt.
[3]
Soha Mostafa Abdelmageed, Chemistry Department, Science Faculty, Mansoura University, Mansoura, El-Dakahlia, Egypt.
[4]
Elsayed Mohamed Afsah, Chemistry Department, Science Faculty, Mansoura University, Mansoura, El-Dakahlia, Egypt.
Treatment of Succinimide (1) with the appropriate aldehyde and amine afforded Mannich bases 2a-f, 3 and 4 and the bis(Mannich bases) 5-8. The Mannich bases 2a-fwere used as precursors in synthesis of the new mixed bis(Mannich bases) 9a-c, 10a-c, 11a,b and 12a,b. Mannich reaction of benzamide (13) and the mixed diamide 17 with the appropriate aldehyde and amine gave the Mannich bases 14-16, 18 and 19. In addition, N-amidomethylation of tetrahydrocarbazole (21) and its benzo derivative 23 with the amidic Mannich bases 20a-c afforded compounds22a-c and 24a-c, respectively.
Bis(Mannich Bases), Mixed Mannich Bases, Amidic Mannich Bases
[1]
K. L. Vine, L. Matesic, J. M. Loke, M. Ranson, D. Skropeta, Anticancer agents Med. Chem. 2009, 9, 397–414.
[2]
S. N. Pandeya, S. Smitha, M. Jyoti, S. K. Sridhar, Acta. Pharm. 2005, 55, 27-46.
[3]
M. Koksal, I. Ozkan-Dagliyan, T. Ozyazici, B. Kadioglu, H. Sipahi, A. Bozkurt, Archiv der pharmazie. 2017, 350 (9).
[4]
M. B. Winstead, K. V. Anthony, L. L. Thomas, R. G. Strachan, H. J. Richwine, J. Chem. Eng. Data. 1962, 7, 414–415.
[5]
H. Hellmann, I. Loschmann, Chem. Ber. 1954, 87, 1684-1690.
[6]
J. R. Feldman, E. C. Wanger, J. Org. Chem. 1942, 7, 31-47.
[7]
M. Sekiya, Y. Terao, Chem. Pharm. Bull. 1970, 18, 947-956.
[8]
A. Katritzky, S. Rachwal, B. Rachwal, J. Chem. Soc. 1987, 799.
[9]
H. W. Heine, M. B. Winstead, R. P. Bair, J. Amer. Chem. Soc. 1956, 78, 672-674.
[10]
S. Rybka, J. Obniska, A. Rapacz, B. Filipek, K. Kaminski, Arch. Pharm. Chem. LifeSci. 2014, 347, 1–9.
[11]
J. Obniska, K. Kaminski, D. Skrzynska, J. Pichor, Eur. J. Med. Chem. 2009, 44, 2224-2233.
[12]
K. Kaminski, J. Obniska, I. Chlebek, P. Liana, E. Pekala, Eur. J. Med. Chem. 2013, 66, 12-21.
[13]
E. M. Afsah, A. A. Fadda, M. M. Hammouda, Monatshefte für chemie-chemical monthly. 2016, 147 (11), 2009-2016.
[14]
E. M. Afsah, M. Hammouda, M. M. Abou-Elzahab, Monatsh. Chem. 1984, 115, 581-85.
[15]
E. M. Afsah, E. Abdel-Galil, I. A. Youssef, Res. J. Pharm. Biol. Chem. Sci. 2011, 2, 1066-1078.
[16]
J. Szmuszkovicz, J. Amer. Chem. Soc. 1960, 82, 1180-1186.
[17]
C. Mannich, G. Heilner, Ber. 1922, 55, 365-374.
[18]
M. Furukawa, Y. Kojima, Y. Okahara, S. Hayashi, Chem. Pharm. Bull. 1974, 22, 262-266.
[19]
H. Hellmann, G. Haas, Chem. Ber. 1957, 90, 50-53.
[20]
R. D. Haworth, R. McGillivray, D. H. Peacock, J. Chem. Soc. 1950, 1493-1498.
[21]
V. I. Stavrovskaya, S. K. Drusvyat-skaya, Pharm. Chem. J. 1967, 1, 262-263.
[22]
C. U. Rogers, B. B. Corson, Org. Synth. 1963, 4, 884.
[23]
D. Ibrahim, T. F. Nazari, J. Kassim, S. H. Lim, Appl. Pharm. Sci. 2014, 4, 1-6.
